Waterfront vacation rentals in Old Saybrook

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Old Saybrook

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Tiny home in South Kingstown

4.94 out of 5 average rating, 99 reviews

Waterfront Tiny House in Matunuck

Waterfront tiny house with dock access to the clearest salt pond in the state only 15 steps from the front door. Bring or locally rent kayaks or paddle boards to explore the pond, walk to one of the best beaches in RI, and pop next door to one of America's top rated oyster bars (rated #17 by Food & Wine) for a dinner with a view. Wind down with the sunset or keep the fun going with lawn or board games before snuggling up with a movie before bed. Come stay at the best kept secret in Rhode Island.

Superhost

Condo in North Fork

4.84 out of 5 average rating, 129 reviews

Seaside Summer Escape: 2BR Waterfront Condo w/Pool

Overlooking the Long Island Sound, this oceanfront condo is the ultimate escape. Bask in the sun on a private beach or unwind on the waterfront deck with breathtaking views Minutes from the town center, you’ll find local farms, award-winning wineries, gourmet restaurants & charming shops ⚓️ Explore Greenport: A historic seaport with coastal charm & rich culture 🏖 Premium Amenities – Waterfront deck, private balcony, grills, pool, private beach & parking ⛴ Ferry Access to Shelter Island & CT

Guest favorite

Home in Morris

4.87 out of 5 average rating, 149 reviews

Bantam Lake Waterfront Retreat with Private Beach

Waterfront home on Bantam Lake, 3BR/2BA. Relax on the deck, enjoy the sunrise, swim at your private beach. Kayaks available for use (4); bring your boat or jet ski. Minutes away from hiking, snow skiing, vineyards, biking, and so much more. The area offers great restaurants and family friendly activities that are minutes away. BBQ on the gas grill, enjoy the fire pit on the beach. House is great for couples, individuals & families. Please check first if you plan to bring a boat. 7 maximum.

Guest favorite

Apartment in East Lyme

4.97 out of 5 average rating, 226 reviews

Brand New Direct Lakefront - Panoramic Sunsets

Completely remodeled lakefront apartment offering sweeping views of Pattagansett Lake. Open floor plan, fully equipped kitchen and massive deck make for an ideal gathering place to catch up with family or friends. All three spacious bedrooms offer comfy queen memory foam mattresses, fresh linens and UHD smart TVs. Two full bathrooms, high speed internet and in-unit laundry. Picturesque natural setting yet close to town amenities, restaurants, beaches, casino and area attractions.

Top guest favorite

Home in Branford

5 out of 5 average rating, 14 reviews

Breathtaking Panoramic Waterfront

Relax to sweeping views from every room in this unique, 4600 sq foot direct-waterfront home with two small private beaches, boulders by the water, large pool, hot-tub, outdoor bar, kayaks, and fire pit. 2 floors of wraparound patio/deck, plus 3rd floor loft and roof patio. Open floor plan, sweeping staircase, 5 bedrooms plus loft, 3.5 bath plus half bath and outdoor shower by pool. A real oasis! (Note: pool not heated and open mid-may to mid-Oct only; hot tub closed Jan-March)

Guest favorite

Home in New Fairfield

4.92 out of 5 average rating, 116 reviews

Beautiful Lakefront Retreat with Private Dock

Relax on the lake at this beautiful, one of a kind 3 bedroom, 2.5 bath DIRECT waterfront home in a private community on peaceful Squantz Pond, adjacent to Candlewood Lake. Enjoy spectacular views across the lake of unspoiled Pootatuck State Forest from the deck or screened in porch. Swim, fish, or just relax on the private dock. Kayak and paddleboard rental nearby. The home is central air-conditioned with a fully equipped kitchen. Our special place is waiting for you!

Superhost

Home in Stonington

4.87 out of 5 average rating, 113 reviews

Waterfront Cottage with Dock

Arts and Crafts cottage on an ocean cove in Stonington with dock and close to the beaches. On same cove as Saltwater Farm Vineyard and nearby to Mystic Aquarium and Seaport, great restaurants, and Foxwoods and Mohegan Sun resorts. You’ll love the backyard and dock. I offer complimentary canoe, kayak and paddle board use so you can enjoy the water. Bring your own boat or rent one for 50% off at Stonington Marina. My place is good for couples, families with kids, and pets.

Guest favorite

Houseboat in North Fork

5 out of 5 average rating, 11 reviews

Peconic River Boatel

Perfectly updated nautical houseboat situated on the scenic Peconic River. Featuring two picturesque bedrooms, a full service eat-in kitchen and a living room with panoramic river view. Enjoy your morning coffee on the outside deck while taking in the sunrise. This historic waterfront town was named to Forbes Advisor’s “Best Places to Travel in 2023” — one of just 11 U.S. destinations on this year’s list. A must see for adventurers and families alike!

Guest favorite

Home in South Kingstown

4.98 out of 5 average rating, 57 reviews

Spectacular Waterfront Home

Beautiful waterfront property with high end furnishings that will provide an unforgettable experience for our guests. Memories will be made here at the custom farmers table, in the cozy living room and in the beautiful outdoor spaces. Waterfront dock and boathouse fully furnished with paddle boards and kayaks in season and fire pit in the fall will insure guests take full advantage of this perfect setting. 20 minutes to Newport.

Top guest favorite

Cottage in Old Saybrook

5 out of 5 average rating, 98 reviews

Cozy Waterfront Retreat

Serene waterfront retreat! Direct waterfront property on Oyster River perfect for kayaking, fishing, paddle boarding or just soaking up the sun. This cozy cottage with views of stunning sunsets allows guests to relax and unwind. Minutes to local restaurants and shopping, walking/bicycling distance to the towns best beaches; close to outlets and casinos. Quaint, charming cottage with beach decor throughout.

Guest favorite

Home in Waterford

4.95 out of 5 average rating, 114 reviews

Coastal New England Waterfront Home-The Reed House

The Reed House – Waterfront Getaway in Waterford, CT Enjoy the best of both relaxation and adventure at The Reed House, located in the peaceful Pleasure Beach neighborhood of Waterford. This charming home offers breathtaking views of Jordan Cove and is just steps away from the beach, making it the ideal retreat for families, friends, or anyone looking to unwind by the water..

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What guests are saying

Waterfront NoFo Cottage w/ public beach access

4.94 out of 5 average rating, 31 reviews4 months ago

Andrew and Kenneth were excellent hosts. Some of the most professional, responsive and attentive I have experienced. The home is cozy, and the space is really well used and appointed. Some of the appliances are a bit quirky -- like the washer/dryer, which isn't very effective; and the stove/oven which the hosts are aware needs some repairs. The location is lovely. Be prepared to listen to the ducks on the lake. They can be loud even during the night. The outdoor shower was the icing on the cake for me. I nearly stayed longer, except I had another opportunity overseas.

Home in North Fork

What guests are saying

Direct Shoreline Long Island Sound Waterfront

4.95 out of 5 average rating, 80 reviews7 months ago

Our visit was utilitarian. We needed accommodations for us, our grown children and grandchildren and a dog. But the site of the cottage, its charm, its comfort made us wish we were staying another week. James' thoughtfulness went beyond any other Airbnb hosts' that we've experienced. Everything we might need if we were staying 10 days was there, clean, labeled. Thank you, James.

Cottage in Guilford

What guests are saying

Breathtaking Lake Williams Lakefront

4.84 out of 5 average rating, 25 reviews8 months ago

Beautiful and easy little cottage, lovely porch with wonderful big swing to nap on with the pup, luscious huge lawn to feel space and privacy, and absolutely beautiful lake view, easy rock step into shallow section to launch our floaties and Wayne’s paddle boards. Easy living with picnic table and great Weber grill, and second small fridge in the boat house. A keeper!

Home in Lebanon

What guests are saying

Salty Breeze - Waterfront Cottage on the Cove

4.95 out of 5 average rating, 73 reviews1 week ago

This was a prime location for any level of activity. The home was in walking distance to the beach. It had a water view with endless majestic shore birds swimming past the outdoor sitting area. The local restaurant choices are endless. Mystic, New London and Groton are just a short car ride away. Harkness park has an expensive shoreline with panoramic views and it takes just a few minutes by car or bike. I would definitely book a stay here again.

Home in Waterford

What guests are saying

One Bedroom Hamptons Waterfront Cottage

5 out of 5 average rating, 20 reviews7 months ago

The cottage was absolute heaven! It’s on a beautiful property with wonderful amenities. There is no shortage of things to do near by, but you could also enjoy a peaceful relaxing stay on property. We swam in the pool, grilled on the deck, played ping pong and took the canoe out on the bay. Sunsets from the cottage were great too. We brought our dog along and the property was very pet friendly. The cottage itself was clean and really had everything you could need. We’ll definitely be back! Brian was lovely to deal with and has set up a hidden gem here.

Guesthouse in Hampton Bays

What guests are saying

Stunning waterfront modern farmhouse with dock.

4.98 out of 5 average rating, 44 reviews4 weeks ago

Returning guest, we had a wonderful weekend at Michelle's idyllic home. Plenty of space for our two families and 3 kids. The kids love having their own space in the "she shed" while the adults enjoy the lakeside views from both the yard and inside the spacious living area. The house is always immaculately clean. Beds and other furnishings are comfortable, and the house is an easy drive to everything the North Fork has to offer. We look forward to returning (again!) soon.

Cottage in North Fork

What guests are saying

Privateers Boathouse (Village Waterfront)

4.82 out of 5 average rating, 28 reviews4 months ago

We always visit Essex once a year and this is out first time that we stayed elsewhere besides a hotel. A perfect place in a perfect location. Loved everything about it and Annie and this is our new Essex retreat for the years to come. Could not be more happy with all aspects of our stay.

Guesthouse in Essex

What guests are saying

Waterfront Cottage - Harbor View Landing - Mystic, CT

5 out of 5 average rating, 58 reviews1 week ago

Oh 100% What a beautiful place! From what I could tell, a developer build a number of small cottages at a point overlooking the water in Groton/Mystic.. Well done. Totally smart plan; the places are gorgeous. The grass is perfect. They’ve got Chesapeake chairs set up around solo stoves. The weather was beautiful. There are stars in the sky. It could not have been better - really amazing The cottage has a Nantucket boating theme to it. It’s clearly very well built. Everything is new. Everything is pristine. Everything is there that you could possibly need Rent this place you’ll be glad you’re did .

Cottage in Mystic

What guests are saying

Waterfront home with dock, kayaks & paddleboard

4.96 out of 5 average rating, 48 reviews5 months ago

Perfect stay! The location was private, beautiful and safe and also close by to Oceanside restaurants. The house was perfect for my husband, toddler and infant with lots of room to run around outside. Waking up every morning to coffee with a sunrise over the pond and the fireplace on was heaven. Thank you for the magic memories!

Home in Charlestown

What guests are saying

Direct Waterfront with Private Beach - Entire Home

4.96 out of 5 average rating, 71 reviews6 months ago

I was in town for a family event and wanted something other than a hotel room. The home was cozy and inviting, instructions were clear and precise. Being late October the weather was unbelievable warm. We (me and 2 sisters) were able to enjoy the wonderful deck and beautiful scenery. It was peaceful and quiet with an amazing views. Thank you Larry and Denise for sharing your beautiful home.

Home in Harwinton

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