
Cottage vacation rentals in Old Saybrook
Find and book unique cottages on Airbnb
Top-rated cottage rentals in Old Saybrook
Guests agree: these cottages are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Old Saybrook cottage rentals
Cottage rentals with a hot tub

Luxury cottage by the sea with hot tub and pool
We loved this airbnb and stayed for 3 weeks. It sits right on the edge of the marsh with an extraordinary view. We greatly enjoyed how a short walk away is Chaffinch Island, which is a gorgeous park full of tides pools and hackberry trees. The space was clean and comfortable and Mary was a fantastic host. You can see a lighthouse on an island 3 miles out sea from all the rooms, even the main bed.

Cozy Lakefront Cottage w/Swim Spa & Firepit
Absolutely loved my stay here. The space was beautiful, peaceful, and had everything I needed. I would definitely come back again!

Lakefront Summer Escape | Hot Tub & Lake Access
Loved this stay! The views by the lake were absolutely stunning, and the hot tub was the perfect way to relax. The place was clean, cozy, and had everything we needed. Highly recommend!

Bridgehampton Cottage Close to Town, South of HWY
Great space and would be back!

Cozy Getaway | Pet Friendly | Litchfield Cty
Such a cozy space!!! My small family really did enjoy our peaceful stay. I would definitely book again when in the area. I felt such peace and serenity sitting under the stars, in front of the crackling campfire. It was me and the hubby with 2 of our girls ages 10 and 16. They loved the hot tub and s’mores:). Thanks for the stay.

Lakefront Cottage Complete with Kayaks!
Place was very well cared for, kitchen and bathrooms were spotless and had everything needed. The views of the lake are GORGEOUS. Felt like home, we had a great time even with the bad weather.

Lakeside cottage with beautiful views up the lake!
Our stay at the cottage was lovely. Beautiful view from the living room of the pond, and even better from the dock while soaking in the hottub! Lots of cozy blankets and the woodstove kept us warm and toasty all weekend. The kitchen was lovely for preparing a nice dinner. All in all, this was a beautiful stay, and we appreciate Bobby’s hosting us, and his prompt attention to any questions we had. We would love to come back and visit again!

Lovely 2 BR Beach House No. Shore
Great spot for a long weekend! Wonderful location close to the beach and local wineries. Richard was a great host offering lots of recommendations and clear instructions for check in and using available amenities.
Pet-friendly cottage rentals

Lake Beseck cottage
Was the perfect little get away for us. And it was nice to find a place that accommodated the dogs so well. We appreciated being able to get to places easily but at the same time have a peaceful place to return to.

Welcome to The Holly at Amston Lake
This place is the perfect getaway location, especially for a quiet relaxing weekend. Great host who was super responsive and flexible with me trying to check in early.

Pet-Friendly Private Beach Oceanfront Cottage A/C
Highly recommend! Beautiful space with an incredible location right on the water! Stunning sunsets and views! So quiet and peaceful. Appreciated the very clear directions from Elizabeth in terms of the house and local area! Can’t wait to return!

Foxfire Hill: A Bit of Luxury in the Countryside
What a restful beautiful setting. Beautiful views. We really enjoyed watching the hens roam the yard. A super clean space, roomy and comfortable. Some cute towns nearby like Millerton, Hillsdale, Copake, New Preston, Millbrook. Kent Falls close too.

Serene Waterfront Cottage
As always, we love our stay at the cottage. It’s becoming our home away from home when visiting our son. Thanks for all our goodies! Always a great surprise! Have a wonderful Christmas. We’ll see you next year I hope.

Cozy Cottage by the pond
My husband and I had a great stay. James and Rose are super helpful hosts. It’s a great place to relax and enjoy nature. Walking distance to a lovely park they recommended with tons of hiking trails and very quiet.

Spring Sale|CozyCottage|Walk to Beach|Pet-friendly
We had nice weekend at the cozy cottage. We loved that it was pet friendly and a short walk to the beach. Cameron was very friendly and responsive. She offered great suggestions for food and activities.

Charming Southampton Light filled Cottage
Wonderful stay at Wendy’s cottage. We appreciated the tasteful design and cozy feel of the place. Just felt right at home. Kitchen was well equipped for making dinner and a couple breakfasts. The neighborhood is beautiful - about a half block walk to an adorable lake - and conveniently a 10-15 drive to many other places. Highly recommend!
Private cottage rentals

Wash Pond Cottage
A true getaway weekend at Wash Pond house. The scenery is beautiful from the large deck overlooking the pond, right down to the dock at the base of the water. The rustic cottage's soothing atmosphere in this secluded area is everything one could ask for. The house has all the essentials and more to make you feel right at home. Katrina is an incredible host; friendly, helpful and attentive. I highly suggest the Wash Pond experience.

Cottage Ease.
This cute cottage’s was exactly what we were looking for. Our stay was short but Meredith gave us great suggestions for places to eat to help us avoid wasting our minimal time searching. On a fall weekend the neighborhood was quiet. It was a really nice weekend stay for us.

Beautiful cottage on East End
Vincent’s place was great for my husband, myself, our baby and my parents to stay when visiting Jamesport for a wedding. Beautiful cottage, close to everything, and Vincent was very easy to communicate with. Would stay here again

Chic cottage on lush, secluded acre by the beach.
We had a wonderful stay at Mischa’s home. The house was truly stunning - beautifully decorated and clean. Mischa has clearly thought about all of the little details that make a stay memorable - the kitchen was well stocked and the place was so cozy.

Renovated beach cottage a block from private beach
April’s cozy beach cottage was perfect for my elderly parents. Everything was spotless, and although tiny, the kitchen was fully stocked with a large refrigerator and full stove, microwave etc. both the bed and the sofa were v comfortable and most importantly, April made sure there was AC in every room, even the cute porch. There’s an outdoor shower which is super convenient. You can easily walk to the beach, go to the arcade, kokomos, a crepes place and the carousel and gift shop. Very peaceful retreat. Must also mention how cheerfully it’s decorated and how spotlessly clean! Just lovely.

Remodeled Cottage Private Old Kelsey Point Beach
Cheryl's place was adorable! I felt right at home in the cosy open concept living space. My mom crashed the weekend portion of the trip which was nice. My cat Mushu had a wonderful time and we even went outside. The beach was about a four minute walk for me, and a breathtaking view as you approach. Cheryl had everything necessary and mentioned. Next time I'll be sure to bring coffee filters and sugar. There were unexpected amenities too like paper towels and trash bags, and candles. There were also tons of spare toiletries like shaving cream and shampoo and conditioner and body wash. Thanks again!

Waterfront Cottage, Fort Pond MTK
Wonderful all around!! Thank you again to Noah who was terrific. Lovely place :)

Huge Montauk Cottage W Private Full Bath & Shower
Can’t say enough about Michael and our stay. He made everything seem-less and was super helpful with recommendations and accommodations. We can’t wait to come back next year or this summer! Hopefully many years to come! 5 stars!
Quick stats about cottage rentals in Old Saybrook
Total rentals
20 properties
Nightly prices starting at
$80 before taxes and fees
Total number of reviews
650 reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Beach
- Yale University
- Foxwoods Resort Casino
- Ocean Beach Park
- Quotonset Beach
- Giants Neck Beach
- Cooper's Beach, Southampton
- Clinton Town Beach
- Woodmont Beach
- Shennecossett Beach
- Shinnecock Hills Golf Club
- Seaside Beach
- Walnut Public Beach
- Shoreham Beach
- Horton Lane Beach
- Burlingame State Park
- Mystic Seaport Museum
- South Pine Creek Beach
- Outer Beach at Smith Point County Park
- La Ronde Beach Club Inc
- Rogers Beach
- Road F Beach
- Jennings Beach
- The Connecticut Golf Club
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