A calm river with boats, wooden docks, and buildings along the shore.

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Chester cottages

A small single-story house with a front porch, a potted plant, and two Adirondack chairs.

1. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.8 out of 10, Exceptional, (66 reviews)
"We enjoyed our stay"
United States
JM B.
The price is AED 597
AED 1,043 total
includes taxes & fees
2 Nov - 3 Nov
1-bedroom cottage with Grove Beach 🏖️ access.
A white cottage with a front door, a garage, and a small porch with a potted plant.

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

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
9.8 out of 10, Exceptional, (30 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is AED 579
AED 1,100 total
includes taxes & fees
27 Oct - 28 Oct
The gardners Cottage 1 mile from long Island Sound - pet friendly
A two-story house with a porch, a mailbox, and a lawn.

3. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Madison
9.4 out of 10, Exceptional, (3 reviews)
"Cozy cottage was perfect for our long weekend in Madison!"
United States
Samantha D.
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
A living room with stone walls, a fireplace, and a seating area with a sofa and armchairs.

4. Westbrook Getaway-Near Beaches, Train & Shoreline

Westbrook Getaway-Near Beaches, Train & Shoreline
Westbrook Center
The price is AED 902
AED 1,287 total
includes taxes & fees
27 Oct - 28 Oct
Westbrook Getaway-Near Beaches, Train & Shoreline
A two-story house with a porch, multiple windows, and a front door.

5. Adorable Cottage with Cottage porch, walk to water & town

Adorable Cottage with Cottage porch, walk to water & town
Westbrook Center
9.0 out of 10, Wonderful, (8 reviews)
"Very clean and comfortable"
United States
Francine F.
The price is AED 829
AED 2,005 total
includes taxes & fees
27 Oct - 28 Oct
Adorable Cottage with Cottage porch, walk to water & town
A wooden deck with potted plants and a view of a lush landscape.

6. Private Guest House w/ Deck + Spectacular Views!

Private Guest House w/ Deck + Spectacular Views!
3.0 star property
Montville
10.0 out of 10, Exceptional, (3 reviews)
"The pool was amazing, the host was great, very accessible and the property was prisine. The views alone made us immediately want to come back. Very clean and well stocked. "
United States
agata
Private Guest House w/ Deck + Spectacular Views!
A small white house with black shutters, a porch, and a red barn in the background.

7. The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, Exceptional, (13 reviews)
"I'll stay again if in the area. "
United States
Jeffrey H.
The price is AED 380
AED 511 total
includes taxes & fees
29 Oct - 30 Oct
The Tiny Cottage & Mini Farm
A wooden deck with potted plants and a view of a lush landscape.

8. Private Guest House w/ Deck + Spectacular Views!

Private Guest House w/ Deck + Spectacular Views!
Montville
10.0 out of 10, Exceptional, (43 reviews)
"Home away from home with one major key asset: Allan, the host is a gem ; extremely welcoming, discreet, hands-on, friendly - very smart so will adapt to the guests. keeps the place a perfect spot to spend few days with family or friends away from the action of the city but very close by car. You are right in the middle of nature (great if you love it), with a wonderful view, an amazingly private large pool (never seen on any rentals before) and a comfortable guesthouse with all the basics you...
United States
pierre g.
Private Guest House w/ Deck + Spectacular Views!
A dining area with a round wooden table surrounded by six white chairs with dark cushions. A potted plant with green foliage and pink flowers is placed in the center.

9. Privet Farm cottage with AC and Deck in charming Salem Connecticut

Privet Farm cottage with AC and Deck in charming Salem Connecticut
Salem
9.0 out of 10, Wonderful, (4 reviews)
"The place was perfect! So much bigger and nicer in person!!!!! Well appointed very cozy! Clean!!!!! Very pet friendly! Great shower!"
United States
Kellie
The price is AED 716
AED 1,284 total
includes taxes & fees
9 Nov - 10 Nov
Privet Farm cottage with AC and Deck in charming Salem Connecticut
A small, single-story house with a white porch and a wooden front door.

10. Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Waterford
10.0 out of 10, Exceptional, (35 reviews)
"The stay was great and the host was more than kind and very helpful! "
United States
Jenna K.
The price is AED 753
AED 1,450 total
includes taxes & fees
15 Nov - 16 Nov
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
A small white house with a green door, two wicker chairs with red cushions, and a welcome mat.

11. 115 Rose Cottage with 2 bedroom walk to Groton Bay

115 Rose Cottage with 2 bedroom walk to Groton Bay
Groton
8.8 out of 10, Excellent, (9 reviews)
"We had a great time and the property provided everything we needed. Thank you!"
United States
Meredith
The price is AED 606
AED 1,496 total
includes taxes & fees
9 Nov - 10 Nov
115 Rose Cottage with 2 bedroom walk to Groton Bay
A covered outdoor area with a stone patio, a grill, and Adirondack chairs overlooking a forested landscape.

12. Montville Retreat Near Mohegan Sun: 2-home Bundle!

Montville Retreat Near Mohegan Sun: 2-home Bundle!
3.0 star property
Montville
Montville Retreat Near Mohegan Sun: 2-home Bundle!
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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Top Chester Hotel Reviews

Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area

10/10 Excellent
"Great, clean, free shuttle"
Kimberly 1-night trip
Posted 1 hour ago
Hyatt Place Uncasville - Casino Area

Frequently asked questions

How much do cottages in Chester cost?
You can expect to pay between AED 511 and AED 2,005 per night for cottages in Chester. No matter your budget, an epic stay is only a click or two away on Expedia. 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?
Enjoy reconnecting with nature in one of the 136 cottages located in Chester. To help you find your ideal place, use our handy filter tool to search for must-have amenities.
Why book your cottage in Chester with Expedia?
We think that a vacay should be simple, so if you're after cottages in Chester at a great price, Expedia delivers. Stick to the budget and go for a wallet-friendly option far from the hustle and bustle, or book a luxury cottage to spoil your favorite people.
How can I find cheap cottages in Chester?
With Expedia's filter tool, scoring cheap cottages in Chester has never been simpler. To view properties that'll make your bank balance smile, refine your search by amenities, budget and star rating.