Waterfront vacation rentals in Old Saybrook

Find and book unique waterfront accommodations on Airbnb

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Popular amenities for Old Saybrook waterfront rentals

Waterfront apartment rentals

Top guest favourite
Apartment in Northport
4.99 out of 5 average rating, 144 reviews

Amazing one bdrm flat at the beach!

DavidRating, 5 stars2 weeks ago
Jeanette is a wonderful host. She met us on our arrival and gave us a tour of our rental ensuring that she answered any questions. She is very responsive and quick to answer any follow up. questions or concerns. The space is beautifully decorated and comfortable. The location is great, across the street from Long Island Sound and bordering a large nature preserve. All this and easy access to shops, groceries, and restaurants. We highly recommend this rental.
Guest favourite
Apartment in Stonington
4.95 out of 5 average rating, 283 reviews

Mystical Ocean View in Historic Stonington Borough

JanetRating, 5 stars4 weeks ago
This was possibly the coolest Airbnb I have ever stayed in- the details of this place make you feel like you’re someplace truly special. Sam was amazingly responsive. The descriptions are accurate- that 3rd story spiral staircase is no joke - regardless, I was very comfortable and absolutely loved the setting. Will be back!
Top guest favourite
Apartment in Stonington
4.97 out of 5 average rating, 214 reviews

Mystic River Getaway - Walk To Downtown & Seaport!

ChristinaRating, 5 stars1 week ago
We thoroughly enjoyed our week at this charming home. The location truly is perfect - we walked over to the Seaport one day and took many walks into the downtown area for shopping, meals at amazingly good restaurants, ice cream, and bake shops. Anthony and Kelly were wonderful hosts - the home was just as described and their communication was clear and friendly- just what you want from hosts. We couldn't have asked for more and would be happy to stay here again.
Superhost
Apartment in South Norwalk
4.9 out of 5 average rating, 82 reviews

Water View SONO 2 Bedroom Walk to Metro & Dining

TammiRating, 5 stars2 days ago
We were in town for a figure skating competition. The layout was perfect for enough privacy traveling with a teammate and the house was super clean and cozy. House was super quaint and beautifully restored!!! We loved the picturesque area, proximity to shopping malls and great restaurants AND local skating rinks. One of our best stays ever, thanks to the attentive host — we will absolutely book again.
Top guest favourite
Apartment in Fairfield
5 out of 5 average rating, 72 reviews

Bright, private 1,000 sq. ft. 1-Bedroom Apartment

WendyRating, 5 stars1 month ago
The whole experience was perfect. There were even fresh flowers to greet me. The location is easy, a beautiful neighborhood that is very quiet and safe. I'm ready to return!
Guest favourite
Apartment in Middlebury
4.92 out of 5 average rating, 118 reviews

Cozy Apartment with Water View of Brook

JulieRating, 5 stars1 day ago
Our stay was extremely quiet until the upstairs neighbors returned. We don't have kids or pets so we're very used to quiet. Getting used to hearing upstairs neighbors took getting used to for me. The place was chock full of supplies, coffee, Scrabble and welcoming decor. The bed was outstandingly comfortable. The bathroom was modern and creative! The outdoor patio, activities and view of the creek were impressive. This is definitely on our "to return to" list.
Top guest favourite
Apartment in Milford
4.97 out of 5 average rating, 62 reviews

Steps to the Beach. Lovely 2-Bedroom apt

BrennaRating, 5 stars8 months ago
Perfect house for a family/couple visit to the beach. It was great for my kids and I. We loved the space that the house offered and how close it was to the beach. Everyone was very pleasant that we spoke to. The house was clean, safe and felt like a home away from home.
Guest favourite
Apartment in Middletown
4.83 out of 5 average rating, 158 reviews

Lakeside apartment 2.5 miles from Wesleyan campus!

RichardRating, 5 stars3 months ago
Always nice to stay with Mark and Tina. Wonderful people. Very convenient location for us. Beautiful setting. We keep coming back!!

Waterfront house rentals

Guest favourite
Home in Waterford
5 out of 5 average rating, 6 reviews

Direct Waterfront / Riverside

JosephRating, 5 stars7 months ago
Jim’s place was great, with plenty to see in the area. We ended up spending most of the time enjoying the little beach and kayaks. Very cute house with plenty of room and we’ll stocked kitchen. The grill made for a perfect Labor Day cookout looking out at the water. Would stay again.
Guest favourite
Home in Amagansett
4.93 out of 5 average rating, 14 reviews

Amagansett, Waterfront retreat

DanielleRating, 5 stars7 months ago
My family had a wonderful time at Robert’s home. The house was clean and cozy and the view of the water was peaceful. He was super communicative and friendly and check in/out was a breeze. The house is in a great area and super close to East Hampton, Amagansett, and Montauk. Highly recommend!
Guest favourite
Home in Groton
4.94 out of 5 average rating, 193 reviews

True Ocean Front Vacationing - Groton/Mystic

KellyRating, 5 stars3 weeks ago
The pictures don't do this place justice! The home itself is gorgeous and the view is stunning. The neighborhood is peaceful and it was perfect for me and four friends to stay the weekend.
Top guest favourite
Home in South Kingstown
5 out of 5 average rating, 134 reviews

Waterfront Secluded Home with Dock

MireyaRating, 5 stars3 days ago
It is a beautiful, secluded home with a wonderful view of and access to the water on Potter's Pond. The house felt comfortable with a lot of thought for details - the kitchen was well-equipped, lots of pillows on the beds, high quality and a lot of towels in the closets, night-lights, puzzles and games. Made for a wonderful and comfortable stay. We definitely plan on trying to come back!
Guest favourite
Home in East Haven
4.96 out of 5 average rating, 27 reviews

Home in East Haven directly on Waterfront

ShukhratRating, 5 stars3 months ago
Beautiful house beautiful ocean view! We had a wonderful time with our family, we would like to come back again summertime Thank you
Guest favourite
Home in Shoreham
4.86 out of 5 average rating, 104 reviews

Lush Waterview rainforest retreat

KarenRating, 5 stars4 months ago
The location and views from Phil's place are absolutely beautiful. It was a cozy place to stay and unwind while visiting family in the area. The beach and pathway to it are wonderful. Phil was very responsive to our couple of questions. We would happily go back when in the area again!
Guest favourite
Home in South Kingstown
5 out of 5 average rating, 39 reviews

Absolutely stunning! New water front house

BrendaRating, 5 stars1 week ago
Beautiful house, great location. Walkable to the beach. Ume was very responsive and proactive in reaching out with instructions and recommendations. The welcome gift was a really nice touch. Would look to book again!
Guest favourite
Home in Narragansett
4.8 out of 5 average rating, 10 reviews

Cozy Waterfront Cottage with a Boat Dock

AmberRating, 5 stars9 months ago
We really enjoyed our stay at Jake's place on the salt pond! The location is wonderful and close to everything-beaches, restaurants, grocery store etc. The house is tiny but felt spacious enough for all 5 of us to have our own space. The newly finished lower level was a bonus. The view was so serene and a nice reprieve after busy days at the beach.

Waterfront condo rentals

Condo in North Fork
5 out of 5 average rating, 6 reviews

Water front, sunsets, sail boats, Wi-fi, birds

CharlesRating, 5 stars7 months ago
John and Cathy are amazing hosts. This was our second consecutive summer stay in their condo and it does not disappoint. The place and the amenities they provide are amazing and they are a wonderful couple who respects your privacy but are there for anything you need. I recommend anyone to stay here and know they would want to return. Thank you John and Cathy for making our second summer with you a fantastic vacation!
Guest favourite
Condo in North Fork
4.84 out of 5 average rating, 106 reviews

Beautiful condo on Long Islands Northfolk

LauraRating, 5 stars2 days 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
Condo in Montauk
5 out of 5 average rating, 222 reviews

Montauk Waterfront Condo w/ Sunset Views

MollyRating, 5 stars1 week ago
Absolutely wonderful stay and host. I've stayed at dozens of Airbnbs and this is one of my favorites! Doug's place is even better in person than the photos. We were a little nervous taking our first trip away with our baby, but it was extremely clean and comfortable, and Doug was so kind and responsive. The condo complex has a lovely boardwalk for taking walks, and the deck furniture was so comfortable to lounge in and take in the beautiful view. We hope to be back!
Guest favourite
Condo in Norwich
4.94 out of 5 average rating, 31 reviews

Cozy Vacation Villa 5 minutes from Mohegan

JillianRating, 5 stars3 months ago
My husband and I stayed at Desiree’s place for New Years weekend. The space was beautiful, clean, comfortable and perfect for our getaway. Close to the casino and spa and anything you need. Would definitely recommend!
Guest favourite
Condo in North Fork
4.89 out of 5 average rating, 149 reviews

Beautiful Waterview Condo on the North Fork of LI

AnnaRating, 5 stars5 months ago
Such a beautiful condo by the water! Too bad we stayed in November, we would have enjoyed the terrace way more! Mia was so responsive and helpful with my questions prior to the weekend at her place.
Superhost
Condo in Montauk
4.89 out of 5 average rating, 9 reviews

Endless Summer Studio Condo w Balcony Bayview

StephenRating, 5 stars20 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.
Guest favourite
Condo in North Fork
4.92 out of 5 average rating, 138 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

RoxanaRating, 5 stars6 months ago
The place was perfect nice and clean what I like the best is the it was close to the beach to go for a walk.
Top guest favourite
Condo in Norwich
4.97 out of 5 average rating, 76 reviews

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

RoshiniRating, 5 stars4 weeks ago
This villa is a perfect spot for a weekend getaway. Though in a condo complex, the villa itself felt private. The villa is just a few minutes walk from the clubhouse, which has a jacuzzi and pool (open in summers), and the Norwich Inn. We did not get to go to the clubhouse, but the Inn had a great spa and restaurants. The villa is also a 5 minute drive from Mohegan Sun and is accessible via Uber. The fireplace made the villa very cozy. Would definitely stay again!

Quick stats about waterfront rentals in Old Saybrook

  • Total rentals

    30 properties

  • Nightly prices starting at

    $152 CAD 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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