Home Vacation Rentals By Owner In Old Saybrook, CT

Showing 20 Of 84 Vacation Rentals
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Exceptional(7)

$494.5

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Private Vacation Home

Tranquil property, amazing sunsets!

Old Saybrook, Connecticut, United States

New Outdoor Shower! brbrRemodeled 3 bedroom, 1.5 bath beach home nestled in Old Saybrook, CT. Sits on a private 1/2 acre. Just step outside and sit on the patio and listen as birds fill the air with the most tranquil sounds. Tons of wildlife. On any given day you may see all kinds of birds, chipmunks, squirrels, rabbits, deer, wild turkeys. An eagle soaring overhead or egrets playing in the marsh. Sunsets can be seen from the house and backyard. Always a beautiful end to the day. brbrThe house features a master bedroom with a queen bed and 1/2 bath. Another queen bedroom with a small desk, chair and printer. The third bedroom has two twin beds and two additional bean bag chairs for relaxing. There is one full bathroom with tub. Central air and WiFi provided.brbrThe outdoor space is very private with a gas grill and table for six. There is also an outdoor fire pit with six adult Adirondack chairs and 3 kids, for those nights you are craving a s’more! brbrThe property is a short bike ride to Cornfield Point beach (about a 1/2 mile) or just minutes away by car to Harvey's beach. The Cornfield Point community is golf cart friendly. Golf carts can be rented from Hawkes Golf Vehicles in Clinton, CT. They do deliver/pick up the vehicle. brbrThe area is great for walking or running. Take a trip down Maple Avenue towards Fenwick and you will not be disappointed with the views. Lighthouses can be seen in the distance along this path.brbrBeach chairs, towels, toys, umbrella, beach cart and bikes provided. Nothing to do but pack your bags!brbr(Full disclosure: Exterior cameras for security purposes. Owner has a cat at house on occasion.)brbrOld Saybrook is a quaint town with lots of restaurants, shops, and beaches. It’s a great location for families, couples or a girls trip. If you are looking to retreat to a peaceful location with the most magnificent views, this is the place to be!brbrGreat place to stay if you are attending a wedding at the Saybrook Point Resort and Marina. About a 6 minute drive.
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Exceptional(2)

$521.49

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Private Vacation Home

Fenwood Coastal Getaway Private Beach Access

Old Saybrook, Connecticut, United States

Summary:brWelcome to your perfect beach getaway! This charming beach house offers everything you need for a relaxing and comfortable stay. The home comfortably sleeps 6 with 3 bedrooms, 2.5 bathrooms. You’re just a short stroll away from the Old Saybrook private Fenwood beach, where you can soak up the sun, swim, or simply relax and listen to the soothing sound of the waves.brbrThe Space:brPrior to your arrival, our home undergoes professional cleaning to ensure a clean and welcoming environment. We meticulously prepare and set up each space, paying close attention to detail, so that you can immediately relax and enjoy your stay from the moment you step through the door.brbrWith three bedrooms, there's plenty of space for the whole family or a group of friends to unwind after a day of sun and sand. All 3 bedrooms are located on the upper level. A full bathroom with a detachable shower head is also on the upper level. Bedrooms 1 and 2 feature queen beds. Bedroom 3 boasts a king bed, tv and a private bathroom with a shower.brbrOur kitchen is equipped to cater to your needs. It features a dishwasher, refrigerator, and stove, ensuring convenience at every turn. We have stocked the kitchen with an array of essential cookware, serving utensils, basic paper products and cleaning supplies for hassle-free dining and upkeep. For coffee enthusiasts, we provide both a drip coffee maker and a Keurig machine, inviting you to bring your favorite coffee blends for a personalized brew. Additionally, the kitchen includes a microwave, rice cooker, toaster and an air fryer enhancing your meal preparation options. A gas grill is also available for guests to use.brbrThe living area is designed for comfort and relaxation. It features an L shaped LoveSac couch, perfect for unwinding or socializing. For entertainment, enjoy our large HDTV with ROKU that allows you to easily log into your apps.brbrAfter a day of beachside fun or exploring the town, head to the lower level where entertainment awaits. Sink into the seating area to watch your favorite shows or movies on the TV or gather around the table for a friendly game of cards or board games. This versatile space is perfect for unwinding, bonding,brand creating lasting memories. A half bathroom is also located in this lower area.brbrAnd don't worry about packing too much - a washer and dryer are conveniently located on-site for guest use, allowing you to keep your beachwear fresh and ready for another day of coastal adventures. Basic laundry supplies are available for your use.brbrWe ensure every bathroom is well-stocked for your convenience, providing an array of guest towels along with high-quality shampoo, conditioner, and body wash. Additionally, essential paper products are readily available. For your grooming needs, a hair dryer is provided, ensuring you have everything you need for a comfortable and hassle-free stay.brbrGuest Access:brYou will have access via smart lock to the home
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Exceptional(20)

$166.2

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Private Vacation Home

Beach house available May 1-31, 2026

Old Saybrook, Connecticut, United States

This cozy Knollwood Beach home has 3 bedroom, plus a LR open up couches that sleep 2 in the family room, 2 full baths - is available for rental (INQUIRE w/email for discounted month or longer rentals).It was completely remodeled 7 years ago and is equipped with a full kitchen and modern appliances. It is a short distance from Fenwick Golf Course and there is a golf cart to use in the area and at the golf course during your stay. It includes AC, W/D, dishwasher, patio, gas grill, exterior wood fire pit, & parking for 4 cars. Neighborhood also has a park which includes a basketball court, tennis court, playground, and baseball field. There is also a town small boat launching area a short distance from the house for kayaks and small boats on the South Cove of the CT River with access to LI Sound. This home is excellent for beach stays and stays involving events at the Saybrook Point Inn, Water's Edge Resort, and the Elks Lodge in Westbrook, CT. It is also within 30 minutes of Yale U, Wesleyan U, the Coast Guard Academy, and Connecticut College. The Katherine Hepburn Cultural Arts center and Fenwick Golf Course are a short distance from the property; it hosts wonderful concerts and programs. There are several local attractions including a seasonal Old Saybrook Mini Golf Course, Essex Steam Train, the Griswold Inn, CT River Museum in Essex, Shopping Malls Westbrook, Clinton, and Waterford. The scenery in the are is spectacular!
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$195.2

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Cottage

Saybrook Point Cottage - Charming and Private

Old Saybrook, Connecticut, United States

Charming, one bedroom cottage is located on historic Saybrook Point where the Connecticut River meets Long Island Sound. This fully furnished, very comfortable house with rustic yet refined decor features one bedroom, one bath, living room, and a fully-equipped eat-in kitchen. It also has SmartTV, Wifi, and air conditioning. We provide linens and towels for you!brbrAt the Saybrook Point Cottage, we are the business of hospitality. In addition to our strict housekeeping protocols, we also offer Contactless Check In/Check Out. Rest assured that we are doing everything, and then some, to ensure the health and safety of all our guests and to make your stay as comfortable and enjoyable as possible!brbrSituated on a quiet street that ends at Saybrook's South Cove, there are sliding glass doors that open onto a beautifully landscaped, private park-like lawn. There is no swimming in South Cove, so it's just a five minute drive to the sandy Town Beach. The bright and airy guest house is ideal for singles or couples looking for relaxation and adventures. brbrMAXIMUM OCCUPANCY: TWO PERSONS.brbrPET FRIENDLY- Bring your pets!! Please note the property is not fenced in.brbrSometimes you need a quick change of scenery to break the cycle! brbrLocated less than a two hour drive from mid-town Manhattan and Boston, there is also an Amtrak stop in town.brWalk to the water or into the village. brEnjoy the views from the deck or barbeque with the gas grill. brThe area is perfect for long walks, bicycling, scenic drives, canoeing, kayaking, antiquing, and more. brbr30 minutes to Mohegan Sun and Foxwoods br20 minutes to Mystic Seaport and Aquarium br15 minutes to the Goodspeed Opera House and Outlet Malls brOne-quarter mile to the Saybrook Point Spa and Fitness CenterbrbrAvailable year round. See summer rates below. br2night minimum off- season. brSaturday-Saturday minimum from Memorial Day-Labor DaybrLonger stays are negotiable. Contact owner for additional information and photos.brbrFeel free to contact owner with any questions .brbrKeywords: House, Cottage, Getaway, Bungalow, Love Shack, Weekend Retreat
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Exceptional(76)

$490.39

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Cottage

Wonderful location, walk to beach, private yard, credit cards

Old Saybrook, Connecticut, United States

The Cottage was chosen as one of the top ten unique places to stay in Ct.br'Awesome Cottage! Great Owner!brAbsolutely loved this house and will definitely plan on staying here again! My husband is originally from Connecticut and his entire family still lives there. Traditionally we stay with family when we visit but I decided to rent a house this trip so we could entertain and have everyone over. This house was charming and very comfortable. It was my mother in laws 80th birthday and I had about 25 family members over for a dinner party. Every person who entered the house commented on what a terrific cottage it was. Having the upstairs loft was a perfect space for my son to have his privacy and a place to relax. He (and I) loved having the wireless internet connection that worked great! The outdoor area was very private and the deck was a wonderful space to hang out and kick back. Everyone really enjoyed the art work throughout the house and commented that it provided warmth and character to the cottage. Lastly I want to share my comments on the owner Yvette, she was very prompt in her responses to me and a real pleasure to work with through the rental process. Yvette thank you so much for sharing your beautiful home with us, it was the most memorable visit to Connecticut that our family has ever had. Take care, my best, Julianna (This was the first time I ever rented a home online or used the Home Away site, it was a great experience!)'br br brResponse brbrI have been renting my cottage since 2006. I own the lot next door, a tiny wooded lot, so the back yard is very private. The house is on a private dirt home has a large deck, front porch, fireplace, I provide linens, spices, paper towels, trash bags.brbrThis is the home I raised my boys in. It was always filled with love....br-----------------------------------brHome Away site, it was a great experience!)brbrOur Beach house is tucked away in a quiet private Connecticut shoreline neighborhood. Bike or flip-flop to our private beach and fishing pier. Our Cottage boasts a large, private, yard that affords lively games of horseshoes or croquet. Nap or read in a hammock or relax with a cold refreshment under the gigantic trees. Back deck offers a picnic table and grill for hotdogs, hamburgers or lobster.brbrCottage Amenities - Fresh and Vibrant Decor, books to read, sea treasures, fresh linens, coffee maker, teapot, dishes. Your flip-flops are a must!brbrThe Old Saybrook Town beach is Amazing and within biking distance. The 'Kate' offers sophisticated entertainment. Penny Lane Pub is a lively Irish watering hole and Dock and Dine is situated on the waterfront for sea-fare dining. Stroll downtown and browse the plethora of Antique Stores and Seaside Treasure Shops where Katherine Hepburn was often spotted. Wander over the causeway and down RT.1 and keep exploring the Connecticut Shore!brbrOffering three homes on the Connecticut shoreline as vacation rental properties in Old Saybrook and Guilford for the past seven years, we take great pride in caring for our guests as well as in accommodating and tending to their needs and comfort. Our homes are designed with local art and treasures and reflect our love and passion for decoration, beauty and the creation of aesthetic surroundings which welcome and embrace you. Our goal is to provide a setting where you, your family and your friends can enjoy, relax and create memories that will last a lifetime. Our reviews testify to this and consistently reveal the happiness and joy our guests have experienced while staying at our properties. Come stay with us and see for yourself what our homes are all about.brbr__________________brbrbrThe area...brExperience New England’s shoreline year round at one of Old Saybrook’s most desirable and family friendly areas. Spend the day basking in the sun at the Saybrook Manor Association private beach club, have your children playing at the club's playground, enjoy all sort of social events, or go for a change to one of the 2 beaches just a five-minutes walk away.brbrNeed a break from the beach Stop to dine at some fine restaurants nearby. Travel just a little further and visit Mystic Aquarium, Mystic Seaport, take a ride with your kids across the countryside, see Beautiful New England the old-fashioned way on the Essex Historic steam train, enjoy a cruise on the Connecticut River or enjoy an evening at the Mohegan Casino. Peddle along the ocean side at sunset, head to the shops along Main Street or take a ten-minute drive to the shopping large outlets in Westbrook and Clinton.brbr
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Exceptional(136)

$423.92

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Private Vacation Home

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Old Saybrook, Connecticut, United States

Gather your people at our 1795 historic homestead near Coastal Connecticut, ideal for reunions, retreats & wedding weekends. Cook & linger in the well-stocked kitchen, read fireside or spread out across the private lawn and porches. A character-rich, memory-making home!brbr⭐ “Full of character, spacious and comfortable—our family loves coming back.” – Stephenbrbr🏜 HIGHLIGHTSbr✓ Authentic 1795 historic estatebr✓ Private grounds, porches, firepitbr✓ Well-stocked kitchen & cozy fireside spacesbrbrTHE SPACEbrbr***Message us for weddings or other large events!***brbrHistoric charm with private grounds, fireside rooms, porches, and a cook-ready kitchen.brbr🏷 Main FloorbrbrKitchen & Dining Room br∙ FULLY stocked kitchen w/plenty of counterspace for at-home baking and cookingbr coffee maker, tea kettle, blender and toasterbr∙ Cooking oils and seasoning essentials br∙ Abundance of dishware, glassware and silverware, including children’sbr∙ Full-sized fridge and freezerbr∙ Gas stove and ovenbr∙ Microwavebr∙ Dishwasherbr∙ Blenderbr∙ Slow cookerbr∙ Dining room table, seating for 4brbrLiving Room br∙ Smart TVbr∙ Netflix, Prime Video, Disney Plus, Hulu, HBO and morebr∙ Sound systembr∙ Fireplacebr∙ Board gamesbr∙ Booksbr∙ ToysbrbrBedroom #1 (Primary Bedroom)br∙ King size bedbr∙ Premium mattress and comforterbr∙ Bedside table and lampbr∙ Large closet w/ hangersbr∙ Booksbr∙ MirrorbrbrBedroom #2br∙ Queen size bedbr∙ Premium mattress and comforterbr∙ Room darkening shadesbr∙ Bedside table and lampbr∙ Large closet w/ hangersbrbrBedroom #3br∙ 2 Double bedsbr∙ Premium mattress and comforterbr∙ Room darkening shadesbr∙ Bedside table and lampbr∙ Large closet w/ hangersbr∙ BooksbrbrBathroom #1 and Laundry Roombr∙ GE high-efficiency washer/dryerbr∙ Tide Free and Gentlebr∙ Showerbr∙ Single vanity and mirrorbr∙ Shampoo, conditioner and body soapbr∙ Makeup washclothbrbrBathroom #2br∙ Showerbr∙ Bathtubbr∙ Single vanity and mirrorbr∙ Shampoo, conditioner and body soapbr∙ Makeup washclothbrbr🏷 2nd FloorbrbrBedroom #4br∙ Double bedbr∙ Single bedbr∙ Premium mattress and comforterbr∙ Room darkening shadesbr∙ Bedside table and lampbr∙ Large closet w/ hangersbrbrBedroom #5br∙ Queen size bedbr∙ 2 Single bedsbr∙ Premium mattress and comforterbr∙ Room darkening shadesbr∙ Bedside table and lampbr∙ Large closet w/ hangersbr∙ Ceiling fanbr∙ Full-length mirrorbrbrHallwaybr∙ Office table and chairbrbr🏷 Outdoor Space(s)brbrSunroom br∙ Large glass roof for natural sunlightbr∙ Comfortable sofabr∙ Rocking chairbrbrBackyardbr∙ Firepitbr∙ Outdoor seatingbr∙ Play areabr∙ Picnic tables and umbrellabrbrBalconybr∙ Outdoor seatingbr∙ Coffee tablebrbrPorchbr∙ Enclosed porch br∙ Outdoor seatingbrbr🏷 Parkingbrbr∙ Room for 6 vehicles but can hold up to 50+ for large events (contact us for details)brbr🚘 NearbybrbrMain Street Shops & Boutiques (walking ~3 min): Charming local shopping, antiques, galleries and cafés in the heart of Old Saybrook.brAshlawn Farm Coffee (drive ~2 min): Local favorite café with specialty coffee, pastries, sandwiches and outdoor seating.brMonkey Farm (drive ~3 min): Popular bar & grill with classic fare and laid-back vibe.brPaperback Cafe (drive ~3 min): Cozy breakfast/brunch spot with community favorites.brSwell (drive ~3 min): Highly rated acai & healthy café option on Main Street.brJames Pharmacy Bed & Breakfast and Gelateria (drive ~4 min): Historic gelato and coffee stop with old-town charm.brFresh Salt (drive ~5 min): Upscale seafood dining with seasonal and local offerings.brCafe Toscana (drive ~4 min): Casual coffee & tea spot for daytime breaks.brOtter Cove Restaurant & Bar (drive ~7 min): Stylish gastropub with seasonal local menus.brSaybrook South Green & Historic Sites (drive ~5 min): Historic district featuring the Humphrey Pratt Tavern and heritage architecture.brThe Kate – Katharine Hepburn Cultural Arts Center (drive ~4 min): Live theater, arts and tribute exhibits to the legendary actress.brSaybrook Breakwater Light (drive ~6 min): Iconic sparkplug lighthouse and peaceful waterfront setting.brLynde Point Light (drive ~6 min): Historic Long Island Sound lighthouse ideal for photography and scenic views.brOld Saybrook Town Beach (drive ~7 min): Saltwater beach with seasonal swimming and sunbathing.brHarvey’s Beach (drive ~9 min): Popular sandy shore and summer gathering spot on Long Island Sound.brCrystal Lake Town Park (drive ~5 min): Community park with playgrounds, trails and open recreational space.brbrTanger Outlets Westbrook (drive ~7 min): Outlet shopping with over 150 brands for fashion and gifts.brRocky Neck State Park (drive ~15 min): Beach, camping, hiking and nature trails.brHammonasset Beach State Park (drive ~26 min): Connecticut’s largest shoreline park with miles of sandy beach and boardwalk.brEssex Village (drive ~20 min): Historic small town with antique shops, riverfront views and dining (great half-day trip).brbr💡 Other things to notebr✓ This is a true historic home, full of charm and character, which means you may notice older-home quirks that come with a property from the late 1700s.br✓ The home sits near a main road, so you may hear some traffic at times, though the yard and grounds feel private once you’re settled in.br✓ The beach is ~5 minute drive from the property.br✓ Some areas on the property are reserved for caretaking and maintenance use and aren’t accessible to guests.
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Exceptional(49)

$288

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Private Vacation Home

Steps to the Beach, Cozy Year Round Cottage Pet Friendly

Old Saybrook, Connecticut, United States

Updated furnishings, and freshly painted. Full bath with easy to clean flooring and full size washer and dryer. Inviting and cozy, pet friendly beach house in a small private association. Large open living space with fully stocked kitchen, dining room and desk area to work remotely if you need to. Generously sized, fully fenced yard for your fur babies, with a patio and picnic table. Well appointed, with all the comforts of home, and bright open space. Walk 2/10 mile to a private beach. Streaming enabled TV and wifi included. You'll never want to leave!brbrThe PropertybrbrEscape the noise of the city and hide away at this lovely cottage!brbrCOMMUNITY AMENITIES: Easy access to private Saybrook Manor Association beach so swimming, boating, and all kinds of CT shoreline activities are at your fingertips!brbrOUTDOOR LIVING: Patio table and chairs for 6. Folding wagon to take to beach, beach towels.brbrINDOOR LIVING: Smart TV, dining table with seating for 6, breakfast bar with seating for 2 more, full size bathtub, plenty of closet space, iron and full size ironing board. Playing cards, Uno and puzzles.brbrKITCHEN: Fully equipped, microwave, Keurig, drip coffee maker (including complementary coffee and tea), cooking basics, baking sheets/dishes, complimentary spices, dishware/flatware, lobster pot and accessories (shell crackers and shrimp forks).brbrGENERAL: Free WiFi, washer/dryer, bedding linens and towels included, central heating, keyless entry, complimentary toiletries, cleaning essentialsbrbrPARKING: Driveway (4 vehicles)brbrHouse Rules and Policiesbr- No smokingbrbr- Pet friendly - NO MORE THAN TWO PETS allowed at one time. brbr- No events, parties, or large gatheringsbrbrPets welcome with a small fee paid up front.brbrClose to all kinds of activities and shoreline fun.brbrHarvey's Beach 2 milesbrMonkey Farm 1.7 milesbrStarbucks 1.8 milesbrOld Saybrook Town Launch 2.7 milesbrSaybrook Point Marina 3 milesbrMystic Seaport 28 milesbrMystic Aquarium 28 MilesbrClinton Premium Outlets 8 milesbrbr*WE STRONGLY ENCOURAGE YOU TO GET TRIP INSURANCE*brWe have exterior cameras, one at the front and one at the back of the property to protect it during vacancies and weather events.
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Exceptional(5)

$1322.5

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Private Vacation Home

Stunning Ocean view with Hot tub. Sleeps 10

Old Saybrook, Connecticut, United States

Enjoy your morning coffee with a beautiful ocean view! Stunning remodeled 3388 sqft Colonial with sweeping Ocean views in a Private Beach Association with use of waterfront beach. Private courtyard patios with fountain, Ocean view balcony and garage. Outdoor shower with changing rooms. Outdoor fountain & games. Also, access to association amenities... playground, basketball court and tennis.brbrThe home has a basement with a sauna and a movie room. It also has a separate room with a sleeper sofa. The main floor has a full bath and an office with a queen Murphy bed. The upper floor has a King bed with its own full bathroom. 2 other queen bed rooms and a room with two twin beds. Upper floor also has a full bath.brbrHouse has an attached garage with parking for 5 cars in total. *There is golf cart in garage that CANNOT be used. May fit small car in therebrMinimun Stay Required. Please reach out to the owner if you do not see your requested dates available. There may be some schedule flexibility.brbrbr* ** This is not a party house. We hope that you be respectful of our house rules. ***brbrbr**** Please note the followingbr-The home has one Ring doorbell in the courtyard area. The recording device is always on and only records when they sense motion. brThere is also a camera in living room ( that does not video or have audio, it will just takes a picture if there is unexpected motion)
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