Home Vacation Rentals By Owner In Windham, ME

Showing 20 Of 62 Vacation Rentals
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Exceptional(4)

$836.76

/ Nightly
Private Vacation Home

Luxury Lake House w/ Home Theater, Hot Tub & Gym

Windham, Maine, United States

Summary:brbrThis modern 4-bedroom retreat offers a private lake escape with resort-style features just steps from the water. From a saltwater hot tub under the stars to a theater-style game room and a fully equipped home gym, every space is designed for comfort, style, and play. With exclusive water access, premium amenities, and a quiet neighborhood setting, it's the perfect getaway for families, couples, or small groups.brbrbrbrThe Space:brbr• Sleeps 10: 4 private bedrooms + queen air mattressbrbr • Private water access: Just a short walk to the dock from the housebrbr • Saltwater hot tub: Outdoor spa for all-season soakingbrbr • Movie room + game table: Theater seating & big screenbrbr • 2 kayaks + 2 paddleboards: Life vests includedbrbr • Full kitchen: Premium appliances + cookwarebrbr • Outdoor fire pit: Ideal for evenings by the lakebrbr • Home gym: Fitness gear for your daily routinebrbr • Washer & dryer: For extended or active staysbrbr • Free driveway parking: Ample space for guestsbrbr • Quiet, upscale neighborhood: Tranquil and privatebrbrbrbrMore about the spacebrbrBuilt in the last 10 years, this home blends modern design with thoughtful amenities to create a comfortable, resort-like atmosphere.brbrbrbrBedrooms & Sleeping Setupbrbr • Bedroom 1: King bed (primary suite)brbr • Bedroom 2: Queen bedbrbr • Bedroom 3: Queen bedbrbrAdditional sleeping: Queen-size air mattress with full-height design and linensbrbrAll bedrooms are tastefully furnished with fresh linens, comfortable mattresses, and storage space.brbrbrbrBathroomsbrbrModern and well-appointed with premium fixtures, including:brbr • Bathroom 1: Shower + bathtub combobrbr • Walk-in shower in primary ensuitebrbr • Bathroom 3: Neo-Angle Shower Kitbrbr • Towels, shampoo, and body wash providedbrbrbrbrKitchen & DiningbrbrThe fully equipped kitchen includes:brbr • Full-size refrigerator, stove, microwave, and dishwasherbrbr • Drip coffee maker & Keurig, cookware, and serving warebrbr • Open layout ideal for group cooking and entertainingbrbr • Dining area seats your group comfortably for meals or gamebrbrbrbrTheater & Game RoombrbrA dedicated lower-level entertainment space with:brbr • Big screen TV and theater-style seatingbrbr • Game table for cards or board gamesbrbr • Cozy lighting for a cinematic vibebrbrbrbrHome Gymbrbr • Stay active during your stay with access to high-quality fitness equipment, perfect for morning workouts or rainy-day movement.brbrbrbrOutdoor Amenitiesbrbr • Saltwater hot tub: Private and peacefulbrbr • Fire pit area: Surrounded by Adirondack seatingbrbr • 2 kayaks + 2 paddleboards: With life vests for guestsbrbr • Deck & lawn space: Relax, dine, or play outdoorsbrbrbrbrLocal AttractionsbrbrThis home offers easy access to the best of the region:brbr • Maine Path & Paddle Guide's: Swim, paddle, or float just steps awaybrbr • Maine Wildlife Park: 10 minutes by car (3.4 miles). Wildlife sanctuary featuring Maine animals such as moose, bears, and eagles.brbr • Seacoast Adventure: 5 minutes by car (2–3 miles). Seasonal fun with mini-golf, go-karts, snow tubing, and more.brbr • Donnabeth Lippman Park: 9 minutes by car (4 miles). 123-acre park with walking trails, playground, and pond.brbr • Dundee Park: 8 minutes by car. Riverside beach with picnic areas, grills, and recreation courts.brbrbrbrGuest Access:brbrGuests have full private access to the entire home and all on-site amenities, including:brbr • 4 bedrooms + queen air mattressbrbr • 2 full bathroomsbrbr • Kitchen, dining, and living spacesbrbr • Movie/game room & home gymbrbr • Saltwater hot tub, fire pit, and water gearbrbr • Private driveway parking (garage not included)brbr • Smart lock entry with personalized code provided before check-inbrbrbrbrOther Things to Note:brbr• Essentials provided: Linens, towels, shampoo, body wash, paper goods, and coffee filtersbrbr • Washer & dryer available for guest usebrbr • No crib or children’s gear is providedbrbr • 4WD recommended in winter months for snowy conditionsbrbr • Please respect quiet hours from 10 PM to 7 AM to ensure a peaceful stay for allbrbr • Our home is a smoke-free environment. This is to keep the space fresh for all guests.brbrbrbrAdditional Note: For reservations of 29 nights or longer, a security deposit will be required. This is a standard policy for extended stays and helps cover any potential damages or excessive wear and tear. The deposit will be collected prior to check-in and is fully refundable after your stay, provided the property is left in good condition. We appreciate your understanding and cooperation, and we look forward to hosting you.brbrbrbrSecurity Deposit: $1550brbrbrbrInteraction with Guests:brbrIf you need anything during your stay, don’t hesitate to reach out, we're here for you! You can message us here on Airbnb, or if you prefer, feel free to give us a call—we’re here to help however we can. We want to make sure you have a relaxing and enjoyable stay, so please let us know if there’s anything we can do!brbrbrbrWarmly,brbrRise & Shine Retreats Team
Bed 4

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Bath 3

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Sleep 10

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Exceptional(10)

$512.3

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Private Vacation Home

The Lookout on Pettingill Pond - waterfront house, 5 min from Sebago Lake!

Windham, Maine, United States

Make your getaway to Maine one for the books with a stay at our place on Pettingill Pond in Windham. brbrThis charming little 3-story house is bigger than it looks, with three bedrooms, two bathrooms and a finished walkout basement. There are 2 queen beds, 1 king bed, a set of twin-over-twin bunk beds and 1 extra twin bed, perfect for families and groups of friends alike. brbrEnjoy waterfront access and beautiful views overlooking the pond from almost anywhere in the house. With amenities like a washer & dryer, full kitchen, WiFi, and two smart TVs, come relax and enjoy our home away from home any time of the year.brbrThe open-concept living area features an eat-in kitchen, comfy sectional sofa and dining area. The house has two full bathrooms including a bathtub. The downstairs game room includes a pool table, board games, an arcade machine and a dart board for extra fun. brbrDuring the summer months, we have a dock, a hot tub and two kayaks available for use. Although it isn't an ideal place to swim, we hear there is great fishing in the pond! Dogs are always welcome. brbrPlease note, the house is located on the corner of a very busy road. There is minimal traffic noise inside the house, but it is very noticeable when outside.brbrThe house offers close proximity to shopping, restaurants and amenities in North Windham, only a 5-minute drive away. Tassel Top is a great little beach on Sebago Lake, also only a 5-minute drive from the house. Seacoast Adventure Park is right across the street and provides year-round fun for all ages, with go-karting and mini golf during the summer and snow tubing during the winter. The Deckhouse Tavern is part of the park as well and has great food and drinks. We are 40 minutes from everything Portland has to offer and 40 minutes from skiing at Shawnee Peak.
Bed 4

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Bath 2

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Sleep 10

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Exceptional(17)

$688.86

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Cottage

Little Sebago Lake - Private Sandbar With A White Sand Beach - Full Sun

Windham, Maine, United States

Grandview Point offers you an opportunity to enjoy a traditional Maine Lake experience in an updated summer cottage established in 1924. The Lake offers 9 miles of pristine water protected by the Little Sebago Lake Association for water, sand, vegetation, fish, and wildlife quality. There are three basins that make up the miles of water to explore, the middle basin of the lake has a public boat ramp where you can launch your boat and moor it on Grandview Point’s dock. Near the cottages dock there is a canoe and a rowboat with life preservers for your use; each person is required to wear a preserver in the State of Maine. The cottage is surrounded by three sides of water with a private sandy-bottomed beach in a cove and has a gradual entry that is safe for swimming. From the beach you have a view of “The Narrows” which enters back into the middle basin. The lake is stocked with brown/rainbow trout and bass by Maine’s Inland Fisheries. Five-pound bass have been caught off Grandview’s dock, just a note: A Maine fishing license is required for each person. A permit can be purchased from the Town of Windham or at the local Walmart that is 2-3 miles from cottage. The beach has full-sun all day with some birch trees if you prefer shade, there under the birch trees you will find four lounge chairs that can be moved about. On the beach closer to the cottage is a gas fire pit with four adirondack chairs; we supply one full tank of propane for your visit. There is also a gas grill with one full tank of propane.brbr Grandview Point is a two story summer cottage, the first floor has a fully stocked kitchen: refrigerator, stove/oven, microwave, toaster, blender, coffee pot, Keurig, pans, lobster pots, grilling utensils, dish soap, dish/hand towels, cleaning supplies, a dining room, and a living room with fireplace. Off the living room is a porch with an eight-foot picnic table that looks out onto the beach and lake; this is where everyone gathers for meals. The second floor has four bedrooms with the bathroom. There are two rooms that have king-size iron beds, and two rooms with queen-size iron beds. The beds have allergy covers on the mattresses and pillows, a mattress pad, and sheets with a comforter. The bathroom has a hand towel, soap, and cleaning supplies, you will need to supply bath/beach towels. Each of the rooms is finished with pine board floors, walls, and pine board ceilings with a ceiling fan. There are antique bureaus and decor that keeps with the original charm of the cottage. brbr Grandview Point is also conveniently located in the town of Windham. You will find that a 2-3 mile drive will bring you onto route 302 where there are super markets, restaurants, laundry, movie theater, amusement park with miniature golf, and an 9-hole golf course on Frye Island, Sebago Lake. A 10 mile drive will bring you to the town of Gray that has a wildlife sanctuary, 18-hole golf at Spring Meadow Golf Course, and access to route 95 that can bring you further north or south. A 20 mile drive east will bring you to Freeport with shopping at LL Bean and outlets, Wolfe’s Neck Woods State Park, and the Desert of Maine, and a 25 mile drive east will bring you to the city of Portland with it’s ocean views, wooden wharves, traditional lobster/clambakes, fine dining, shopping in the Old Port historic area, and many cultural events. brWhen making a reservation the payment should be made by e-check.
Bed 4

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Bath 1

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Sleep 8

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Exceptional(26)

$1131.39

/ Nightly
Private Vacation Home

PRIME TIME - JULY SAVE UP TO 1000.00/WEEKnCANCELLATION OPENINGS

Windham, Maine, United States

brbrFOR 2026 RENTING FRIDAY TO FRIDAY ONLYbrSALE LAST WEEK AUGUSTbrbr Come stay at our beautiful Lakeview Lodge. We have enjoyed this home for 30+ years and it is time to share this beauty with others.br Enjoy spectacular views , beautiful sunsets, fires on the beach, clean swimming area, quiet location, all located within 5 minutes to Windham. brThe main home( unit 1) is a 3 bedroom / 2 bath immaculately clean updated house is directly on the lake with views of the White Mountains and breathtaking sunsets across Jordan Bay. brThe main home (6 person *) has an open concept living / dining and kitchen area all with open water views through the large picture windows and sliders to the deck: equipped with A/C for those hot summer days. Well equipped kitchen has everything you will need including a dishwasher. Tile/wood floors throughout. Two bedrooms have king-sized beds and one bedroom has twin beds. All the bedrooms have A/C units. One bathroom has a shower and a tub that is great for bathing toddlers and one bathroom has a custom tile shower.. A gas grill and patio set is provided on the deck overlooking the lake. brUnit 2( 2-3 person) is a smaller one bedroom/1 bath with shower and a combo living/dining area with a double sleep sofa. The sliding doors in the living room open to the shared deck over looking the lake.brUnit 3 (3 person) is a ground level one bedroom with a queen bed, one bath, living room with queen sleep sofa and a kitchen breakfast nook combined. Bath has a shower. This unit open right onto your private beach.brCable and wireless hi-speed internet connection included. brThere is a fire pit and picnic table on the beach for outdoor meals and late night gatherings. brBoat dock, mooring w/ dingy, canoe, small paddle boat and 2 Kayaks provided for your enjoyment as well as lawn chairs for the beach, floating tubes and a stationary float to swim to.br*There is an upcharge of $100.00 per person for occupancy over 12 persons*br* Linens can be provided for a charge of $450.00 *brFRIDAY TO FRIDAY.brMooring is available with the use of a dingy.
Bed 5

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Bath 3

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Sleep 12

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Exceptional(1)

$437.09

/ Nightly
Apartment

Lakefront ADU | Private Access | Projector Theater

Windham, Maine, United States

Summary:brbrTucked along the shores of Highland Lake, this thoughtfully designed ADU offers a peaceful lakefront escape with a cozy projector setup for movie nights in. Enjoy coffee by the water, cook in a full kitchen, and unwind in a quiet space just 25 minutes from Portland.brbrbrbrThe Space:brbrKey Amenitiesbrbr• Private shoreline on Highland Lakebrbr• Ceiling-mounted projectorbrbr• Sleeps 4 brbr• Full kitchen with stove, dishwasher, & fridgebrbr• Coffee maker + coffee + wine glassesbrbr• In-unit washer & dryerbrbr• Room-darkening shades + extra beddingbrbr• Air conditioning & heatbrbr• Wi-Fi + sound systembrbr• Free parking on-site + private entrancebrbr• Security features + smoke & CO detectorsbrbrbrbrThe SpacebrbrbrbrLiving Areabrbr• Ceiling-mounted projector – Big-screen setup for streaming with sound systembrbr• Dining table – Seats two comfortably for meals or workbrbr• Climate control – Air conditioning and heating ensure comfort in any seasonbrbr• Wi-Fi – Fast and reliable connection for streaming or remote workbrbrbrbrKitchenbrbrbrbr• Full kitchen – Includes stove, oven, dishwasher, and refrigeratorbrbr• Cooking basics – Pots, pans, oil, salt, and pepper providedbrbr• Dishes & glassware – Includes bowls, plates, cups, wine glasses, and chopsticksbrbr• Coffee station – Coffee maker and complimentary coffeebrbrbrbrBedroombrbrbrbr• Queen bed – Comfortable mattress with fresh linens and pillowsbrbr• Room-darkening shades – Sleep-in friendlybrbr• Extra pillows and blankets – For added comfortbrbr• Clothing storage – Closet or drawers for longer staysbrbrbrbrBathroombrbrbrbr• Hot water – Reliable and consistent for showersbrbr• Essentials provided – Shampoo, conditioner, body soap, towelsbrbrbrbrLaundrybrbrbrbr• In-unit washer and dryer – Ideal for longer stays or active days on the lakebrbrbrbrOutdoorsbrbrbrbr• Lake front – Steps from the door to Highland Lakebrbr• Free on-site parking – Dedicated space near entrancebrbr• Separate entrance – Full privacy from main homebrbrbrbrOther Things to Note:brbrAdditional Note: For reservations of 29 nights or longer, a security deposit will be required. This is a standard policy for extended stays and helps cover any potential damages or excessive wear and tear. The deposit will be collected prior to check-in and is fully refundable after your stay, provided the property is left in good condition. We appreciate your understanding and cooperation, and we look forward to hosting you.brbrbrbrSecurity Deposit: $550
Bath 1

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Sleep 4

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$819.84

/ Nightly
Private Vacation Home

Sebago Basin Getaway - An Unforgettable Experience

Windham, Maine, United States

Summary:brbrEscape to this expansive Windham home nestled in the Sebago Lake Basin. The home boasts a private sandy beach, direct lake access, shared dock and boat mooring, making it an excellent choice for large groups. Spend your days enjoying water sports on the calm waters of the Basin, then unwind in the evening around the fire pit, while enjoying views of the lake at sunset. Conveniently located near a variety of dining options and entertainment venues, this property promises an unforgettable getaway.brbrbrbrThe Space:brbrNeighborhood and Attractions:brbrbrbrExplore the beauty of Sebago Lake, Maine's deepest and second-largest lake, offering a wealth of recreational activities year-round. While the warm summers bring the enjoyment of watersports, hiking or golf to name a few, the winters bring snowmobiling and ice fishing as well as downhill and x-country skiing. The town of Windham, which is minutes away, offers any and all resources to make your visit enjoyable with many shopping and dining options. Further exploration of the area reveals additional points of interest, such as local artisan shops and seasonal events that enhance the community's appeal. The region also boasts a rich history, with historical sites and landmarks that offer insights into the area's heritage. The availability of local produce and farmers' markets adds to the charm, providing fresh, seasonal goods. Whether enjoying the outdoors, exploring nearby nature, or strolling on the beach, this neighborhood offers the perfect balance of tranquility, recreation, local convenience and appeal. brbrbrbr⭐️ Richardson's Marina/Boat Rentals (0.9 miles)brbr⭐️ Deck House Tavern/Seacoast Adventures (1.1 miles) brbr⭐️ Donnabeth Lippman Park/Chaffin Pond (1.3 miles)brbr⭐️ Tassel Top Park/Beach (3.7 miles)brbr⭐️ Dundee Park/Presumpscot River (5.4 miles)brbr⭐️ East Windham Conservation Area (6.0 miles)brbr⭐️ Lowell Nature Preserve Trailhead (6.7 miles)brbr⭐️ Maine Wildlife Park (8.7 miles)brbr⭐️ Point Sebago Golf Course (10.3 miles)brbr⭐️ Frye Island/Frye Island Ferry/Frye Island Golf Course (11.7 miles)brbr⭐️ Sebago Lake State Park (12.2 miles)brbr⭐️ Naples Causeway/Long Lake (14.3 miles)brbr⭐️ Old Port/Portland, Maine (19.1 miles)brbr⭐️ Pleasant Mountain Ski Area (28.4 miles)brbrbrbrOther Things to Note:brbr• Maximum number of pets is 2. Pet fee will be applied. brbr• Only park in the designated areas. brbr• No extra guests are allowed unless permitted by the owner. brbr• No parties, events and smoking inside allowed. brbr• The guest must comply with the rules under the guest rental agreement.brbr• The guest booking the property must be at least 21 years of age when they book and stay with us. This policy is in place to ensure the safety and comfort of all guests, as well as to comply with local laws and regulations.brbr• The booking price includes a property damage protection fee to cover up to $3,000 of coverage for accidental contents damage and accidental property damage. Property damage protection is included for any damages, subject to exclusions and limitations, that occur to the premises during your rental period. Any damage or accident that is not covered under the policy will be the responsibility of the guest. Damage amounts in excess of the damage insurance will be charged to the guest.brbr• All primary guests must complete the online pre-arrival form/contract via the PMI Vacationland Guest Portal prior to their check-in date. This will help to ensure that all guests have easy access to the property and arrival information needed for a hassle-free check-in process.brbr• PMI Vacationland utilizes a third-party to screen guest identity and check criminal databases to confirm the reservation. Complete terms regarding the guest screening can be provided by the property manager. You may receive an email to complete your screening. Please check your spam inbox for this email and contact the property manager if you have any questions.
Bed 6

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Bath 2

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Sleep 12

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Exceptional(5)

$367.88

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Cabin

Classic Maine Cabin, Private Waterfront Easy Access to Nearby Amenities

Windham, Maine, United States

Take a step back in time and a step forward towards relaxation. Consider this cabin your home away from home while you visit Windham This camp Is on Pettingill Pond in Windham Maine. It has water views, boating, fishing, indoor/outdoor fireplaces, and amazing proximity to amenities for those seeking creature comforts. It has heat and air conditioning to keep you comfortable in hot or cold weather.brIncluded with your stay are three stand-up paddle boards, two fishing rods and fishing accessories, a canoe, and a Kayak. Life jackets and paddles are also provided.brThe spacebrFor those looking for a hotel-type of experience, this is not it! :) It smells like a Maine camp and looks like a camp inside, and out. To me, though, that’s where it shines. You can get a hotel room, just about anywhere, but this Maine camp is just the right place to make memories that can last a lifetime. And if for some reason you want a little bit of civilization after spending some time on the beautiful, quiet, and peaceful Pettingill Pond, you can ride a bike or drive to a large number of attractions just minutes away. Your options for off-pond activities include an Amusement park (Seacoast Adventure), a movie theater where you can eat dinner while enjoying the movie (Smitty’s), a classic drive-in movie theater (Prides Corner), Starbucks, Walmart, Chipotle, and too many other shops and restaurants to list here. For those with Electric vehicles who need EV charging (Tesla, Rivian, Ford, Nissan, etc) - electric charging stations are 3 minutes away (Supercharger and ChargePoint).brbrSo book your stay today and make some wonderful Maine Memories.brbrThings that guests should know:br1) There is a bedroom in the smaller building separate from the main house (the “bunk house). It is a separate structure that’s about 10-15 steps from the main house. The main house has a pull-out couch with a memory foam mattress and an air mattress is available. The main house is the second bedroom. There are no doors in between rooms in the main house (the bathroom does have its own door.)br2) While there is a tub in the bathroom in the main house, the only water heater in the main house is not large enough to make use of the tub.br3) The water heaters on the property are small and intended for quick showers. You won’t be able to take a long, hot shower in there.br4) There is a laundromat (Pratt Abbot) less than 4 minutes away that takes credit / debit cards and cash and can be used via mobile app. There is no washer / dryer on site, but there is a laundromat less than a mile away.brGuest accessbrGuests may access the main house, the dock area, and the bunkhouse at their convenience.brOther things to notebrThings that guests should know:br1) There is a bedroom in the smaller building separate from the main house (the “bunk house). It is a separate structure that’s about 10-15 steps from the main house. The main house has a pull-out couch with a memory foam mattress and an air mattress available. The main house is the second bedroom. There are no doors in between rooms in the main house (the bathroom does have its own door.)br2) While there is a tub in the bathroom in the main house, the only water heater in the main house is not large enough to make use of the tub.br3) The water heaters on the property are small and intended for quick showers. You won’t be able to take a long, hot shower in there.br4) There is a laundromat (Pratt Abbot) less than 5 minutes away that takes credit / debit cards and cash and can be used via mobile app. There is no washer / dryer on site.br You'll have access to WiFi, a hair dryer, AC, an iron, coin laundry, and heating. Kickback, relax, and enjoy everything Windham and our cabin has to offer.br
Bed 2

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Bath 1

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Sleep 6

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