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Check prices for these dates

Next weekend
2 May - 4 May
In two weeks
9 May - 11 May
In one month
23 May - 25 May
In two months
20 Jun - 22 Jun

Compare 140 Cottages in Chester with updated reviews, rates, and availability.

Charming 3-bedroom cottage in Old Saybrook with WiFi and AC
Living area

Charming 3-bedroom cottage in Old Saybrook with WiFi and AC

Charming 3-bedroom cottage in Old Saybrook with WiFi and AC
Charming 3-bedroom cottage short walk to Chalker Beach
Smart TV, books

Charming 3-bedroom cottage short walk to Chalker Beach

Charming 3-bedroom cottage short walk to Chalker Beach
Private Guest House w/ Deck + Spectacular Views!
Property grounds

Private Guest House w/ Deck + Spectacular Views!

10.0 out of 10, Exceptional, (25)
"Meetings with friends who were staying at Mohegan Sun which was 20 minutes away. Pretty views, comfortable property. Would definitely return "
Private Guest House w/ Deck + Spectacular Views!
1-bedroom cottage with Grove Beach 🏖️ access.
Smart TV

1-bedroom cottage with Grove Beach 🏖️ access.

9.2 out of 10, Wonderful, (25)
"Everything was wonderful and the location was just as advertised. Will definitely consider staying again. "
1-bedroom cottage with Grove Beach 🏖️ access.
The gardners Cottage 1 mile from long Island Sound - pet friendly
Property grounds

The gardners Cottage 1 mile from long Island Sound - pet friendly

10.0 out of 10, Exceptional, (13)
"The cottage is cozy and clean. It has everything I need. and perfect for me and my dogs. We enjoyed our stay and had a nice winter break. We hope to come back next year. Thank you, Robin!"
The gardners Cottage 1 mile from long Island Sound - pet friendly
Enchanted Waterfront Cottage
Smart TV, fireplace, books

Enchanted Waterfront Cottage

9.0 out of 10, Wonderful, (19)
"The location was perfect. Very comfortable."
Enchanted Waterfront Cottage
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Beach nearby, sun loungers, beach towels

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

9.8 out of 10, Exceptional, (107)
"Cute place, very clean"
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Charming Old Lyme Cottage, Steps to Private Beach!
Coffee/tea maker

Charming Old Lyme Cottage, Steps to Private Beach!

8.6 out of 10, Excellent, (7)
"We booked last minute as we decided to join family staying in Old Lyme. This cottage was just perfect for our needs. My husband and I along with our 19 year old stayed here. Clean, newly remodeled and amenities to meet our needs for a 3 day beach retreat. Simple, but practical. Close to beach and a/c was a treat during the heat wave! ⭐️⭐️⭐️⭐️⭐️"
Charming Old Lyme Cottage, Steps to Private Beach!
Charming Westbrook Cottage, Steps to Private Beach
Microwave, coffee/tea maker, toaster, cookware/dishes/utensils

Charming Westbrook Cottage, Steps to Private Beach

10.0 out of 10, Exceptional, (2)
"Cozy cottage, good location, nice access to the Sound."
Charming Westbrook Cottage, Steps to Private Beach
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Exterior

Cozy cottage near downtown Clinton, Marina & Hammonasset Park

10.0 out of 10, Exceptional, (70)
"We had a magical Christmas here. I fulfilled a lifelong dream to host my family for Christmas Eve Smorgasbord and the jigsaw puzzle had all of the pieces! "
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Waterfront! Charming 4BR Cottage on the Niantic River!
Property grounds

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!
Beachside Twinhome: 2 Private Sides + Sunroom Escape for Friends & Family
Beach nearby, sun loungers

Beachside Twinhome: 2 Private Sides + Sunroom Escape for Friends & Family

10.0 out of 10, Exceptional, (14)
"This rental is so unique with the 2 sides, and was absolutely perfect for our wedding weekend. We had the groom’s friends staying on one side, and my friends staying on the other side. The two sides are connected through the sunroom and the backyard space is great which made bringing the whole group together so easy. The setup was also perfect for me to get ready on my own separate side the day of the wedding so that my now husband wouldn’t see me. The decor and cleanliness of the house were...
Beachside Twinhome: 2 Private Sides + Sunroom Escape for Friends & Family
Beachside Branford- walk t0 Beach, Grill, Fire Pit
Dining

Beachside Branford- walk t0 Beach, Grill, Fire Pit

10.0 out of 10, Exceptional, (3)
"Charming little cottage that was just right for our trip to the CT shoreline."
Beachside Branford- walk t0 Beach, Grill, Fire Pit
Direct waterfront renovated cottage.
TV, books

Direct waterfront renovated cottage.

10.0 out of 10, Exceptional, (71)
"Perfect stay in Madison. Beautiful location. Clean and comfy house. Will be back!"
Direct waterfront renovated cottage.
'Grandma's Cottage' w/ Sunroom: Walk to Beach
Beach nearby

'Grandma's Cottage' w/ Sunroom: Walk to Beach

8.0 out of 10, Very Good, (3)
"Terrific location. 1 block from the beach."
'Grandma's Cottage' w/ Sunroom: Walk to Beach
Beach Cottage
Fridge, microwave, oven, stovetop

Beach Cottage

10.0 out of 10, Exceptional, (3)
"Excellent experience. Great host. Clean, inviting property near beach. Cozy home. Good value. Will stay again. Thank you. "
The price is AED 665
AED 1,513 total
includes taxes & fees
5 May - 6 May
Beach Cottage
Guilford Carriage House at Granite Lodge!
TV

Guilford Carriage House at Granite Lodge!

10.0 out of 10, Exceptional, (9)
"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!
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Miscellaneous

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!
Relax with a beautiful lake view
Outdoor dining

Relax with a beautiful lake view

10.0 out of 10, Exceptional, (19)
"Great location"
Relax with a beautiful lake view
Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook
Beach nearby, sun loungers

Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook

10.0 out of 10, Exceptional, (60)
"Our 2nd time to stay at this cozy little cottage. We always enjoy our time spent here. And we do enjoy the homemade banana bread."
Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook
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

Postcard Cabins Machimoodus
Exterior

Postcard Cabins Machimoodus

2.0 star property
10.0 out of 10, Exceptional, (7)
"We had a GREAT time here!! Just beautiful scenery all around. The cabin was well equipped with everything we needed essentially. I was quite impressed with how comfortable we actually were. There was a temporary power outage but it didn’t last long and management not only delivered more wood to us but also gave it to us for free as we wanted to spend our time outdoors during the outage. Im super happy to have had this experience and would absolutely be doing it again!! Thank you Postcard...
The price is AED 380
AED 585 total
includes taxes & fees
5 May - 6 May
Postcard Cabins Machimoodus
Regency Inn & Suites
1 bedroom, iron/ironing board, WiFi, bed sheets

Regency Inn & Suites

2.0 out of 10, (1)
"Hotel didn’t have out reservation even after we had paid for it - took an hour to check in at midnight - parking lot was full of random activity and people all hours of night and hall ways smelled like weed. Clientele was shady and co within of hotel rooms and surrounding area was dirty, worn out, in need of maintenance and overall place was a dump. Checked out a day early and forfeited a night because place was so disgusting. Expedia needs to remove them from hotel options and do a better job...
The price is AED 279
AED 458 total
includes taxes & fees
22 Apr - 23 Apr
Regency Inn & Suites
Oceanfront Beach House lay in bed and hear the waves, boats , birds
On the beach, sun loungers, beach towels

Oceanfront Beach House lay in bed and hear the waves, boats , birds

10.0 out of 10, Exceptional, (18)
"Very fun location near the beach. Beach is small but really a nice place to be. House worked well for our family of 4. Sun room was very nice."
Oceanfront Beach House lay in bed and hear the waves, boats , birds
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.