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Compare 115 Cottages in Chester with updated reviews, rates, and availability.

Waterfront Cottage in Branford

10.0 out of 10, Exceptional, (90)
"House is beautiful and the view even better. On the waters edge and very quiet grandkids were occupied and very happy "
Waterfront Cottage in Branford

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

9.8 out of 10, Exceptional, (107)
"Cute place, very clean"
The price is AED 793
AED 1,850 total
includes taxes & fees
17 Feb - 18 Feb
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

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

A beach cottage gem...

10.0 out of 10, Exceptional, (62)
"“Driftwood cottage” was everything we were looking for when planning our visit. Clean, well appointed, comfortable and on the beach. This place is truly a gem. Hated to leave!"
A beach cottage gem...

Go Jump in the Lake!

10.0 out of 10, Exceptional, (138)
"Spent Christmas at the cottage with my family and we had an amazing time!! I highly recommend! Beautiful place, beautiful area! The host was fantastic and very responsive! 10/10! "
Go Jump in the Lake!

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

Updated cottage "Beriozka" on Cedar Lake

10.0 out of 10, Exceptional, (4)
"Pleasant and fully equipped, walking distance to a small lake with a beach good for watching the sunrise and reading."
Updated cottage "Beriozka" on Cedar Lake

A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve

10.0 out of 10, Exceptional, (2)
"This was an amazing place to stay. Beautiful property and EXCELLENT hosts! Thank you!"
A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve

Newly Remodeled 2 Bedroom Cottage On The Beach. The Kaitlyn Cottage

9.8 out of 10, Exceptional, (26)
"Beautiful place, clean , enjoyable beachside"
Newly Remodeled 2 Bedroom Cottage On The Beach. The Kaitlyn Cottage

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

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!

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

1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets

9.0 out of 10, Wonderful, (22)
"Spent a weekend in this cottage while attending an event for my daughter. Very cozy and comfortable. Host was great, with excellent communication. Renovations are taking place in adjacent units, however it did not impact my stay. Highly recommend. "
The price is AED 345
AED 639 total
includes taxes & fees
17 Feb - 18 Feb
1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets

Driftwood Cottage @ 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."
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

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

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!

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

Enchanted Waterfront Cottage

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

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

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.
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

2.0 star property
10.0 out of 10, Exceptional, (4)
"Loved how tranquil this site is. Was great to disconnect in nature. "
The price is AED 331
AED 380 total
includes taxes & fees
4 Mar - 5 Mar
Postcard Cabins Machimoodus

Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premises

10.0 out of 10, Exceptional, (13)
"We were thoroughly pleased with our stay. This villa is homey, inviting and all of your needs and extra perks are covered.Kellie is a lovely host she answers all of your questions promptly. She and her husband love this property and it is reflective when you enter the villa.We will be back sooner than later."
The price is AED 496
AED 990 total
includes taxes & fees
25 Feb - 26 Feb
Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premises

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

10.0 out of 10, Exceptional, (31)
"The perfect place to relax and get ready for a night out after an amazing day at the spa. Wish we had more time to enjoy the fireplace and rhe balcony. Nice open space wirh plenty of room and very well equipped, comfortable. We loved it!"
The price is AED 643
AED 1,259 total
includes taxes & fees
17 Feb - 18 Feb
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
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 345 and AED 793 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 115 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.