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Waterfront vacation rentals in Old Saybrook

Find and book unique waterfront rentals on Airbnb

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Popular amenities for Old Saybrook waterfront rentals

Waterfront apartment rentals

Top guest favorite
Apartment in Northport
4.99 out of 5 average rating, 147 reviews

Amazing one bdrm flat at the beach!

BethRating, 5 stars6 days ago
Jeannette was there to greet us and made sure we knew where everything was and that we had everything we needed. She even provided breakfast. Her place was immaculate. The location was amazing. She made our departure very easy. We are looking forward to staying there again. If you looking for a great place to stay, this is it.
Guest favorite
Apartment in North Kingstown
4.97 out of 5 average rating, 155 reviews

Wickford Waterfront 12 min to Newport & 15 min URI

NiyatiRating, 5 stars6 months ago
Elaine has a lovely apartment. Very pristine and quiet with amazing views. Our stay was extremely comfortable. Her instructions were perfect and we had no problem with whatsoever anything. If you’re ever there do not miss the morning sunrise. Outstanding. Thank you Elaine & Rich for a lovely stay. We hope to come back some day.
Guest favorite
Apartment in Stonington
4.95 out of 5 average rating, 289 reviews

Mystical Ocean View in Historic Stonington Borough

YuwenRating, 5 stars3 weeks ago
Sam's place exceeded our expectations! The view was marvelous, and the house was beautifully decorated with a wonderful collection of books we truly enjoyed. The kitchen was fully equipped with everything we needed, and the room was super clean. We had a great time during our two-day stay. The small town offered so much to explore, and the nearby seafood market was a delightful surprise. we had fresh lobster at a very reasonable price. We highly recommend Sam's place for a relaxing and enjoyable getaway!
Top guest favorite
Apartment in Guilford
4.96 out of 5 average rating, 83 reviews

Cozy Private Lake Q Retreat

JenniferRating, 5 stars2 weeks ago
Great little spot. This rental has everything you need. Forget something-they got it. Very clean and modern with thoughtful touches. Had an extended stay here and extended for longer. 1 bedroom with loft that owner made into another bedroom for me. Loved it. Great deck, stunning lake view from all the windows. Owner very responsive to any needs. 100 percent recommend. Neighborhood lovely and quiet. Amazing respite.
Top guest favorite
Apartment in Stonington
4.97 out of 5 average rating, 216 reviews

Mystic River Getaway - Walk To Downtown & Seaport!

SarahRating, 5 stars5 days ago
We just came home from our long weekend in Mystic and Anthony’s place was a great find. We comfortably fit myself, my husband, and my 2 year old with ample space. The house was walking to distance to many amenities including downtown Mystic which we enjoyed. I would highly recommend Anthony’s place to anyone else traveling to Mystic!
Guest favorite
Apartment in College Hill
4.97 out of 5 average rating, 204 reviews

Jennifer’s Historic Downtown Loft

ChristinaRating, 5 stars3 days ago
Wonderful stay! Very clean, spacious, conveniently located with parking. Thank you!
Guest favorite
Apartment in Middlebury
4.92 out of 5 average rating, 121 reviews

Cozy Apartment with Water View of Brook

EvelindaRating, 5 stars4 days ago
We were recently in town to visit family, staying at Traci’s made our visit enjoyable and relaxing. Check-in was easy, the apartment was clean with a comfortable bed and a peaceful view of the brook. Overall, we had a pleasant stay, thank you Traci!
Top guest favorite
Apartment in Milford
4.98 out of 5 average rating, 104 reviews

The Pond Mill Retreat w/ 2 Bdrms & Pool

JudyRating, 5 stars3 days ago
Dawn and Bob’s place is one of the top Airbnb’s we have stayed in! Top notch in every way. It was spotless, comfortable and had everything we needed. And on top of that Dawn and Bob were the most friendly hosts we have met! I would recommend this Airbnb without reservation and will be back whenever we are back in CT!

Waterfront house rentals

Guest favorite
Home in Milford
4.96 out of 5 average rating, 221 reviews

Designer Beach Retreat on Exclusive Cedar Beach

ChristopherRating, 5 stars2 days ago
We love staying at Cail and Jayne’s beach home in Milford! This is our second time at one of their homes, first time on the marsh side of street. It’s a beautiful setting and great for bird watching! This is also why I love staying at superhost properties. Communication is always fast and easy, the place is spotless, tons of amenities, easy to follow instructions, comfortable beds, and the home is decorated beautifully. My Mom and I were sad to leave. Tl;dr: Great home, great hosts, great location. Highly recommended!
Guest favorite
Home in Coventry
4.98 out of 5 average rating, 110 reviews

Cozy cottage 5 minutes from UConn

TiffaniRating, 5 stars1 week ago
Wonderful and peaceful stay for a relaxing girls weekend. Outstanding clean and comes with everything you may need. The space is kid friendly, and extremely beautiful. Would definitely stay again.
Top guest favorite
Home in Vernon
4.99 out of 5 average rating, 152 reviews

Luxe Bolton Lake

LukeRating, 5 stars6 days ago
Super clean, quiet and comfortable with lots of great touches. We didn’t get the best weather for lake life but the house made up for it nicely. Look forward to staying again someday!
Guest favorite
Home in North Stonington
4.96 out of 5 average rating, 122 reviews

The Perch

DeniceRating, 5 stars7 months ago
I have stayed at lots of places in the last few years . . . and this place ranks right at the top. It is beyond beautiful. The water views from the living room and both bedrooms made it hard to leave and come home. It's actually even more amazing than the pictures. Don't think twice! Book this place now!
Guest favorite
Home in Groton
4.94 out of 5 average rating, 198 reviews

True Ocean Front Vacationing - Groton/Mystic

MimiRating, 5 stars2 weeks ago
The house was very clean, with a beautiful, large, well stocked kitchen. The view was lovely and it was wonderful hanging out on the deck. The beds were very comfortable. The house would be a little more practical if one of the bedrooms had two beds, so more people could sleep in the actual bedrooms. The pull out beds were not as comfortable and the bed in the loft is only accessible with a ladder. However, for a small group or people who aren’t picky about their sleeping arrangements it is a fantastic place to stay. You can’t beat the view and proximity to the water!
Top guest favorite
Home in South Kingstown
4.97 out of 5 average rating, 100 reviews

Stunning Waterfront Cottage with Big Yard & Dock!

OscarRating, 5 stars1 week ago
It was a very relaxing home surrounded by beautiful waterfront wildlife( a pair of swans and other birds ) and views. It was well worth the stay and I would like to stay there again and I would recommend it to family and friends in the future.
Top guest favorite
Home in South Kingstown
5 out of 5 average rating, 143 reviews

Waterfront Secluded Home with Dock

SusanRating, 5 stars1 week ago
I hate to say too many great things since I kind of feel like I want to keep this a secret. This is our second time staying here. The location is awesome — spectacular views from any of the many windows in this contemporary style house. The beds are decent and there’s lots of beach stuff (chairs, towels, umbrella) plus kayaks w/life vests. Well equipped kitchen and good size dining room table. And did I mention the views?… of course I did, but it’s worth mentioning again! A great beach about a mile away. Dining choices are limited now because of the tragic fire at the Matunuck Oyster Bar a few nights before our arrival. Our host was kind enough to send us an email prior to our arrival to inform us of this sad event. We had reservations there for our first night at the house. Since we are pretty casual, the food at Captain Jack’s and Jim’s Dock is decent… but sure missed Matunuck Oyster Bar and our hearts go out to all the staff as the busy summer season was about to begin.
Top guest favorite
Home in Haddam
5 out of 5 average rating, 21 reviews

Luxe Lake House Retreat Between Boston & New York

DelphineRating, 5 stars1 week ago
The place is so peaceful and gorgeous, almost like being in a nature preserve but not far from anything either. We saw deer, a fox, a heron, and lots of adorable chipmunks. It was the perfect place to stay during a graduation weekend where the town was bustling and we needed a place to decompress when not on campus. The lawn is simply stunning, and there are incredible views on the the pond and the sky from pretty much every room in the house. We were there during a wet spring and everything was green and fresh. It must be spectacular in the fall or during a snowy winter. Shawn is a super kind, attentive host. We hope to come back in 3 years for our next graduation! Thank you for letting us stay here!

Waterfront condo rentals

Guest favorite
Condo in North Fork
4.84 out of 5 average rating, 106 reviews

Beautiful condo on Long Islands Northfolk

LauraRating, 5 stars1 month ago
We very much enjoyed our stay at the Cliffside for our wedding weekend! Alice was very flexible with us, which we appreciated because getting married is chaotic enough LOL. Would highly recommend staying here. The unit was spotless and had a wonderful view. We could not have asked for a better stay!
Top guest favorite
Condo in The Hamptons
5 out of 5 average rating, 228 reviews

Montauk Waterfront Condo w/ Sunset Views

MarieRating, 5 stars4 days ago
we had s great time staying at the apartment! it was way more spacious than we thought from the pictures, the balcony was amazing, you‘ll have sun through the whole day. Doug was a phenomenal host! We got their by LIRR and back with the hampton jitney. We rented two bikes in Montauk and it was amazing exploring the area by bike. Cannot recommend this area and the airbnb enough!
Guest favorite
Condo in Uncasville
4.94 out of 5 average rating, 32 reviews

Cozy Vacation Villa 5 minutes from Mohegan

WilliamRating, 5 stars2 weeks ago
The stay was very peaceful, friendly neighbors. The scenery was great, Desiree was there for any concerns we had, and with timely response. I would anyone that want a pleasurable stay while in Norwich, this is the place to be. Thanks again, for a wonderful stay. William & Potreen
Condo in North Fork
4.89 out of 5 average rating, 152 reviews

Beautiful Waterview Condo on the North Fork of LI

SarahRating, 5 stars4 weeks ago
Mia’s place is excellent. Exactly what the listing describes and more — Mia is a great host and super attentive despite us being a last minute booking, she even helped us through a tough time late in the day when I thought my daughter’s stuffie had been picked up by the maid service. Above and beyond!
Superhost
Condo in The Hamptons
4.89 out of 5 average rating, 9 reviews

Endless Summer Studio Condo w Balcony Bayview

StephenRating, 5 stars21 months ago
We really enjoyed staying at Lynn’s place! Very clean and had a great view of the ocean from the deck. Lynn was very responsive and made the experience seamless. We would definitely stay with Lynn again.
Superhost
Condo in North Fork
4.9 out of 5 average rating, 125 reviews

Seaside Summer Escape –2BR Waterfront Condo w/Pool

DebbieRating, 5 stars3 weeks ago
We had a great time at Julie’s place. Would love to visit again…perhaps in the Fall. Loved the balcony overlooking the Sound. Julie was very responsive to my questions. She got back to me immediately. I would highly recommend Julie’s home!
Guest favorite
Condo in North Fork
4.92 out of 5 average rating, 139 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

MorganRating, 5 stars1 week ago
We had a great stay! Instructions were clear and the home had everything we needed.
Top guest favorite
Condo in Uncasville
4.98 out of 5 average rating, 81 reviews

King Bed - hot tub - saunas - 1 mile Mohegan Sun

DanielleRating, 5 stars2 weeks ago
We stayed at Taylor's place because of the proximity to Mohegan Sun! What we got was an adorable space in a beautiful neighborhood that was super close to the concert venue! It truly is a nice neighborhood! It was peaceful with beautiful water views and fountains! Everything in the house was nice and clean! It was awesome that there were little snacks and water! Such a nice touch! It was super easy to get into the villa, easy to lock and just a great spot! Keyless..perfect! Thank you, Taylor! We will return if you'll have us again!

Quick stats about waterfront rentals in Old Saybrook

  • Total rentals

    30 properties

  • Nightly prices starting at

    ﺩ.ﺇ404 before taxes and fees

  • Total number of reviews

    890 reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

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