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Compare 110 Cottages in Chester with updated reviews, rates, and availability.

115 Rose Cottage with 2 bedroom walk to Groton Bay
Bedroom 1
115 Rose Cottage with 2 bedroom walk to Groton Bay
9.2 out of 10, Wonderful, (7)
"Very nice little place. Quite, clean and only minutes from Mystic and downtown New London."
The price is SAR 608
SAR 1,507 total
includes taxes & fees
21 Oct - 22 Oct
115 Rose Cottage with 2 bedroom walk to Groton Bay
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Welcome to our cute getaway
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
10.0 out of 10, Exceptional, (67)
"Perfect and cozy home base for visiting with family!"
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Luxury Cottage walking distance to Saybrook Point Marina
Exterior
Luxury Cottage walking distance to Saybrook Point Marina
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
Beach Bungalow, large porch, 1/2 mile to the water.
Exterior
Beach Bungalow, large porch, 1/2 mile to the water.
10.0 out of 10, Exceptional, (2)
"We stayed 10 days. Communication with the owners was excellent. The house was very clean and owners even stopped by after a few days and dropped off more towels. The porch was nice to sit and have a drink in the evening. The view from porch is a house across the street (no water view) the bedrooms have air conditioning. None on first floor but plenty of windows and screen door to allow airflow. They also have a grill which was a nice option that we used. Our favorite place to visit was a coffee...
The price is SAR 746
SAR 1,447 total
includes taxes & fees
29 Sep - 30 Sep
Beach Bungalow, large porch, 1/2 mile to the water.
Private Guest House w/ Deck + Spectacular Views!
Montville Vacation Rental | 1BR | 1BA | 625 Sq Ft | Stairs Required to Enter
Private Guest House w/ Deck + Spectacular Views!
10.0 out of 10, Exceptional, (19)
"This is incredible find and Al, the host, could not have been more hospitable. The rental is so close to downtown New London and Niantic and the highway that it was easy to get to and from all major necessities and recreation. We loved the design of the guest house and had everything we needed (air fryer added from the pictures only). The grounds were meticulously kept and the pool was inviting and warm! The view was unparalleled, especially when considering how close to a city we were. Looks...
Private Guest House w/ Deck + Spectacular Views!
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Marina
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
10.0 out of 10, Exceptional, (99)
"My family and I had a great stay at this adorable beach house! It had plenty of room for our family of 6. The private beach was just a short walk around the corner! "
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Waterfront! Charming 4BR Cottage on the Niantic River!
Exterior
Waterfront! Charming 4BR Cottage on the Niantic River!
9.6 out of 10, Exceptional, (58)
"We enjoyed this lovely old home and had a lot of fun kayaking and seeing the sights in the area. Amy was a wonderful host."
Waterfront! Charming 4BR Cottage on the Niantic River!
Waterfront Cottage in Branford
Exterior
Waterfront Cottage in Branford
10.0 out of 10, Exceptional, (83)
"We enjoyed our 2nd time at this house. Well-appointed and lots of space for our family to connect. Can’t beat the view!"
Waterfront Cottage in Branford
Guilford Carriage House at Granite Lodge!
Guilford Vacation Rental | 1BR | 1BA | Step-Free Access via Side Door
Guilford Carriage House at Granite Lodge!
10.0 out of 10, Exceptional, (7)
"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!
Go Jump in the Lake!
Go Jump in the Lake!
10.0 out of 10, Exceptional, (133)
"The house was clean and neat. We had everything we needed for a great stay. The"
Go Jump in the Lake!
The gardners Cottage 1 mile from long Island Sound - pet friendly
Exterior
The gardners Cottage 1 mile from long Island Sound - pet friendly
10.0 out of 10, Exceptional, (12)
"We had a marvelous one week stay at Robin's cottage. Our host was very friendly and helpful. Location is very convenient and close to many points of interest, 5 Minutes to the beach, half an hour to New Haven or Gillette Castle. Thanks so very much"
The gardners Cottage 1 mile from long Island Sound - pet friendly
Charming Old Saybrook Cottage < 1 Mi to Beach
Old Saybrook Vacation Rental | 4BR | 2BA | Steps Required | 1,400 Sq Ft
Charming Old Saybrook Cottage < 1 Mi to Beach
10.0 out of 10, Exceptional, (20)
"Spacious, in a great location, this cottage was perfect for our family. Clean and good space to be together in both the family room and finished basement."
Charming Old Saybrook Cottage < 1 Mi to Beach
Beach access Cozy Cottage
Interior
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
Charming Deep River Vacation Rental on Star Lake!
Deep River Vacation Rental | 2BR | 1BA | Step Required | 618 Sq Ft
Charming Deep River Vacation Rental on Star Lake!
8.8 out of 10, Excellent, (3)
"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!
A cozy cottage with a beautiful deck - swim, hike and play!
Living area
A cozy cottage with a beautiful deck - swim, hike and play!
10.0 out of 10, Exceptional, (6)
"quiet,comfortable, exactly as described"
A cozy cottage with a beautiful deck - swim, hike and play!
Beach Cottage
Aerial view
Beach Cottage
Beach Cottage
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
10.0 out of 10, Exceptional, (12)
"We truly enjoyed this lovely spot while dropping our son off at Wesleyan University. It was a perfect little spot to relax and enjoy the water and beautiful sunsets. "
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
70 Year old cottage on 2.8 acres, stunning views and sunsets
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
The Bay Cottage · Rocky Neck Park, Beach & Niantic
The Bay Cottage · Rocky Neck Park, Beach & Niantic
9.0 out of 10, Wonderful, (10)
"Met our needs nicely"
The price is SAR 886
SAR 1,852 total
includes taxes & fees
30 Sep - 1 Oct
The Bay Cottage · Rocky Neck Park, Beach & Niantic
"Salt 'n' Lyme" - Walk to everything !
Property grounds
"Salt 'n' Lyme" - Walk to everything !
9.2 out of 10, Wonderful, (27)
"This was our second year staying at this sweet little cottage. It is everything we need - great location, clean, and allows our pups to join us."
"Salt 'n' Lyme" - Walk to everything !
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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
Living area
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
10.0 out of 10, Exceptional, (22)
"The villa was so perfect for an overnight stay. It was clean, well stocked with everything you need, down to coffee and creamer. The grounds are pretty, with the fountains and little bridges. I would definitely stay here again."
The price is SAR 656
SAR 1,282 total
includes taxes & fees
29 Sep - 30 Sep
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Property grounds
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
9.2 out of 10, Wonderful, (80)
"We enjoyed our long weekend stay at the Count House. Its location was perfect ... easy beach access, close to the highway, etc. Everything we needed was supplied for us to enjoy the beach, cook our meals, or play games. There was only one full-size kayak with paddle and the paddle board paddle was broken (but we used it by kneeling on the board!). We would definitely return."
The price is SAR 563
SAR 1,618 total
includes taxes & fees
29 Sep - 30 Sep
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Private Guest House w/ Deck + Spectacular Views!
Montville Vacation Rental | 1BR | 1BA | 625 Sq Ft | Stairs Required to Enter
Private Guest House w/ Deck + Spectacular Views!
10.0 out of 10, Exceptional, (19)
"This is incredible find and Al, the host, could not have been more hospitable. The rental is so close to downtown New London and Niantic and the highway that it was easy to get to and from all major necessities and recreation. We loved the design of the guest house and had everything we needed (air fryer added from the pictures only). The grounds were meticulously kept and the pool was inviting and warm! The view was unparalleled, especially when considering how close to a city we were. Looks...
Private Guest House w/ Deck + Spectacular Views!
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 SAR344 and SAR437 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 110 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.