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

Home in Lyme

4.97 out of 5 average rating, 189 reviews

“The Answer” Tidal River-Kayaks Fire pit Fireplace

“The Answer” is listed amongst the 15 best Airbnbs in Ct, from Travellers Worldwide 2022 and 2023 and featured in “Only In Your State” titled “This Riverfront House Will Be Your New Favorite” February 2024 Kayaks included This unique glass-front, tidal river retreat, is privately nestled on historic Hamburg Cove. It offers gorgeous year-round, tranquil water and valley views. Extraordinarily and serene. The interior is open/spacious and bathed in light. Wake up to the many sounds of nature.

May 9 – 16

ﺩ.ﺇ1,058 per night

Guest favorite

Cottage in Guilford

4.96 out of 5 average rating, 158 reviews

Luxury cottage by the sea with hot tub and pool

We built this guest cottage to provide an ultimate luxury experience for people wanting to escape from hectic life!With incredible coastal views, this home is a haven of tranquility. It sits on a special stretch of the Connecticut coast, with spectacular bird and wild life-watching year-round. Enjoy great shopping in Guilford's boutiques around the historic town green. Watch the sun set over the water and relax in the hottub for some night time star gazing year round (pool open June-beg/mid Oct)

Jan 4 – 11

ﺩ.ﺇ1,230 per night

Guest favorite

Apartment in Milford

4.97 out of 5 average rating, 512 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!

Oct 15 – 22

ﺩ.ﺇ738 per night

Guest favorite

Tiny home in Norwich

4.99 out of 5 average rating, 514 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.

Jan 23 – 30

ﺩ.ﺇ568 per night

Guest favorite

Home in Chester

4.98 out of 5 average rating, 196 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.

Jan 22 – 29

ﺩ.ﺇ1,258 per night

Guest favorite

Home in East Lyme

4.96 out of 5 average rating, 164 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.

Jan 14 – 21

ﺩ.ﺇ1,583 per night

Guest favorite

Home in Preston

5.0 out of 5 average rating, 121 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.

Mar 6 – 13

ﺩ.ﺇ1,536 per night

Guest favorite

Tiny home in Smithfield

4.97 out of 5 average rating, 596 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.

Dec 4 – 11

ﺩ.ﺇ572 per night

Guest favorite

Cottage in Chester

4.98 out of 5 average rating, 229 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.

Apr 5 – 12

ﺩ.ﺇ780 per night

Guest favorite

Apartment in East Lyme

4.97 out of 5 average rating, 169 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.

Aug 22 – 29

ﺩ.ﺇ1,582 per night

Guest favorite

Home in Preston

4.96 out of 5 average rating, 600 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!

Oct 23 – 30

ﺩ.ﺇ675 per night

Guest favorite

Farm stay in Hopkinton

4.98 out of 5 average rating, 192 reviews

Farm with a few goats on a lake close to beaches.

This is a bright walk out apartment in our home with a private entrance. We will be here but we give you all the privacy that you want. I have recently lost 3 goats. I still have two goats. This is a rural town 7 miles from Westerly, Rhode Island, and about 12 miles from Mystic. Please read the whole description of this property to make sure it is suitable for your family. Please read my reviews. I think my guests describe the accommodation even better than I do!

Apr 24 – May 1

ﺩ.ﺇ588 per night