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Cottage holiday rentals in Old Saybrook

Find and book unique cottages on Airbnb

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Popular amenities for cottage rentals in Old Saybrook

Cottage rentals with a hot tub

Guest favourite
Cottage in Ledyard
4.88 out of 5 average rating, 207 reviews

Waterfront cottage overhanging the water!

JenRating, 5 stars1 week ago
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!
Superhost
Cottage in East Hampton
5 out of 5 average rating, 4 reviews

Walk/Bike to East Hampton Village & Ocean Beaches

JimmyRating, 5 stars8 months ago
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!!
Superhost
Cottage in Litchfield
4.86 out of 5 average rating, 345 reviews

Litchfield-Hot Tub-Shops & Eats-Vineyards-Hikes

ZacharyRating, 5 stars1 week ago
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.
Top guest favourite
Cottage in Plymouth
5 out of 5 average rating, 18 reviews

Lakefront Summer Escape | Cool Tub | Fire Pit

AllysonRating, 5 stars4 days ago
Absolutely stunning views and peaceful vibes at this sweet cottage!!! Totally exceeded my expectations. Book now or you’ll regret it!!!
Top guest favourite
Cottage in Narragansett
5 out of 5 average rating, 223 reviews

♥CozyGetaway-Narragansett-15min to Newport-HotTub♛

JudelieRating, 5 stars1 week ago
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!
Guest favourite
Cottage in Bethlehem
4.98 out of 5 average rating, 103 reviews

Cozy Getaway | Pet Friendly | Litchfield Cty

LyndaRating, 5 stars1 month ago
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.
Superhost
Cottage in Kent
4.84 out of 5 average rating, 233 reviews

NEW - Hot Tub - Mohawk Mtn - Appalachian Trl

BrieRating, 5 stars4 weeks ago
This place was absolutely beautiful and clean. A very comfortable stay! I would definitely stay here again!
Guest favourite
Cottage in Ledyard
4.93 out of 5 average rating, 253 reviews

Lakeside cottage with beautiful views up the lake!

KerriRating, 5 stars1 week ago
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

Guest favourite
Cottage in Middlefield
4.92 out of 5 average rating, 246 reviews

Lake Beseck cottage

NicoleRating, 5 stars5 months ago
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.
Top guest favourite
Cottage in Sharon
4.93 out of 5 average rating, 180 reviews

Foxfire Hill: A Bit of Luxury in the Countryside

MichaelRating, 5 stars1 week ago
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.
Guest favourite
Cottage in Newtown
4.93 out of 5 average rating, 252 reviews

Private and Serene home close to I-84 and shopping

SherrieRating, 5 stars1 week ago
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.
Top guest favourite
Cottage in Ledyard
4.91 out of 5 average rating, 112 reviews

Mystic, CT Pet-Friendly Cottage with Hiking Trails

OliviaRating, 5 stars4 weeks ago
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!
Top guest favourite
Cottage in Redding
4.93 out of 5 average rating, 263 reviews

Cozy Cottage by the pond

LeeRating, 5 stars1 week ago
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!!
Guest favourite
Cottage in Montauk
4.91 out of 5 average rating, 598 reviews

Montauk Oceanview

SusanRating, 5 stars3 weeks ago
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!
Superhost
Cottage in Rocky Point
4.93 out of 5 average rating, 160 reviews

Adorable cottage

JoAnnRating, 5 stars6 months ago
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.
Guest favourite
Cottage in Plymouth
4.94 out of 5 average rating, 118 reviews

Lakefront Cozy Oasis 2BR w/ stunning sunset views

RachelRating, 5 stars4 weeks ago
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

Superhost
Cottage in Waterford
4.82 out of 5 average rating, 96 reviews

Peaceful Oceanfront Cottage

DeborahRating, 5 stars8 months ago
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!
Guest favourite
Cottage in Westbrook
4.9 out of 5 average rating, 87 reviews

A Beach House Gem

JaimeRating, 5 stars7 months ago
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!
Guest favourite
Cottage in Fenwick
4.92 out of 5 average rating, 39 reviews

SeaStar Beach House Old Saybrook

Simone & KirstenRating, 5 stars7 months ago
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.
Top guest favourite
Cottage in Westbrook
4.99 out of 5 average rating, 68 reviews

Beautiful Updated Cottage walk to the Beach

FlorenceRating, 5 stars1 week ago
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!
Top guest favourite
Cottage in Madison
4.94 out of 5 average rating, 33 reviews

Adorable cottage close to beaches and downtown

YaoRating, 5 stars2 weeks ago
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!
Guest favourite
Cottage in Lyme
5 out of 5 average rating, 18 reviews

Bucolic Farm On A Country Road

K.K.Rating, 5 stars3 days ago
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!
Superhost
Cottage in Westbrook
4.52 out of 5 average rating, 21 reviews

Remodeled Cottage Private Old Kelsey Point Beach

JillRating, 5 stars10 months ago
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!
Guest favourite
Cottage in Old Lyme
4.92 out of 5 average rating, 63 reviews

Chic Coastal Retreat with Short Walk to Beach

BrittneyRating, 5 stars3 weeks ago
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

Destinations to explore