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Vacation rentals in Old Saybrook

Book unique cottages, vacation rentals, and more on Airbnb

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Popular amenities for Old Saybrook vacation rentals

Stay near Old Saybrook's top sights

Florence Griswold Museum65 locals recommend
The Katharine Hepburn Cultural Arts Center52 locals recommend
The Griswold Inn49 locals recommend
Westbrook Outlets44 locals recommend
Connecticut River Museum38 locals recommend
Big Y World Class Market34 locals recommend

Old Saybrook beach vacation rentals

Guest favorite
A sunlit view of a sandy beach stretches towards the horizon, with gentle waves lapping at the shore. Colorful umbrellas dot the sandy area, and a wooden walkway runs parallel to the beachfront. In the distance, sailboats can be seen on the calm water.
Home in New London
4.93 out of 5 average rating, 352 reviews

Amazing Beach House

RichardRating, 5 stars1 week ago
This is a terrific place to stay. Close to the beach, 20 minutes from Mystic, lots of sleeping space, world’s greatest shower head. The place was ready before our check-in time. Crystal sent excellent directions for getting inside, using the TV, and everything. We had a wonderful time.
Guest favorite
Outdoor seating is arranged on a wooden deck, featuring sleek loungers. Surrounding planters add greenery, while the view stretches to the calm water and distant horizon. Sunlight brightens the area, enhancing the serene ambiance of the beachfront setting.
Cottage in North Fork
4.97 out of 5 average rating, 151 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

RashaRating, 5 stars1 week ago
We absolutely loved our quick getaway from the city at Kate’s lovely home. It is hard to articulate in words just how beautiful of a home and location this was. It was truly magical. We were very comfortable as a family traveling with young children. Despite the weather being a bit chilly, we had a wonderful time soaking the views and discovering “treasures” by the water. We cannot wait to come back again soon.
Superhost
A wide-angle view captures the beach and waterfront community, showcasing houses lined along the shore. A sandy beach meets calm waters, with a jetty extending into the sea. Fluffy clouds float in a clear blue sky above the scenic landscape.
Guesthouse in Milford
4.92 out of 5 average rating, 205 reviews

Chic Coastal Retreat: Modern Apt Steps from Beach

JoyRating, 5 stars1 month ago
Nice ground floor apartment across the street from the beach and 2 blocks from the state park. Love the outdoors. And Delores and her brother were amazing. Friendly, responsive, and helpful.
Superhost
A panoramic view showcases a tranquil beach scene under a double rainbow arching over the sea. Gentle waves lap at the shore, while a sandy beach space with sparse grass is visible. A blue umbrella and chairs provide a welcoming spot for relaxation.
Cottage in Milford
4.78 out of 5 average rating, 32 reviews

Cheerful 2 bedroom cottage on beach

MatthewRating, 5 stars9 months ago
This house is absolutely perfect. It's clean, charming, has everything you need. The beautiful back yard has plenty of space and good stuff for kids to play with. Also, it's about a 30 second walk to the beach... neighbors are out on their patch of beach but yours is yours to yourself. It's perfect. We cannot wait to come back.
Guest favorite
A large beach house is visible, featuring multiple gables and a spacious deck with balcony. The facade is painted in light grey, complemented by white trim. In the foreground, sandy beach leads toward the house, framed by green grass and shrubs on either side.
Home in West Haven
4.95 out of 5 average rating, 19 reviews

Beach House steps from sand & Amazing Views

YvesRating, 5 stars7 months ago
Toute notre famille a adoré cette merveilleuse villa et son jardin au bord de la mer. La maison est magnifique, très spacieuse, très belle, très confortable, très bien équipée. Tout est bien pensé, bien organisé, très propre, très bien rangé. Nous avons vécu le rêve américain ! Une très belle expérience que nous recommandons avec enthousiasme.
Guest favorite
The image captures a serene view of the ocean from a wooden porch, showcasing calm waters and a sandy beach. A neatly maintained lawn extends to the shoreline, with a few small boats visible in the distance under a clear blue sky.
Home in East Lyme
4.96 out of 5 average rating, 186 reviews

Beachfront Paradise

DavidRating, 5 stars4 weeks ago
We stay at Patti's place twice a year for a time of reflection. The location is peaceful and restful, right on the water. Patti always has a plate of cookies waiting for us and lets us know about any changes. We had a cold, wet first day, so were particularly delighted to be able to use the new gas fireplace, which kept everything warm and cozy. We're booked in for late fall already!
Guest favorite
A modern kitchen features an expansive island with four bar stools. Stylish pendant lights hang above the island, illuminating the spacious countertop. Stainless steel appliances, including a large oven and coffee maker, complement the crisp white cabinets and sleek backsplash.
Home in Milford
4.92 out of 5 average rating, 25 reviews

Modern Beach Mood 2!

RomanRating, 5 stars7 months ago
Wow! What a place! We were all blown away by the home from the living arrangement to the small details. The patio was amazing for enjoying the nights and the walk to the beach was very manageable. The patio space in the back was perfect for enjoying the cool nights. Cole was fantastic in hosting with setting the expectations with extra videos after booking. Cole was also very responsive and understanding. Next time I am booking in the Milford area, this will be the first listing I check for availability.
Guest favorite
A shaded porch featuring a gray wooden floor extends towards the water, with hanging planters displaying vibrant flowers. Ocean views are visible in the distance, and a small blue boat is anchored along the shoreline. Soft light creates gentle shadows across the space.
Home in Woodmont
4.98 out of 5 average rating, 43 reviews

Beachfront paradise- come, stay, relax!

TheoRating, 5 stars3 months ago
we rented La Spiaggia in December, and while it's mostly going to be more beautiful and better in the summer (since it's a beach house) it was still perfectly fine in the winter; well insulated and with good strong heaters. speaking of the beach I can't stress enough of how close this place is to the water; I'm talking literally ten steps to the sand. I would certainly recommend the place as a great summer getaway!

Cottage rentals in Old Saybrook

Guest favorite
Cottage in Voluntown
4.94 out of 5 average rating, 207 reviews

Lakeside Cottage in the Forest

BeckyRating, 5 stars2 weeks ago
we had a wonderful weekend stay at your home, felt very welcoming , had everything we needed. Thank you so much!
Top guest favorite
A cozy cottage is presented with a wooden deck and a sloped roof. The deck features a dining table surrounded by chairs. Lush greenery and neatly trimmed bushes surround the pathway leading to the cottage, with a serene lake visible in the background.
Cottage in Hopkinton
4.98 out of 5 average rating, 138 reviews

Lakeside Cottage in Hope Valley, RI

JanetRating, 5 stars3 months ago
This was the ideal location for my husband and me to spend the holidays with our family who live across the lake. Will and John gave us a warm, friendly welcome and Quinn also checked in to make sure we settled in and had everything needed for a comfy cozy stay. It was easy to communicate with everyone and the location felt peaceful and private but not isolated. I can't imagine a more ideal experience and cannot thank Quinn enough for making this stay the best ever we've had with Airbnb!
Guest favorite
A telescope is positioned on a tripod near a row of three windows, offering views of the serene waters of Long Island Sound. Light streams in, highlighting a wooden table and a striped armchair in the cozy seating area.
Cottage in Woodmont
4.88 out of 5 average rating, 147 reviews

Waterfront Beach Cottage

Bridie AnneRating, 5 stars6 months ago
Allyson’s home was in a beautiful location. We loved the uniqueness of the home. We came for a music festival and were surprised to find out it was a neighborhood porch festival. The neighbors let us know and invited us to join in the fun - as they had 3 bands playing on Saturday. It was so much fun and gave us a glimpse of the welcoming neighborhood. Now we want to come back next year for PorchFest!
Top guest favorite
Cottage in Guilford
4.99 out of 5 average rating, 136 reviews

"Red House on the Knoll" at Indian Cove

MaryRating, 5 stars1 week ago
My family and I loved staying at Gail’s place! We grew up in Madison and were back for a visit. It was such a great place and allowed us to re-live many fond memories of growing up in the area!
Top guest favorite
A patio area features dark wicker seating arranged around a low table, with a wood dining set positioned nearby. A large umbrella provides shade, while lush greenery surrounds the space, creating a serene outdoor environment for relaxation.
Cottage in Redding
5 out of 5 average rating, 103 reviews

Star Cottage

DavidRating, 5 stars3 months ago
Great time at Star Cottage! Five Stars! So comfortable and warm. Especially over the holidays. Nikki is a great host.
Guest favorite
A charming street scene captures vintage-style buildings, adorned with holiday wreaths and white lights. Soft snowfall creates a serene atmosphere, while a clock tower is visible in the background, contributing to the quaint character of the area.
Cottage in Goshen
4.94 out of 5 average rating, 123 reviews

Country Cottage in Goshen

VioletteRating, 5 stars2 months ago
Such a sweet cottage with great decor and beautiful kitchen + nice quiet outdoor area. Lovely to go to with your mate. We felt right at home here!
Guest favorite
The exterior of the modern cottage is presented, featuring a sleek, dark facade accentuated by landscaped stone pathways. A spacious porch offers a welcoming entry, complemented by large windows that provide natural light. Surrounding hills are visible in the background.
Cottage in Cornwall
4.93 out of 5 average rating, 147 reviews

Newly Built Cottage in Housatonic Valley

MaryanneRating, 5 stars1 month ago
We loved our stay and hope to return next year!! Thank you so much!
Guest favorite
The cozy bedroom features a sloped wooden ceiling and warm, natural light filtering through a window. A bed with a checkered duvet is flanked by two bedside lamps, while a woven basket sits at the foot, adding a touch of rustic charm.
Cottage in Goshen
4.95 out of 5 average rating, 150 reviews

Stuart Cottage/Minutes to Mohawk Ski Area

SherryRating, 5 stars1 month ago
The cottage was just as lovely as it looked! We really appreciated the bakery treat waiting for us upon arrival. Such a cozy place to stay with our little dog. Everything was super clean and we loved the decor. Thanks again!

House rentals in Old Saybrook

Guest favorite
A charming Cape Cod cottage is showcased, featuring a light gray shingled exterior and blue door. The front yard is adorned with green grass and small shrubs, while steps lead to the entrance. Tall trees frame the property, providing a sense of privacy.
Home in Sag Harbor
4.85 out of 5 average rating, 160 reviews

Sag Harbor House for rent.

MichaelRating, 5 stars7 months ago
Ed was great at communicating, house was everything we could have asked for. Would definitely book again!
Guest favorite
The exterior of a two-story single-family home is depicted, featuring beige siding and a centered front door. Lush green grass surrounds the walkway leading to the entrance, with a mailbox positioned at the pathway. A nearby tree and hedges provide additional greenery.
Home in East Haven
4.89 out of 5 average rating, 101 reviews

Welcome To Piper's Rest

JamesRating, 5 stars2 weeks ago
It was wonderful stay and I’d go back anytime
Top guest favorite
A single-story home is situated on a well-kept lawn with lush greenery and small bushes lining the front. The exterior features light-colored siding and a dark roof, complemented by multiple large windows that enhance natural light.
Home in Cheshire
5 out of 5 average rating, 132 reviews

Pool House

MelissaRating, 5 stars3 months ago
This was our second time back to the pool house and it was amazing, again. We thinks of everything to make you feel welcome. Milk and eggs in the fridge. Muffins and croissants waiting for you. Pristine home. Fully stocked kitchen. I was even able to host a few family members for Christmas dinner and had everything I needed to make a lovely dinner. We also travel with two dogs and Sue is so accommodating, making our pups feel right at home. Thank you, Sue, for making our holidays away from home so peaceful and enjoyable.
Top guest favorite
A traditional two-story house is framed by well-maintained greenery and shrubs. A paved driveway leads to the entrance, while a detached garage is visible to the side. The exterior features white siding with red trim and multiple windows, creating a welcoming appearance.
Home in Southampton
4.96 out of 5 average rating, 119 reviews

4 Bed, 2 Bath, Southampton, L.I.

BrandonRating, 5 stars9 months ago
This was my second time staying here, and probably won’t be the last. A perfectly wonderful Hamptons home, with a beachy, rustic charm. It’s close to all, yet on a quiet street with a great backyard. David is a fantastic host, everything was spelled out clearly and the home was spotless.
Guest favorite
A dining room table with eight chairs is set beneath ambient lighting. The room opens to a cozy living area featuring a comfortable sofa and blue curtains. A doorway leads to a well-lit kitchen, enhancing the home's spacious layout.
Home in New London
4.94 out of 5 average rating, 134 reviews

House in NL near CGA, Sub Base, Mohegan Casino

MeaganRating, 5 stars4 months ago
Our family opted for a trip to New London to reconnect with our family for Thanksgiving. We were able to utilize the beautiful dining room for our dinner . We loved staying at Rosa’s place and were very comfortable . Just a note - there is only one bathroom and it is on the second floor ( as are all the bedrooms) We made this work but can be difficult with a larger family . It would definitely not deter me from booking again! This place was beautiful. The surrounding area and ease of access was comforting ! Would definitely stay here again .
Top guest favorite
The exterior of a charming two-story house is presented, featuring light siding and dark shutters. Window boxes adorned with blue flowers are visible. A small porch with a door leads into the home, accompanied by a stone pathway and neatly landscaped shrubs.
Home in Old Saybrook
4.97 out of 5 average rating, 121 reviews

Year Round Beach House in Old Saybrook, CT.- Pets

SueRating, 5 stars4 days ago
Laurie s place is very nice, spacious and clean. Plenty of space to eat, hang out and 2 bath. The fenced in yard is great for dogs or kids. We weren't in full summer season so we're not taking advantage of the beach and water options but they offer alot. Allowed for an early check in which was great as we were in town for a memorial service.
Top guest favorite
A two-story home features a grey exterior with white trim and a bright blue front door. Sturdy stone steps lead up to the entrance, flanked by well-maintained landscaping that includes green plants. The property is bordered by a wooden fence, offering privacy.
Home in Westerly
4.98 out of 5 average rating, 132 reviews

Cute and Close to Beaches and Town

HayleyRating, 5 stars1 month ago
This was a perfect place to stay with our dog and 2 small children. The fenced in yard was secure. You can easily walk to many restaurants, or like us, just for fun with the dog and kids. Joe was immediately responsive when I messaged him with questions and when I inquired about a late check out, he was happy to let us stay a few hours longer which was really nice.
Guest favorite
A bright living area is illuminated by natural light through large windows. A decorative black wall with a welcome message adds character. A comfortable seating arrangement and dining space is featured. Art pieces are displayed, enhancing the creative ambiance of the space.
Home in Montauk
4.99 out of 5 average rating, 101 reviews

6 minute walk to Ditch Plains Beach

EmilyRating, 5 stars3 months ago
We had a wonderful time! Lisa was incredibly proactive with all check-in and check-out instructions. The location was exactly what we wanted-- close to downtown and walkable to a beach. The rooms were great, and we loved the space downstairs for socializing. Everything was beautifully decorated and set the stage for a perfect weekend escape. We hope to be back soon!

Quick stats about vacation rentals in Old Saybrook

  • Total rentals

    120 properties

  • Nightly prices starting at

    ﺩ.ﺇ184 before taxes and fees

  • Total number of reviews

    3.4K reviews

  • Family-friendly rentals

    100 properties are a good fit for families

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

Frequently Asked Questions

  • What types of vacation rentals are available in Old Saybrook?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Old Saybrook. From over 90 house rentals to over 20 cottage rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.

  • Are there vacation rentals with a dedicated workspace in Old Saybrook?

    Yes! Work meets play with ease at over 60 vacation rentals in Old Saybrook featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Old Saybrook?

    Four-legged friends are welcome in Old Saybrook. Choose from more than 40 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in cottage rentals in Old Saybrook?

    Experience the best of Old Saybrook with our cottage rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Old Saybrook have a gym?

    Absolutely! We offer over 10 house rentals with a gym in Old Saybrook. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Old Saybrook have a bbq area?

    Absolutely! We offer over 30 house rentals with a bbq area in Old Saybrook. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Old Saybrook have self check-in?

    Absolutely! We offer over 30 house rentals with self check-in in Old Saybrook. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly cottage rentals in Old Saybrook?

    Old Saybrook has more than 10 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore