
Cottage holiday rentals in Old Saybrook
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Top-rated cottage rentals in Old Saybrook
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Popular amenities for cottage rentals in Old Saybrook
Cottage rentals with a hot tub

Waterfront cottage overhanging the water!
We thoroughly enjoyed our time at the cottage. It was so very peaceful and we loved being literally right around n the water! Slept amazingly well and the cottage was just lovely! Robert was also a great host. 5 stars all around and we hope to return again!

Walk/Bike to East Hampton Village & Ocean Beaches
I had a wonderful weekend at Andrew’s place in East Hampton. It was gorgeous, perfect location, perfect layout, and such a central location to everything. It was incredibly clean and organized and the backyard was beautiful for relaxing. Andrew was also a terrific host- he left us beverages, was super communicative and flexible and I’m so happy I stayed here. Hopefully I’ll rent again soon!!

Litchfield-Hot Tub-Shops & Eats-Vineyards-Hikes
Took a getaway to Martin's cottage for a long weekend and could not have been happier. It was immaculately clean and the hot tub was ab amazing way to relax. I look forward to being back.

Lakefront Summer Escape | Cool Tub | Fire Pit
Absolutely stunning views and peaceful vibes at this sweet cottage!!! Totally exceeded my expectations. Book now or you’ll regret it!!!

♥CozyGetaway-Narragansett-15min to Newport-HotTub♛
We had a wonderful stay at Leann’s! The home was absolutely lovely—clean, cozy, and beautifully decorated. The amenities were just what I needed for a relaxing getaway. Leann was a great host, and we truly can’t wait to come back. Highly recommend!

Cozy Getaway | Pet Friendly | Litchfield Cty
Kelsey’s cottage was exactly as described. It was so beautifully decorated & had everything that we would need. We had a wonderfully relaxing weekend & hope to do it again soon.

NEW - Hot Tub - Mohawk Mtn - Appalachian Trl
This place was absolutely beautiful and clean. A very comfortable stay! I would definitely stay here again!

Lakeside cottage with beautiful views up the lake!
We always love going to this cottage. It’s our favorite. It’s actually one of our favorite places. To go a few times a year winter summer. We just spent memorial weekend there. A little doggies loved it. Home away from home so cozy. Bobby the host is wonderful. My daughter boyfriend came up and they absolutely loved it and my son came from Texas to spend one night. It was his first time there he loved it. We already planning on going back. Fantastic getaway. If you need to distress and want calmness. This is the place to come to. And the town of Mystic has great restaurants Like I said it’s our favorite place to come to and I’ve been to quite a few…. Just got home today and I’m seeing if I can book some sometime in October to go back we love it.
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.

Foxfire Hill: A Bit of Luxury in the Countryside
The cottage exceeded our expectations in all respects. It is very well laid out, clean, easy to access and better than described. The site itself is very nice--detached from the main house and garage. There is a small kitchen garden just outside the back door and nice plantings of flowers all around. Mike and Meryl were very responsive to a few questions we had. I come to the area twice a year to race at nearby Lime Rock Park and I will certainly try to reserve the property for all future stays. This is the nicest AirBNB property I have ever experienced.

Private and Serene home close to I-84 and shopping
One of the nicest hosts I have ever met. Peaceful area, cute house. Hard to believe that large stores and restaurants are only a few miles away, plus Shake Shack, Trader Joes and Whole Foods. The only problem I had was with my ancient cell phone. I could get test messages, but not phone calls.

Mystic, CT Pet-Friendly Cottage with Hiking Trails
My sister, dog and I stayed at the cottage for the weekend and had a great experience! Erika is a wonderful host and the property is beautiful. The cottage itself was exactly as pictured. Breakfast in the inn, cooked with natural and organic ingredients, is an absolute must. The location of the inn is great as well, with direct access to the Lantern Hill trail (which our dog loved) and only a short drive from downtown. Would definitely recommend staying here!

Cozy Cottage by the pond
What a perfect place to explore Southern Connecticut from. Easy to find and easy access to all points of interest. Collis P. Huntington state park is across the street and is an incredible perk. Many easy to walk trails with plentiful wildlife and peaceful serenity. Would recommend and stay again in the future. Jamie is an awesome host, so thoughtful and responsive!!

Montauk Oceanview
Always love staying at Ron’s. It’s so peaceful. Perfect location and beautiful Ocean views with a short ride if you need to go to town. Montauk Music Fest is a must. Amazing talent and great way to see all Montauk venues. Ron so great to have as a host!

Adorable cottage
Angela was a great host and very accommodating after an unfortunate personal event we encountered just after arriving. The cottage was very comfortable and immaculately clean. Love the keyless entry. Neighborhood is quiet and we felt extremely safe. Deer pass through the yard throughout the day and what's more beautiful than that!!! We absolutely recommend Angela as a host and would not hesitate to book again in the future.

Lakefront Cozy Oasis 2BR w/ stunning sunset views
We recently stayed here for my Husband's Graduation Ceremony at Post University and Mother's Day as we are from Philadelphia. We brought our senior dog and everything was accommodating. The most beautiful views and overall relaxing visit. Would definitely recommend! And hopefully we will be back soon!
Private cottage rentals

Peaceful Oceanfront Cottage
Wonderful place to get away from the busy life. We found it relaxing and a convenient 20 min drive to the academy We will definitely book again!

A Beach House Gem
We continue to visit Rose’s house for our yearly weekend girls getaway. It’s the perfect cozy beautiful place to catch up with friends and relax. Rose is an amazing host!

SeaStar Beach House Old Saybrook
Our family had a wonderful weekend at Robin’s home. The location was perfect for a fall getaway with access to plenty of restaurants, and fun family activities. The home is lovely with beautiful yard space directly overlooking the nature filled marsh. The home is clean and comfortable with all needed items during our stay. The city of New Haven is also close by for cultural activities, Yale and museums. We highly recommend this Airbnb and hope to return again.

Beautiful Updated Cottage walk to the Beach
The cottage is very well maintained, beautifully decorated, super clean and spacious. You’ll find everything you need there! The location is great, the beach is a 5 minutes walk, neigh bits are very friendly and quiet. Within a short drive you’ll find lots of restaurants, all is listed by Joe in the cottage! We loved spending a few days here and would love to come back!

Adorable cottage close to beaches and downtown
My family were coming to the commencement so we stayed at John’s place for several days. The house is at a very quiet place surrounded by woods yet easy to find from the main road, and has easy access to I-95. The house was bigger than we thought and can accommodate six or even more people. It has everything we need like dishwasher, washer and dryer, etc. John also kindly provided grounded coffee and drinks in the fridge. It was an excellent experience!

Bucolic Farm On A Country Road
We could not have asked for a nicer place to stay~~~~clean, comfortable, woke up every morning hearing the bird’s singing. Felt like home. And Lori was a wonderful host! Thank you!

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!

Chic Coastal Retreat with Short Walk to Beach
Our time at the Coastal Cottage was so comfortable, quiet, and relaxing! Adorable decor inside the cottage, several beautiful areas to visit along the coast nearby, and easy access to the beach. Plus Alexandra and Stephen were such great hosts who were very easy to communicate with. Highly recommend checking out this spot if you plan a visit to the coastline of Connecticut!
Quick stats about cottage rentals in Old Saybrook
Total rentals
20 properties
Nightly prices starting at
₹6,863 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
- Charlestown Beach
- Fairfield Beach
- Southampton Beach
- Yale University
- Foxwoods Resort Casino
- Napeague Beach
- Cooper's Beach, Southampton
- Walnut Public Beach
- Shinnecock Hills Golf Club
- TPC River Highlands
- Woodmont Beach
- Amagansett Beach
- Ocean Beach Park
- Quotonset Beach
- Giants Neck Beach
- Point Judith Country Club
- Seaside Beach
- Jennings Beach
- Silver Sands Beach
- Blue Shutters Beach
- Bushnell Park
- Bayview Beach
- Outer Beach at Smith Point County Park