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Compare 106 Cottages in Chester with updated reviews, rates, and availability.

Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

10.0 out of 10, Exceptional, (102)
"We really enjoyed our stay. Beds, linens, towels all super comfortable. Kitchen bright and useful. Bathrooms spotless. 2 minute walk to cute beach. Tons of stuff to do in the area. Great, private backyard well appointed with portable fire pit, grill, furniture. Lots of kid games and books and puzzles in house. Need functional carbon monoxide detector. "
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

Cozy cottage near downtown Clinton, Marina & Hammonasset Park

10.0 out of 10, Exceptional, (68)
"We really enjoyed our time away at this wonderful cottage!"
Cozy cottage near downtown Clinton, Marina & Hammonasset Park

Beach Bungalow, large porch, 1/2 mile to the water.

8.4 out of 10, Very Good, (5)
"Very nice and comfortable property "
The price is AED 753
AED 1,443 total
includes taxes & fees
30 Nov - 1 Dec
Beach Bungalow, large porch, 1/2 mile to the water.

Luxury Cottage walking distance to Saybrook Point Marina, 2 King Beds

9.6 out of 10, Exceptional, (33)
"Lovely little cottage in a pretty, quiet neighborhood. Once you find it down the little lane, it's a great location to be in. Not far from town and close to the water, we really enjoyed relaxing at the house and in the backyard. Highly recommend."
Luxury Cottage walking distance to Saybrook Point Marina, 2 King Beds

Charming Old Saybrook Cottage < 1 Mi to Beach

10.0 out of 10, Exceptional, (23)
"Old Saybrook is a very comfortable, clean, and well kept home. Sizeable bedrooms and baths, comfortable beds, and ample linens provided. Basically, check in using the security code and that's it! We are so happy we chose Old Saybrook for our stay, as it made for a very comfortable, and relaxing trip. We were not there long enough to have enjoyed the back yard grill, but surely would have if we could. BTW...the host is GREAT!!!"
Charming Old Saybrook Cottage < 1 Mi to Beach

Charming Deep River Vacation Rental on Star Lake!

7.0 out of 10, Good, (4)
"Nice relaxing small house for a quick weekend getaway. Plenty of space in the kitchen and bedrooms. The shower is very very small, especially with a curtain that you kind of have to hold back away from you while you shower. If you like very firm beds youre in luck, the matresses are pretty firm. I would bring your own pillows as those provided were very thin. Other than that, its the perfect spot for a getaway. We had a wonderful relaxing weekend."
Charming Deep River Vacation Rental on Star Lake!

Private Guest House w/ Deck + Spectacular Views!

10.0 out of 10, Exceptional, (23)
"We loved our trip. The cottage is beautifully done and the views incredible. We appreciated the hospitality extended by our host (and Nico the dog!) and enjoyed exploring the nearby woodland. Our kids are already asking if we can go back and visit again. "
Private Guest House w/ Deck + Spectacular Views!

Waterfront! Charming 4BR Cottage on the Niantic River!

9.6 out of 10, Exceptional, (59)
"We loved the antique house filled with family treasures. We spent many peaceful hours by the firepit looking over the river. The location is great, close to restaurants and stores. Amy is a wonderful host, checking in with us to make sure everything was okay. Thank you Amy. "
Waterfront! Charming 4BR Cottage on the Niantic River!

Shalom Cottage with private beach rights.

9.0 out of 10, Wonderful, (17)
"Loved the overall stay and experience. The private beach access is a bonus"
The price is AED 312
AED 623 total
includes taxes & fees
26 Nov - 27 Nov
Shalom Cottage with private beach rights.

Beach access Cozy Cottage

9.8 out of 10, Exceptional, (6)
"Very clean and adorable place providing all one needs for peace and respite. I would return again."
Beach access Cozy Cottage

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

10.0 out of 10, Exceptional, (13)
"This was a great spot to stay with my wife, another couple, and my dog! The house is small - especially downstairs. But it is extremely well thought out and space is used as effectively as can be. Upstairs had 2 good sized bedrooms with king beds and a nicely renovated bathroom with a great shower. The house is located in a small, cute, and a bit of an unusual neighborhood. Very quiet. Very safe feel. But not too good for much dog walking and parking is super tight. Owner was very good with...
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

70 Year old cottage on 2.8 acres, stunning views and sunsets

8.4 out of 10, Very Good, (6)
"We all liove the various Connecticut shore towns, and Ild Lyme was delightful. We revisited some favorite spots, and discovered a few new ones. The vintage appliances were particularly nice to find, and looking at old photos, we realized that the original cottage was really 100 years old!"
70 Year old cottage on 2.8 acres, stunning views and sunsets

"Salt 'n' Lyme" - Walk to everything !

9.4 out of 10, Exceptional, (29)
"Nice place in quiet neighborhood with great owner. "
"Salt 'n' Lyme" - Walk to everything !

Enchanted Waterfront Cottage

9.0 out of 10, Wonderful, (19)
"The location was perfect. Very comfortable."
Enchanted Waterfront Cottage

Waterfront Cottage in Branford

10.0 out of 10, Exceptional, (87)
"The house was perfect for our annual getaway. We are a group of nine women who have been friends for over 45 years. The large well stocked kitchen with amazing view of the water and fireplace made our Friendsgiving meal memorable! The outdoor hot tub, fire pit, and deck with comfy seating topped off the weekend. Great location, plenty of parking, responsive host. 5/5 stars! "
Waterfront Cottage in Branford

The Dream Location for Your Perfect Vacation

9.8 out of 10, Exceptional, (16)
"beautiful quiet spot on the beach, great place to stay."
The Dream Location for Your Perfect Vacation

Classic Cottage in Best Private Community in Old Lyme CT.

10.0 out of 10, Exceptional, (26)
"A wonderful cottage in a great community at Point O Woods Beach. The host was incredibly helpful, responsive and did everything to make our stay a memorable one. Thank you so much!"
Classic Cottage in Best Private Community in Old Lyme CT.

A beach cottage gem...

10.0 out of 10, Exceptional, (60)
"Driftwood is everything we imagined and more. The cottage is beautifully and tastefully appointed, inside and out. We loved walking into the open dining/kitchen/livingroom area and seeing nothing but ocean out the large picture window. The cottage sits right on the beach. Listening to the gentle lapping of the waves and sitting in Adirondack chairs on the front porch overlooking the ocean brought us peace and relaxation. Everyone we met was friendly and welcoming. The owner, Annie, answered any...
A beach cottage gem...

Guilford Carriage House at Granite Lodge!

10.0 out of 10, Exceptional, (8)
"We had a couple of out of town events in the are this past weekend, and it was also my birthday, so we decided to stay somplace special. The Granite Lodge Carriage hose was all of that! Beautifully decorated and furnished with lots of special touches from the host! We would definitely recommend, and will!"
Guilford Carriage House at Granite Lodge!

Waterfront Cottage w/ Sunroom + Patio & Grill

8.0 out of 10, Very Good, (5)
"Overall it was a nice relaxing stay. Nice and clean. Lots of sun through the back windows. Amenities were much appreciated, in kitchen, bathroom and bedrooms."
Waterfront Cottage w/ Sunroom + Patio & Grill
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Chester

Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino

10.0 out of 10, Exceptional, (28)
"The only ‘concern’ we had was that the heated pool wasn’t heated. Ice cold. Also, one other minor issue was that there were no coffee creamers supplied to the unit. Other than that, the stay was pretty good and room ess quiet and comfortable. "
The price is AED 643
AED 1,259 total
includes taxes & fees
24 Nov - 25 Nov
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino

Private Guest House w/ Deck + Spectacular Views!

10.0 out of 10, Exceptional, (23)
"We loved our trip. The cottage is beautifully done and the views incredible. We appreciated the hospitality extended by our host (and Nico the dog!) and enjoyed exploring the nearby woodland. Our kids are already asking if we can go back and visit again. "
Private Guest House w/ Deck + Spectacular Views!

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

10.0 out of 10, Exceptional, (13)
"This was a great spot to stay with my wife, another couple, and my dog! The house is small - especially downstairs. But it is extremely well thought out and space is used as effectively as can be. Upstairs had 2 good sized bedrooms with king beds and a nicely renovated bathroom with a great shower. The house is located in a small, cute, and a bit of an unusual neighborhood. Very quiet. Very safe feel. But not too good for much dog walking and parking is super tight. Owner was very good with...
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much do cottages in Chester cost?
Cottages in Chester range between AED 312 and AED 753 per night. These retreats offer a chance to get in touch with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Chester?
There are 106 cottages in Chester. Whether you’re vacationing with the family or planning a getaway with your buddies, Expedia can help you find the ideal space to enjoy the surrounding nature.
Why book your cottage in Chester with Expedia?
We think that vacays should be easy, so if you’re seeking cottages in Chester at the perfect price, Expedia can help. Stick to the budget and check in to a wallet-friendly option far from the rush of the city, or book a 5-star cottage to pamper your favorite people.
How can I find cheap cottages in Chester?
With Expedia’s useful filter tool, locating cheap cottages in Chester couldn’t be simpler. To view properties that are friendly on the wallet, narrow your search results by star rating, budget and amenities.