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Waterfront holiday rentals in Old Saybrook

Find and book unique waterfront rentals on Airbnb

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Popular amenities for waterfront rentals in Old Saybrook

Waterfront apartment rentals

Guest favourite
Flat 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 favourite
Flat in Stonington
4.95 out of 5 average rating, 289 reviews

Mystical Ocean View in Historic Stonington Borough

YuwenRating, 5 stars4 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 favourite
Flat in Stonington
4.97 out of 5 average rating, 217 reviews

Mystic River Getaway - Walk To Downtown & Seaport!

SarahRating, 5 stars1 week 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 favourite
Flat in College Hill
4.97 out of 5 average rating, 205 reviews

Jennifer’s Historic Downtown Loft

DallasRating, 5 stars4 days ago
I had a great stay at Jennifer’s place in PVD! The space was clean, stylish, and exactly as described. It was super easy to access and check-in was a breeze. The location was perfect—close to some really fun spots, great restaurants, and local attractions. Whether you’re visiting for a quick getaway or a longer stay, this place is a solid choice. I’d definitely stay here again!
Guest favourite
Flat in Middlebury
4.92 out of 5 average rating, 121 reviews

Cozy Apartment with Water View of Brook

EvelindaRating, 5 stars1 week 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!
Guest favourite
Flat in West Granby
4.9 out of 5 average rating, 131 reviews

Majestic Farmhouse Private & Peaceful Guest Apt.

CindyRating, 5 stars9 months ago
This was a quick trip to the area to break up the drive to a further destination. Joy's little 18thc apartment was perfect. Joy met and explained everything needed, and was very helpful with local suggestions for dining and activities.Was'nt here long enough to experience any of the hiking trails,.etc but truly seems like a place I'd like to return. if you're lucky, you will meet the inimitable Baloo!
Guest favourite
Flat in Middletown
4.82 out of 5 average rating, 163 reviews

Lakeside apartment 2.5 miles from Wesleyan campus!

ElisaRating, 5 stars1 week ago
The apartment was beautiful and as soon as we walked in I could feel myself relax. The view is stunning and the apartment is warm and inviting. We reserved the apartment on very short notice and Mark was so helpful and responsive. Highly recommend!
Top guest favourite
Flat in Milford
4.98 out of 5 average rating, 104 reviews

The Pond Mill Retreat w/ 2 Bdrms & Pool

JudyRating, 5 stars1 week 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 favourite
Home in East Lyme
4.94 out of 5 average rating, 64 reviews

Lakeside bliss

KatherineRating, 5 stars6 days ago
We had an absolute PERFECT stay here! First off- the house. This home is so charming in every way. We loved the way it’s decorated and laid out, and it’s so cozy, clean and beautiful. You are truly able to relax here. Also, the bed is extremely comfortable, the water pressure is great, and the A/C works very well. However, perhaps the best part of this house is the view! There are sliding doors in the living room and bedroom, and the view of the lake is breathtaking. The area is super safe and quiet, and you are in walking distance to downtown Niantic and the Boardwalk which you cannot beat! Also only about 20 minutes from Mystic. I cannot forget to mention how amazing our host, Katie, was! Super attentive and responsive with messaging, and she was even here doing yard work when we arrived so she greeted us which was such a nice touch. Overall, we will DEFINITELY be looking to stay here again! Loved every minute of it.
Guest favourite
Home in Coventry
4.98 out of 5 average rating, 113 reviews

Cozy cottage 5 minutes from UConn

JdRating, 5 starstoday
Immaculate space. Location and views are incredible. Check in was easy, hosts were very communicative and you can tell they put a great deal of energy into their home. They also included fresh eggs from their farm. We were obsessed with it and will definitely rebook.
Guest favourite
Home in Centerport
4.94 out of 5 average rating, 153 reviews

The Harbor House: Beachfront Home 1 hour from NYC

JiagengRating, 5 stars1 month ago
Beautiful layout and views: The living room extends to an expansive harbor view as we opened the door. When we turn around the lofty A frame transitions into the bedroom connected by a wooden spiral stair. Interior appliances are good and functional. Plenty of Pillows and blankets to get cozy. The Weber Grill is great to use. We used public transport and Uber and it was pretty easy to get around - 15 mins to nearby scenes and restaurants.
Guest favourite
Home in Montville
4.91 out of 5 average rating, 128 reviews

Thames River Cottage · Near Casinos + USCGA

MelRating, 5 stars2 weeks ago
Great space, accurate description
Guest favourite
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 favourite
Home in Groton
4.94 out of 5 average rating, 198 reviews

True Ocean Front Vacationing - Groton/Mystic

MimiRating, 5 stars3 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 favourite
Home in South Kingstown
4.97 out of 5 average rating, 100 reviews

Stunning Waterfront Cottage with Big Yard & Dock!

OscarRating, 5 stars2 weeks 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.
Guest favourite
Home in Southampton
4.96 out of 5 average rating, 170 reviews

Waterview+Pool, FreeForDogs! Kayaks/PingPong/Bikes

ChristiRating, 5 stars1 month ago
We had a wonderful two day stay at Roger and Amy’s place. It was fantastic- such a beautiful, inviting home. Our kids had a blast in the heated pool- we could barely get them to come out despite it being under 60 degrees out! The kitchen was stocked with more than just kitchen basics- the spice cabinet had soo many different choices ! It was probably the most perfect AirBnb experience I’ve had and we travel plenty.

Waterfront apartment rentals

Guest favourite
Apartment 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 favourite
Apartment in Montauk
5 out of 5 average rating, 229 reviews

Montauk Waterfront Condo w/ Sunset Views

RachelRating, 5 stars6 days ago
We loved Montauk - low key, wild and upmarket at the same time. This apartment was perfect, super quiet yet near everything and loved seeing wild deer from the terrace
Guest favourite
Apartment in Norwich
4.94 out of 5 average rating, 32 reviews

Cozy Vacation Villa 5 minutes from Mohegan

WilliamRating, 5 stars3 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
Superhost
Apartment in Montauk
4.89 out of 5 average rating, 9 reviews

Endless Summer Studio Condo w Balcony Bayview

StephenRating, 5 stars22 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
Apartment in North Fork
4.9 out of 5 average rating, 125 reviews

Seaside Summer Escape –2BR Waterfront Condo w/Pool

DebbieRating, 5 stars4 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 favourite
Apartment in North Fork
4.92 out of 5 average rating, 139 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

MorganRating, 5 stars2 weeks ago
We had a great stay! Instructions were clear and the home had everything we needed.
Top guest favourite
Apartment in Norwich
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!
Guest favourite
Apartment in Old Lyme
4.91 out of 5 average rating, 34 reviews

Forecastle at Soundview · Beach+OceanView+Sunrise

NolanRating, 5 stars1 day ago
Super nice place good communication. All around worth it!

Quick stats about waterfront rentals in Old Saybrook

  • Total rentals

    30 properties

  • Nightly prices starting at

    $141 SGD 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

Destinations to explore