Waterfront holiday 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 favourite

Flat in Milford

4.97 out of 5 average rating, 517 reviews

Water front studio apartment with fireplace.

This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

Guest favourite

Cottage in Westbrook

4.85 out of 5 average rating, 99 reviews

Peaceful Riverfront Cottage w/Dock, Walk to Beach

This lovely Cottage sits directly on the Patchogue River with scenic views of the river and marshlands from every room and just a 1/4 mile walk or bike to the Beach. Private, but close to so much, it’s Perfect for a Romantic Getaway, or a long Vacation. Outside, you can enjoy the breeze from the Riverfront Deck, Sun Bathe, Crab or Fish on the Lower Dock, watch the Eagles fly by, or wander about the wooded property. Bring or rent a Kayak and paddle down the river right to the Long Island Sound.

Guest favourite

Tiny home in Norwich

4.99 out of 5 average rating, 520 reviews

Water Forest Retreat-Hikers Haven

Water Forest Retreat Hiker's Haven is a very private semi off grid electrified and heated tiny house just steps away from a brook nestled on 56 acres of lush forest. Enjoy the water views inside from the many windows or out on the deck or firepit area. There are 2 1/2 miles of hiking trails with a pond, marsh and small waterfall. Come here to hike, fish, decompress and rejuvenate in this magical woodland! We also have an Octagon and Treehouse. Please click on our profile picture to read more.

Guest favourite

Home in Chester

4.98 out of 5 average rating, 198 reviews

Stunning Artisan Waterfall Escape, Walk Downtown

Rated one of the top 70 airbnb's near NYC on the online mag "Curbed". Featured on EarthxTV "House of What" series. Over 10 years of craftsmanship went into creating a work of art using more than 80% recycled materials. Known locally as "The Recycle House," this is the perfect place to stay to explore shops and galleries in downtown Chester - just steps away. When you are done shopping, come back and relax in the zen-like garden overlooking a waterfall or curl up inside by the fire place.

Guest favourite

Home in East Haddam

4.95 out of 5 average rating, 103 reviews

Romantic Getaway at The Lake!

Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located, 30 minutes from Hartford, 30 minutes from the Mohegan Casino.

Guest favourite

Home in East Lyme

4.96 out of 5 average rating, 167 reviews

Beachfront Paradise

Beautiful beachfront home available weekly in season (6/22/24-9/2/24) and nightly (2 night min.) off season. Step out the door and into the sand. Sit on the porch and watch sailboat races from Niantic Bay Yacht Club just steps away. Close to downtown Niantic with restaurants, shops, movie theatre, etc. 18 miles from Mohegan Sun Casino. Attractions within 1/2 hour: Beautiful Mystic, CT, several vineyards, Harkness State Park, Eugene O'Neill Theatre, U.S. Coast Guard Academy, golf courses.

Guest favourite

Home in Preston

5.0 out of 5 average rating, 123 reviews

New Lake Front Home w/ Game Room & Stunning Views

Relax and enjoy the breathtaking views of this new contemporary lake front home. Offering the best of New England, 7 min. from Foxwoods, 15 min. from Mohegan Sun, with multiple choices of hiking, boating, shopping and dining. Stunning 14' cathedral ceilings, fully equipped kitchen w/ granite counter tops, tiled shower w/ full amenities and a full game room. You can not get any closer to the water! This 1 Bdrm, w/ open low ceiling loft, sleeps 6, 1100 square ft. building completed in 2022.

Guest favourite

Tiny home in Smithfield

4.97 out of 5 average rating, 602 reviews

Tiny Home Eco-Cottage w/ Lake View + Pet Friendly

Good things definitely come in pet friendly, environmentally conscious, small packages. Solar upgrade makes this lake front cottage 100% energy efficient. Built with an open, thoughtful design offering private bath, washer/dryer, full kitchen, Hotel Suite Luxury bedding and Tempur-Pedic mattress, blazing fast wifi, 46"HDTV (w/ Netflix, Sling, Prime and Plex), private deck with nice lake view. Cozy, charming and stocked with everything you could want for a perfect vacation or staycation.

Guest favourite

Cottage in Chester

4.98 out of 5 average rating, 231 reviews

Updated cottage "Beriozka" on Cedar Lake

Originally from Russia (hence the name “Beriozka” meaning Birch Tree) I live in Stamford CT. About 7-8 years ago I’ve discovered Chester/ Essex area and fell in love. I’ve been coming here during summer to enjoy river rides, during winter just to see snow on the ground of old towns and needless to say during fall – when all the beauty of nature unfolds. Then came an idea to have an own place here and when an opportunity came to buy this small cottage on Cedar Lake I’ve jumped on it.

Guest favourite

Guest house in Cranston

4.92 out of 5 average rating, 305 reviews

Waterfront Studio, 10 min to Downtown Providence

Enjoy your own waterfront retreat in this beautifully renovated, professionally cleaned boathouse down a private drive in a quiet, former estate. This hideaway is just 10 minutes to downtown Providence and the colleges and a short, 10-minute picturesque walk to historic Pawtuxet Village for shopping and dining. Enjoy the private deck, full kitchen, king size bed, washer, dryer, and plenty of space for relaxing or working. Note: This space is not suitable for children or infants.

Guest favourite

Flat in East Lyme

4.97 out of 5 average rating, 175 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.

Guest favourite

Home in Preston

4.96 out of 5 average rating, 610 reviews

Entire House Magical Waterfront Getaway

4 MINUTES TO MOHEGAN SUN! Yet quiet and secluded! Waterfront home! Come relax in this well appointed home with breathtaking view of the Poquetanuck Bay! Enjoying the absolutely gorgeous view from the balcony or porch! Or simply relax, sit around, enjoy each other’s company! Smart TV grants you easy access to thousands of streaming apps! 25 minutes to Ocean Beach, Mystic seaport, Mystic aquariums, Submarine and Library Museum in Groton! 15 minutes away from Foxwood casino!