Cottage vacation rentals in Old Saybrook

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Top-rated cottage rentals in Old Saybrook

Guests agree: these cottages are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage in Ledyard

4.91 out of 5 average rating, 109 reviews

Mystic, CT Pet-Friendly Cottage with Hiking Trails

Unwind at this peaceful, private Cottage with a fenced garden courtyard. Enjoy onsite hiking trails, EV chargers, an outdoor lounge, hammocks, firepit, lawn games, and a gas grill. Your stay includes organic breakfasts and eco-friendly amenities. Just 6 miles from Mystic, the Cottage is your dream escape. Book your stay now and create lasting memories with your pet! ❤️The Cottage books fast for weekends, holidays, & all of summer and fall. We recommend booking soon to guarantee your getaway.❤️

Top guest favorite

Cottage in Mystic

4.98 out of 5 average rating, 242 reviews

Mystic Cottage Retreat, near downtown

This recently renovated cottage is at the top of a quiet lane with a sweeping meadow view. Single level. Two bedrooms sleep four (queen and two twin beds); new, well-equipped kitchen and one bath, open living area, deck and patio. Light and spacious. Working fireplace, central A/C; W/D; expanded cable TV and wifi; off street parking for two cars. Market/deli nearby; pleasing walk (less than a mile from center of Mystic)- restaurants, shops, marinas, etc. Near Amtrak station. Great retreat!

Guest favorite

Cottage in Cornwall

4.93 out of 5 average rating, 147 reviews

Newly Built Cottage in Housatonic Valley

This newly built modern cottage is located on a historic railroad street nestled in a charming village within the Housatonic River Valley. There are beautiful river views from the front porch, deep woods off the back deck, a white marble kitchen with new appliances, and a dedicated parking spot. Escape the city and surround yourself in this quiet valley and the calm of small village life, located just 2 hours from NYC. This location offers year-round access to nature & outdoor activities.

Guest favorite

Cottage in Ledyard

4.89 out of 5 average rating, 195 reviews

Waterfront cottage overhanging the water!

Come relax at this cute and cozy cottage overhanging a large and beautiful lake! Whether it's a family trip, a couple's getaway, or a best friends reunion, this place has something for everyone. From relaxing on the deck with a beautiful view, to kayaking and canoeing, or swimming in the summer, there is much fun and peaceful relaxation to do at the cottage. Also, it's just a 10 minute drive to Mystic, wineries, orchards, the shoreline, restaurants, and 5 minutes to Foxwoods casino.

Guest favorite

Cottage in Goshen

4.94 out of 5 average rating, 123 reviews

Country Cottage in Goshen

Quaint country cottage, with beautiful hardwood floors, screened in porch, claw foot bathtub and lots of antiques set on a naturally landscaped 1 acre property. The original cottage was built in 1932, but was completely renovated in the last 5 years. 650 square feet with a bedroom, bathroom, lounge on the 2nd floor loft, and an open floor plan with living area, dining area and kitchen on the first floor. French doors lead from the dining area to a large screened in porch.

Superhost

Cottage in Litchfield

4.86 out of 5 average rating, 336 reviews

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

This vintage style cottage offers guests a comfortable and convenient stay in Litchfield with it’s range of amenities. Essential amenities include air conditioning, cooking basics, a dedicated workspace, dishes and silverware, a dryer, hair dryer, heating, hot tub, kitchen, TV, washer, and Wi-Fi. 5 Min - Litchfield Town center 9 Min - Arethusa Dairy farm- Restaurant 10 Min - White Memorial Conservation Center 8 Min - Bantam Lake 19 Min - Mohawk Mountain Ski Area

Guest favorite

Cottage in Montauk

4.87 out of 5 average rating, 100 reviews

Secluded 1Br cottage on the lake, close to Ditch

This is the best of Montauk living, right by the lake, close to Ditch, and with an incredible, lush front yard suitable for outside dining or having a couple friends over for dinner. Walk down to the lake to enjoy the sunset, or stroll over to the Crow's Nest for drinks or dinner. No need to drive, it's well within walking distance. Join the many that have experienced the magic of our cottage at South Lake.

Guest favorite

Cottage in Mystic

4.97 out of 5 average rating, 104 reviews

Historic Mystic, CT - Harbor View Landing - The Cove Waterfront Cottage

The Cove unit is a queen-sized studio, waterfront cottage, with custom tiled private bathroom. This cottage comes equipped with retro mini-fridge, microwave, Nepresso coffee maker, HD TV, Amazon smart speaker, free wi-fi as well as a complimentary bottle of wine and water. Matouk linens and luxury Molton Brown bath products. Beach towels provided for complimentary water activities.

Guest favorite

Cottage in Goshen

4.95 out of 5 average rating, 150 reviews

Stuart Cottage/Minutes to Mohawk Ski Area

The Stuart Cottage is located on the grounds of the Mary Stuart House Bed and Breakfast. Owned by Mary and managed by Elizabeth, the cottage has one bedroom, wifi and plenty of charm...truly the perfect place to relax in a rustic, low-key location in the heart of the Litchfield Hills. Mohawk Mountain and Tyler lake are just a short car ride.

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What guests are saying

Cheerful, private cottage in Essex village.

4.96 out of 5 average rating, 51 reviews6 months ago

This was the perfect place for my quick trip to Essex, CT. I was traveling alone and this little one bed/one bath was great for my needs. It was a little challenging to find at first, but once you figure it out, it's easy peasy - and I appreciated that it's set so far back off the street. The house is close enough to town that you can walk if you want to, and it's just an overall great location. I'll be back!

Cottage in Essex

What guests are saying

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

4.97 out of 5 average rating, 151 reviews1 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.

Cottage in North Fork

What guests are saying

Game Room-Mins to Beach&Boardwalk-Walk to Marinas

5 out of 5 average rating, 15 reviews1 month ago

Erin’s place was perfect for our family weekend away! It was incredibly clean, stocked with everything we needed, and was a lovely space. The game room was a huge bonus, our son absolutely loved playing the arcade games all weekend :) Erin is a great host. Would definitely stay here again!

Cottage in Waterford

What guests are saying

New Shoreham Cottage

4.89 out of 5 average rating, 90 reviews5 months ago

This was our second stay with Cathy. We hope to stay at her home next year too. That’s how much we love the house, the location, and trust the host to be responsive and helpful, Wonderful hosts. Always responsive, considerate, helpful. Beautiful place to be. Feels like home. The surroundings beautiful, the shore, the island, and the town, the fields and meadows. The house is very comfortable. There is everything you would need for a comfortable, relaxing, fun stay.

Cottage in New Shoreham

What guests are saying

Waterfront Beach Cottage

4.88 out of 5 average rating, 147 reviews6 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!

Cottage in Woodmont

What guests are saying

Sun Filled Cottage

4.94 out of 5 average rating, 18 reviews3 weeks ago

My husband and I stayed at the cottage for 3 months and enjoyed our time very much. We were very happy from every perspective: The cottage had all the equipment we needed and wished for. We sometimes used the fireplace and loved the bed/couch. The cottage is perfect to rest and focus. We enjoyed to have so much nature around us. We took a walk in the close park with a lake almost every day. We liked to live at a small farm with dogs, chicken and goose. Debbie and Kirk were always there when we needed them and also made us internationals feel welcome. They explained and helped us proactively e.g. changed regional weather circumstances. We also regularly got eggs from the chicken what was always a nice surprise. Communication/ interactions were always easy and friendly. I recommended my work to plan future stays for assignments in this Airbnb. In our opinion it is better than a hotel: Very comfortable, cozy, close to nature and a special American experience. Thanks a lot Debbie and Kirk

Cottage in Southbury

What guests are saying

Charming Fairfield Beach 3BR Cottage By The Sea

4.97 out of 5 average rating, 119 reviews8 months ago

We enjoyed our stay! Such easy access to the beach was so convenient. You’re definitely better off venturing out after high tide to enjoy the most amount of beach and there are a lot of shells that make being barefoot challenging. We did arrive after major storms which could have contributed to that. The house was spotless with everything you need to be comfortable! We did not utilize the outdoor space but definitely would have if the weather was drier! Definitely would stay here again.

Cottage in Fairfield

What guests are saying

walk to bay, woods cottage

5 out of 5 average rating, 31 reviews5 months ago

We had the most wonderful and peaceful fall weekend at Brooke’s cozy cottage to celebrate our anniversary, and it was truly unforgettable! The cottage itself is beautifully decorated and felt like a warm home away from home. Brooke went above and beyond to make our stay special, leaving us complimentary champagne and wine to kick off our celebration. The location was perfect for enjoying the crisp fall air and stunning foliage, providing the peaceful retreat we were hoping for. We can’t recommend this place enough and will definitely be back for another stay!

Cottage in Hampton Bays

What guests are saying

2 BR East Matunuck cottage 7 min walk to beach!

4.88 out of 5 average rating, 112 reviews6 months ago

We had a great stay at Greg's place. Potter pond is gorgeous and a kayaking paradise, and the walk to the beach was amazing. Being so close to great restaurants was also amazing. This is a gem of a location for a beach vacation. One note- I had thought we'd be able to launch our kayak at the water right behind the unit, but you need to walk them a little bit over to the kayak launch. Not a big deal, but make sure you bring a kayak cart if you think you'll need one.

Cottage in South Kingstown

What guests are saying

EASY BEAT

4.95 out of 5 average rating, 204 reviews1 week ago

This is our second trip to Easy Beat and we love it. It’s perfect for me, my partner, and our two dogs. It’s always hard finding a place that not only allows dogs, but is a dog lover themselves. The extra dog bowls, doggie bags, and treats was really a nice gesture. The yard was nice and big for them to explore and get their energy out. Early and easy check in was very appreciated. Close to Mohegan, Foxwoods, and Mystic Shoppes. We tried Paul’s Pasta bc it was in John’s welcome binder and it was delicious! A must try! This house is so unique with random decorations. There’s plenty of cool design ideas to see. If you’re looking for a place to stay that’s centrally located to the casinos with a great space for your pups this is the place to be! Looking forward to coming back next year!

Cottage in Groton

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