Vacation Rentals By Owner In Southport, ME

Piffi Biff: A Large Historic Home on Southport IslandbrbrWelcome to Piffi Biff, a stunning historic cottage perched on the rugged shores of Southport Island. This expansive home offers a front-row seat to the best of the Maine coast, featuring incredible views of the Atlantic Ocean, Squirrel Island, Burnt Island, and the bustling entrance to Boothbay Harbor. Whether you are watching a pod of porpoises or an endless parade of sailboats and lobster boats, Piffi Biff provides non-stop coastal entertainment.brbrCharming FeaturesbrClassic Maine Architecture: Experience the grandeur of a historic summer cottage featuring a spacious living room centered around a magnificent field-stone fireplace.brExceptional Ocean Views: Gorgeous vistas are the hallmark of this home, visible from the living room, dining room, breakfast room, and nearly every bedroom.brRoom for the Whole Family: With five bedrooms and a flexible layout, this home is designed for multi-generational gatherings and large groups.brIndoor-Outdoor Dining: Enjoy the salt air from the covered open deck, which serves as a secondary dining area and a peaceful spot to soak in the sights and sounds of the sea.brModern Conveniences: Piffi Biff boasts a washer and dryer—a rare and highly convenient feature for a historic home located so close to the water.brExpandable Living: For those hosting large dinners, the dining table includes an additional leaf to accommodate your entire group.brbrNOTE: Traveling with a very large group Piffi Biff can be rented alongside its neighbor, Pine Cliff Dweller, to create the perfect setting for a family reunion or multi-family vacation.brbrThe Details:brbrMinimum Stay: Weekly (Saturday-Saturday) from June through September; 4-night minimum available during the fall season. Stay for a week or longer during the shoulder season to receive a better value on your booking!brbrBEDROOMS: (2) King beds, (1) Queen bed, (1) Bedroom with three Twin beds, and (1) Bedroom with a single Twin bed.brbrBATHROOMS: (1) Full en-suite with shower, (1) Full bathroom with a soaking tub and separate shower, and (1) Half bath.brbrDOGS PERMITTED Up to two adult dogs are welcome here!brbrLINENS & TOWELS INCLUDED Yes, linens and towels are included in your reservation.brbrExplore the RegionbrNature Watching: Keep your binoculars ready for whales, migratory shorebirds, and the local porpoise population right from your deck.brSouthport Island: Explore the quiet beauty of the island, including its historic bridges, local general store, and winding coastal roads.brBoothbay Harbor: Take a short drive into the harbor for world-class dining, boutique shopping, and boat excursions.brbrBook your historic island getaway at Piffi Biff today!brbrCOTTAGE CONNECTION Vacation Rentals. Privately Owned. Professionally Managed. Trusted since 1993. Cottage Connection was one of the first vacation rental companies in the Midcoast region of Maine. Since being founded by Jeff and Audrey Miller in 1993, Cottage Connection has been trusted by homeowners and vacationers alike to connect each family with the perfect vacation cottage.

Cabin

Piffi Biff: Watch Whales & Lobster Boats from This Classic Oceanfront Gem!

Southport, Maine, United States

Bed

Bath

Sleeps

$235.48

Located on Southport Island, we are near the water, and adjacent to Capitol Island. This detached garage apartment is spacious and great for couples or solo adventurers.brbrThis is an open plan apartment with kitchen, dining and living spaces connected. There is a private bathroom and one bedroom with a queen bed. We have a sofa and also a modern sofa bed/futon as well as an air mattress. We recommend that the additional sleeping accommodations be used for children or short term guests. We also have a pack-n-play crib available to renters.

Apartment

Boothbay Open Plan 1- Bedroom Apt. Woods & Water. Southport.

Southport, Maine, United States

Bed

Bath

3

Sleeps

$536.81

Pine Cliff Dweller: Classic Coastal Comfort and Panoramic ViewsbrbrPerched on a cliff overlooking the entrance to Boothbay Harbor and the islands of the Atlantic, Pine Cliff Dweller is a treasured family home ready for your next memorable Maine vacation. This cozy, traditional cottage serves as a popular home base for both adventurers and those seeking a quiet retreat, offering a warm and inviting atmosphere that feels like a true home away from home.brbrCharming FeaturesbrPanoramic Ocean Vistas: Watch the world go by from the dining room, which features three walls of windows overlooking the ocean, your private dock, and surrounding islands.brClassic Maine Ambiance: Enjoy the cozy feel of this non-minimalist retreat, complete with a working, wood-burning fieldstone fireplace that serves as the heart of the home.brMaster Suite with A/C: The second-floor master bedroom features a king bed, panoramic views, and air conditioning to ensure comfort on warm summer nights.brPrivate Dock and Float: Witness the activity of the harbor firsthand, from elegant yachts to hardworking lobster boats. You may even spot porpoises, migratory shorebirds, or the occasional whale. Love fresh seafood You can connect with local lobstermen for dockside service right on your private dock!brInviting Living Spaces: The open layout is filled with natural light thanks to large windows and sliding doors, making it easy for guests to gather in the family room or living area.brPerfect for Groups: With a bedroom and full bathroom on each floor, this home is ideal for two couples or small families. For larger gatherings, the neighboring cottage, Piffi Biff, can be rented in conjunction for a multi-family getaway.brbrThe Details:brbrMinimum Stay: Weekly (Saturday-Saturday) during June, July, and August; 4-night minimum in the Fall. Stay for a week or longer during the Fall to receive a better value on your booking! BEDROOMS: (1) King (Master with A/C), (1) Queen. BATHROOMS: (2) Full bathrooms, both featuring tub/shower combinations. DOGS PERMITTED No, pets are not allowed at this property. LINENS & TOWELS INCLUDED Yes, linens and towels are included in your reservation.brbrExplore the RegionbrSouthport Island Exploration: Discover the quiet charm of the island, including the Southport General Store, Hendrick's Head Beach, and the scenic views along the shore.brIconic Sightseeing: From the cottage, you have a front-row seat to views of Burnt Island and Squirrel Island.brBoothbay Harbor Entrance: Enjoy being at the gateway of the region's most famous harbor, just a short drive from downtown shops and restaurants.brbrBook your classic Maine retreat at Pine Cliff Dweller today!brbrCOTTAGE CONNECTION Vacation Rentals. Privately Owned. Professionally Managed. Trusted since 1993. Cottage Connection was one of the first vacation rental companies in the Midcoast region of Maine. Since being founded by Jeff and Audrey Miller in 1993, Cottage Connection has been trusted by homeowners and vacationers alike to connect each family with the perfect vacation cottage.

PINE CLIFF DWELLER | 2 Bed, 2 Bath

Southport, Maine, United States

Bed

Bath

Sleeps

$174.4

The White Cottage is located on Decker's Cove overlooking a busy waterway with lots of boat traffic. Lobster wharf + restaurant across the street with 20 local lobstermen bringing in their catch. Small yard with picnic table & umbrella and out door chairs. Kitchen fully equipped, Free WIFI, cable TV, linens. Two miles from downtown Boothbay Harbor, shopping, boat rides, restaurants, & best Botanical Garden in the Northeast.

3 one-bedroom fully equipped cottages with free WIFI /weekly rental

Southport, Maine, United States

Bed

Bath

Sleeps

$174.4

The Dockside Cottage is located on Decker's Cove overlooking a busy waterway with lots of boat traffic. Lobster wharf + restaurant across the street with 20 local lobstermen bringing in their catch. Deck with picnic table & umbrella and out door chairs. Kitchen fully equipped, Free WIFI, cable TV, linens. Two miles from downtown Boothbay Harbor, shopping, boat rides, restaurants, & best Botanical Garden in the Northeast.

3 one-bedroom fully equipped cottages with free WIFI /weekly rental

Southport, Maine, United States

Bed

Bath

Sleeps

$174.4

The Tan Cottage is located on Decker's Cove overlooking a busy waterway with lots of boat traffic. Lobster wharf + restaurant across the street with 20 local lobstermen bringing in their catch. Small yard with picnic table & umbrella and out door chairs. Kitchen fully equipped, Free WIFI, cable TV, linens. Two miles from downtown Boothbay Harbor, shopping, boat rides, restaurants, & best Botanical Garden in the Northeast.

3 one-bedroom fully equipped cottages with free WIFI /weekly rental

Southport, Maine, United States

Bed

Bath

Sleeps

$388.54

Welcome to your coastal escape! This 3-bedroom, 1.5-bath waterfront home is tucked away on Southport Island, a hidden gem in Maine’s Boothbay region. Known for its scenic beauty and maritime heritage, Southport offers a peaceful, authentic coastal experience while keeping you close to the shops, dining, and activities of nearby Boothbay Harbor.brbrThe HomebrbrPerfect for families, small groups, or couples traveling together, this home comfortably sleeps six guests. Inside, you’ll find:brbrThree cozy bedrooms and 1.5 bathroomsbrbrA fully equipped kitchen for preparing fresh local seafood dinners or simple family mealsbrbrAn open dining room/living area with space to relax, play games, or curl up with a book.brbrStep outside and the real magic begins. The property sits right on the water, offering a front-row seat to the tides and Maine’s ever-changing coastal views. Start your morning with coffee overlooking the shoreline, enjoy picnics by the water, or spend evenings stargazing in the quiet salt air.brbrThe LocationbrbrSouthport Island is the perfect blend of serenity and adventure. Connected to Boothbay Harbor by a historic swing bridge, the island offers easy access to local attractions while keeping you tucked away in a more tranquil setting. brbrGuests can enjoy:brbrBoating, kayaking, and paddle boarding right from the island.brbrNature walks and hikes through pine forests and along the rocky coast.brbrLocal beaches and landings, perfect for a summer swim or simply soaking up the view.brbrFresh lobster and seafood from local shacks and markets.brbrA quick drive to Boothbay Harbor, where you’ll find boat tours, shopping, galleries, and family-friendly attractions like the Coastal Maine Botanical Gardens.brbrPet-Friendly StaybrbrWe know vacations are better with the whole family, which is why your pets are welcome here. There’s plenty of space for them to enjoy the fresh air right alongside you.brbrWhether you’re seeking outdoor adventure, a quiet coastal retreat, or a little of both, this Southport Island waterfront home is the perfect place to make lasting Maine memories.brHouse Rules & Helpful Infobrbr-Fireplace: Please DO NOT use the fireplace!brbr-Trash & Recycling: Please remove all trash, including any food left in the fridge, and place bagged trash in the outdoor bins.brbr-Recycling does not need to be sorted, except for bottles and cans that are refundable in Maine. These can be set aside—feel free to return them to a local redemption center, or housekeeping will collect them.brbr-No Smoking: Smoking is not permitted anywhere inside or outside on the property.brbr-No Fireworks: Fireworks are strictly prohibited on the premises.brbr-Damage Policy: Accidents happen—please report any damage promptly so we can address it quickly. The Damage Waiver covers unintentional damage to the property and its contents up to $1500, provided damages are reported to Ohana Vacations before check-out. (Airbnb reservations excluded)brbr-Starter Pack: Ohana provides a starter supply of essentials (toilet paper, paper towels, soap, etc.). Guests are responsible for replenishing the following items as needed.brbrThese items ARE NOT included...brbr-Spices & condimentsbrbr-Mosquito/tick repellentbrbr-Personal hygiene itemsbrbr-Sunscreenbrbr-Beach towelsbrbrGrill Use: If a grill is available, please do not move it and keep it 5–10 feet from the house at all times. Kindly clean the grill after each use.brbrIf propane runs out, please contact Ohana customer service for a replacement.brbrPrivate Wells & Septic Systems: Some of our homes use private wells and septic systems. brbr-Please: Flush only toilet paper—no wipes, feminine products, or other items.brbr-Avoid driving on the lawn, as pipes run underground.brbr-Be mindful of water usage.

Waterfront Retreat on Southport Island - Pet-Friendly, Sleeps 6

Southport, Maine, United States

3

Bed

Bath

6

Sleeps

$440.46

Mid-Century Modern Charm on the Waterfront!brbrDiscover the charm of coastal Maine at Cedarbush Cabin, a classic mid-century modern waterfront cottage with stunning views and relaxed vibes. Enjoy your morning coffee or evening cocktail from the deck as boats glide by, or head down to the dock and float for a closer look at the bay.brbrThis single-level cabin features two bedrooms and two full baths, a well-equipped kitchen, a cozy living room with a fireplace, and a dining area with seating for up to eight—perfect for gathering after a day of seaside adventures.

Cedarbush Cabin - Waterfront Cottage - walk to Robinson's Wharf!

Southport, Maine, United States

Bed

Bath

4

Sleeps

$615.08

Your cozy getaway awaits in Southport at this lovely house. With three bedrooms featuring two queen beds and a twin bed, there’s plenty of space for guests to relax. The three bathrooms add convenience for everyone in your group. A soothing office area includes a comfortable sofa bed, perfect for work or extra sleeping space. Heating keeps the atmosphere warm and inviting throughout your stay. Whether you’re unwinding after a day of exploring or enjoying quiet moments inside, this gorgeous home offers a peaceful retreat. We look forward to welcoming you to our place.

Waterfont Southport, Maine Cottage - Beautifully appointed 3-bedroom getaway

Southport, Maine, United States

Bed

Bath

Sleeps

$1030.0

Miradon Ocean Estate affectionately known as “Ole Gusty”, is an extraordinary oceanfront retreat. Designed to showcase panoramic sunsets, the home boasts ocean views that are best enjoyed from the expansive deck. Hosted by Of Sea and Pine; Maine Vacation Rentals, Miradon is located on the enchanting island of Southport, just a stone’s throw from Boothbay Harbor. The original owner was an artist and her keen eye can be found not only in the unique décor of the home, but also in her artwork displayed throughout. Her passion for cooking and hosting inspired the open-concept kitchen, which serves as the heart of the home. Her favorite cookbooks still line the kitchen counter, many with tabs marking her preferred recipes. With over 3500 square feet of living space, including 4 bedrooms, 3 bathrooms and 6 beds, this home is truly an oasis for family and friends to gather. Sleeps 8 adults. brbr Key Features:br-Spectacular views! Enjoy ocean views throughout the home. br-The open flow of the main floor is sure to inspire conversation and laughter as you enjoy coffee in the sunroom, play games in the living room, and cook meals together in the kitchen before lingering over them in the beautiful dining room.br-Stone firepit overlooking the ocean; after dinner gather around the firepit to roast marshmallows, tell stories and star gaze. br-Multiple deck spaces perfect for morning coffee or evening relaxation br-Primary bedroom with king bed and ensuite with a soaking tub and walk in showerbr-Enchanting artist's turret, beckoning creativity and inspiration (where much of the artwork in the home was created!) br-Water views and access to the rocky beach* br-Private yard brbr*Please Note: There is no water access - not conducive to swimming- there is a public beach nearby. No dogs are allowed at this property. This is a fairly remote location, a vehicle is needed to access the home and surrounding areas; Uber does not operate in the area. brbr Home Layout: brMain level – two bedrooms each with a full-size bed. Full bathroom with a walk-in shower. brSecond Floor – primary bedroom with king bed and ensuite with soaking tub and walk in shower; second bedroom with a queen bed and ensuite with walk in shower; two twin-size daybeds on the second-floor landing. brPlease be aware, there is no air conditioning at this property. There are fans in every room & opening windows in the evening is sufficient to cool the home. brbr♿ Accessibility: There are a few steps to enter the home, once inside the main level is step free, there are two smaller bedrooms downstairs and a walk in shower. brbr Parking: Parking for up to 6 cars in the driveway brbr Location & Local Charm: brThe slower pace of island life inspires leisurely exploration. Take a walk down to the Southport Library, where you’ll find cozy reading nooks and local artwork on display. Venture a bit further to the town landing to see Margaret Hamilton’s red summer cottage (she played the Wicked Witch of the West in The Wizard of Oz) on neighboring Cape Island.brbrStop by the Southport General Store for a sandwich, then head to Hendrick’s Head Beach for a swim and views of the local lighthouse. If you’re in the mood for a more bustling coastal town, drive over the swing bridge that connects Southport to the mainland and visit the quintessential village of Boothbay Harbor. Grab a fresh cup of coffee from Red Cup, then explore the many unique shops, discovering treasures along the way.brbrLooking to get out on the water The Lazy Jack sailing tour is a favorite, and the Clam Bake at Cabbage Island is certainly a treat. End the day by dining at the Thistle Inn, but be sure to return in time to catch the sunset at “Ole Gusty” with a glass of wine — it’s truly heaven!brbr Things to Do NearbybrOther nearby attractions include the Coastal Maine Botanical Gardens, the Maine State Aquarium, the Railway Village Museum, and the Boothbay Harbor Country Club. Take a scenic drive up the coast to explore popular destinations such as Damariscotta, Camden, and Rockland. A complete guidebook will be provided with these and other area attractions.

Miradon Ocean Estate: Expansive Ocean Views

Southport, Maine, United States

Bed

Bath

Sleeps

$681.25

Only 12 minutes from Coastal Maine Botanical Gardens, home of Gardens Aglow. Welcome to this modern architectural gem tucked among the spruces on Southport Island, serenely peaceful and yet just a few minutes from Boothbay Harbor. The house is full of fun angles and expansive windows and is cantilevered over a granite ledge; think Frank Lloyd Wright meets Dr. Seuss.brbrThe house boasts two master suites (one 1st floor, one 2nd floor), a bunk room with five twin beds and a fourth Queen bedroom. There are three and a half luxurious baths.brbrIn June 2023 we completed a 18-month, down-to-the-studs renovation. Every surface is new for you to enjoy.brbrThe first floor -- kitchen, great room, a master bedroom with en-suite bathroom and a wrap-around deck with distant water views -- is accessible for anyone with mobility issues; there is just one small step to get in the house.brbrUpstairs there is laundry, a second master bedroom with an en-suite bathroom + its own private deck, a bunk room with five twin beds, a delightful bedroom for two and a shared bath off the hallway.brbrThe kitchen is fully equipped for cooking a feast and the dining table can seat 12.brbrThe house is fully air conditioned. Gas grill on the deck, lawn games including corn hole and a smokeless fire pit. Lots of outdoor seating on the various decks and around the fire. The property also has a lovely moss-covered forest that is the perfect spot for children to build fairy houses.brbrThe ocean is a short walk away, and you will have access to a delightful pebble beach.brbrSouthport is known for its peace and quiet, its bold oceanfront and proximity to the many restaurants, shops and galleries five minutes away in Boothbay Harbor. brbrSouthport also has its own sandy beach, three waterside restaurants, a lobster pound with seating right on the dock and a charming general store known for its wine selection and pizza.brbrHave kids Sign them up for a week of the youth Sailing Program at the Southport Yacht Club. Our kids do this and we can't recommend it enough!brbrWe are located 7 minutes from Boothbay Harbor, 10 minutes from the Coastal Maine Botanical Gardens and 5 minutes from Hendrick's Head Beach.

Boothbay area -- Newly renovated, near ocean, short drive to Botanical Gardens

Southport, Maine, United States

Bed

Bath

Sleeps

$261.69

Escape to a fabulous 3-bedroom cottage in Southport. This welcoming retreat features a queen bed, bunk bed, twin bed, and king bed, perfect for a cozy getaway. With amenities like WiFi, a washing machine, heating, and AC, guests can relax and unwind. The three bathrooms offer a bathtub for a soothing soak after a day of exploring. brbrOutside you'll enjoy a near-wrap around deck with fire feature and direct views of Christmas Cove, an inlet with direct access to the Atlantic Ocean. A manicured path off the driveway leads to the waterfront street where a cozy bench and kayaks await you. Close to the great coastal town of Boothbay but secluded at the end of a long private driveway. Fall in love with Southport and enjoy the magic it has to offer.

Charming 3-bedroom cottage in Southport with water views and close to Boothbay.

Southport, Maine, United States

Bed

Bath

Sleeps

$627.52

Let it all go! Come here for peace and respite. Welcome to quintessential Maine summer living! Enjoy stunning ocean views and cool summer breezes at this very private and quaint seasonal home! This is a very comfortable, cozy, and classic retreat that is newly painted with new furnishings and is well appointed for your vacation needs. All bedrooms have new mattresses and bedding that will ensure a good night's sleep. Living room has a new large sectional. Linens and bath towels provided. Bring your own beach towels. Sip your morning coffee or have a picnic lunch in Adirondack chairs on the accessible rocky ledge. A covered deck offers shade without losing the sights and sounds of the coastal magic. Two chaise lounge chairs as well as two tables for outdoor eating are additional options for outdoor enjoyment. Four bicycles are available to be shared amongst guests at Cedarbush Stuga and our other vacation rental, Cozy Harbor Stuga. Please bring your own helmets. Beach chairs are available for guest use that are stored in garden shed.brbrWalk or bike to scenic Hendrick's Head Beach, a beautiful sandy beach with a small climbable outcrop called Kitten Island, in 5 minutes where you can swim, build sandcastles and explore tide pools at low tide. The Southport General Store, a local gathering spot with outdoor picnic tables, is also a 5 minute walk and offers not only breakfast pizzas, deli sandwiches and baked goods, but a carefully curated stock of hand-picked wines, beers, and ciders and more. For a leisurely wooded landscape walk, explore Hendrick's Head Preserve with an easy 1/2 mile loop for bird watching and nature photography. Shopping, restaurants, boat tours and more summer activities are a 12 minute scenic drive to Boothbay Harbor across the historic Southport Swing Bridge. A visit to the Coastal Maine Botanical Garden, the largest botanical garden in New England, is a must see as you will experience the exquisite beauty of Northern coastal horticulture and the giant trolls! brbrImportant Details:brCheck in 5:00PM. Strict check out at 10:00AM.brLinens and bath towels provided. brPlease bring your own beach towels. brbrOur property on Southport Island is exceptionally beautiful and is only 90 minutes from Portland. Come create memories at this spectacular setting. This is Maine at its best!

Solitude abounds at this idyllic Southport OCEANFRONT home-5 mins from the beach

Southport, Maine, United States

Bed

Bath

Sleeps

$454.58

The Cottage at Island Point – Southport Island, Maine. Hosted by Of Sea and Pine, Maine Vacation RentalsbrbrCome experience the charm of coastal island living at this serene Southport cottage. Nestled in the peaceful Newagen community, The Cottage at Island Point feels like stepping into an Edward Hopper painting—where life slows down, sea breezes fill the air, and the soothing sound of buoy bells will be your evening soundtrack.brbrThis inviting retreat sleeps six, with ocean glimpses from every bedroom and multiple outdoor spaces to enjoy Maine’s natural beauty. The outdoor dining area is perfect for a quintessential lobster bake under the stars. This is truly “The Way Life Should Be.”brbrPlease note: This is a fairly remote location. A vehicle is needed to access the home and surrounding areas; Uber does not operate in the area. There are no dogs allowed at this property. brbr Key Features:brMultiple Outdoor Spaces, including a firepit, balconies and a furnished dining areabrPeaceful and welcoming community atmosphere. Easy access to Newagen Seaside Inn, Southport Yacht Club, Hendrick’s Head Beach and downtown Boothbay Harbor brbr Home Layout: br• Primary Bedroom: King bed with peeks of the water br• Second Bedroom: Two twin bedsbr• Third Bedroom: Two twin bedsbrBathrooms:br• 2 Full Bathrooms (both located upstairs)bro One with a stand-up showerbro One with a bathtubbr*Please note, there is no air conditioning at this property br br♿ Accessibility: All bedrooms and bathrooms are located on the second floor, accessible only via a steep and narrow staircase. This property may not be suitable for guests with mobility limitations.brbr Parking: Free off-street parking is available for 2–3 vehicles.brbrNeighborhood Note: This cottage is located in a friendly, close-knit neighborhood with other cottages nearby. You may hear and see neighbors in their yards, children playing, or dogs barking. Guests are kindly asked to respect quiet hours between 9:00 PM and 7:00 AM.brbr Location & Local Charm: brLocated at the southern tip of Southport Island in the charming village of Newagen, this cozy cottage offers the perfect blend of tranquility and proximity. Though you may feel like you’re at the edge of the world, you're just a short drive over the iconic swinging bridge to the vibrant harbor town of Boothbay, known for its restaurants, boutique shops, art galleries, boating excursions, and ice cream parlors.brbr Things to Do Nearby: brStroll to Town Landing Pier with your morning coffee and take in the views of Cuckolds Light Station and Cape IslandbrbrMake reservations for the Newagen Inn’s lobster bakebrbrSpend a quiet afternoon at the Southport LibrarybrbrTour the Newagen Alpaca FarmbrbrPack a picnic from the Southport General Store and head to Hendricks Head Beach, where another iconic Maine lighthouse awaitsbrbrEnjoy dinner with a view at Robinson’s Wharf or Cozy’s DocksidebrbrVisit the Coastal Maine Botanical Gardens and see the magical giant trollsbrbrPlay tennis or pickleball with a day pass at the nearby YMCAbrbrA complete guidebook will be provided at booking, filled with recommendations for day trips, dining, and local activities. Need help planning Just ask—we’re happy to help you find your happy place in Maine.

Cottage at Island Point; Charming Coastal Retreat

Southport, Maine, United States

Bed

Bath

Sleeps

$638.42

Beautiful oceanfront home with large outdoor deck facing the water for dining and relaxing, Great sunsets. Private sandy beach close.brDock and kayaks available. brNear Boothbay Harbor for dining, shopping and boat excursion. Hop a ride to Monhegan Island for the day. Boothbay Gardens 10 minutes away.

Oceanfront home

Southport, Maine, United States

Bed

Bath

Sleeps

$258.88

On the water with deepwater dock for your boat - this location cannot be beat. This cottage is located on Southport Island, a short five-minute drive from the hustle and bustle of Boothbay Harbor. It is perched on the edge of Townsend Gut with water views from every room. You could easily spend the entire day watching the swing bridge open and close for the boats traveling past. Robinson’s Wharf (the island’s most popular restaurant) is a short walk away. The cottage underwent a full renovation in early 2018 and is ready for visitors!brThe cottage has an open floor plan with the kitchen opening into the living room. The large bedroom has 1 queen bed and an attached bathroom. This quaint brcottage has all you need for a quiet vacation on the water. brThe property is stunning with new professional landscaping and ample space for lawn games or lounging under the large trees while watching the tides rise and fall. There is a dock right on property for those who wish to bring their boat. On those busy summer days you'll hear the noise of the cars crossing the swing bridge.brSouthport Island is only a 5 minute drive from downtown Boothbay Harbor – just over the Townsend Gut Swing Bridge. Southport Island is close enough to Boothbay but also has its own restaurants and sites to see. Robinson’s Wharf, Cozy's Dockside and Newagen Inn are highly recommended restaurants on the island. Hendricks Head Beach is located on the west side of the island. Sailing, boating and kayaking are spectacular activities in and around the island. If you want to venture off the island, the Boothbay Harbor Region has extensive nature trails, lake swimming (Knicker Bocker Lake), golfing, an aquarium and one of the best Botanical Gardens in the country. brbr**you can also rent the 4 bedroom house on the property if you need more space. VRBO listing # 1379766. Contact Kim for more info**

Updated Cottage on Water’s Edge with Deepwater Boat Dock!

Southport, Maine, United States

Bed

Bath

Sleeps

$844.12

Unwind on Southport at this lovely cottage. With four cozy bedrooms featuring a queen bed, two full beds, and a twin bed, there’s plenty of space for guests to relax. One full and one half bathroom add convenience. The cottage stays warm and inviting thanks to its heating, making it a cool retreat no matter the season. Whether you’re gathering indoors or exploring nearby, this amazing spot offers a comfortable home base. Enjoy all that Southport & Boothbay Harbor have to offer when you stay at our place. Close to the Botanical Gardens, downtown Boothbay Harbor, Located on a quite dead end street

Serene Southport Island: Private dock, spectacular views, near Boothbay Harbor.

Southport, Maine, United States

4

Bed

Bath

7

Sleeps

$201.65

Located on Southport Island, this cottage is a dream for travelers looking to enjoy the slower pace of life. Sip your morning coffee on the wraparound deck with a view of the ocean and enjoy a book or puzzle at night next to the wood-burning fireplace. Our cottage offers a cozy retreat tucked away in the forest; you'll love being able to unwind at our beloved family vacation home. Keep an eye out for summer fireflies flitting about at twilight!brbrWhen you're ready to wander afield, the famed Boothbay Harbor is a short 10-minute drive away with plenty of boutique shops, restaurants, local saltwater taffy, boat tours, and more! You'll also want to check out the nearby Coastal Maine Botanical Gardens and Maine State Aquarium for some local daytime activities.

Charming Two-Bedroom Ocean-View Cottage in Quiet Southport

Southport, Maine, United States

Bed

Bath

Sleeps

$1261.28

Exquisitely maintained 5 bedroom/2 bathroom cottage right on the ocean. Family owned since 1891. Step back in time into a cottage furnished with antiques and historical items from Maine. Incredible views of the ocean on all sides. Spacious bedrooms, clawfoot tub, indoor and outside shower, huge eat in kitchen stocked with cookware of all kinds, a beautiful wrap around upper deck with lounge chairs for views of the sunrise over the ocean, a sunlit cozy reading nook stocked with books, steps from a private beach cove and dock to swim, at the private end of a beautiful drive-on island with a tennis and pickleball court, and an historic casino building. All this is just a short drive into Boothbay Harbor for dining & nightlife, boat tours, shopping and fun. This cottage has been a treasure for our family and I am finally opening it up for some responsible and respectful folks.

Ocean front cottage on a drive-on island in Boothbay Harbor, Maine

Southport, Maine, United States

5

Bed