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

Search Chester Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

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, (67 reviews)
"Cozy vrbo with a great location to the beach, outlets shops and excellent restaurants!"
United States
Marcy C.
$222 nightly
The price is $253
Nov 19 - Nov 20
Total with taxes and fees
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, (32 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
$300 nightly
The price is $341
Nov 15 - Nov 16
Total with taxes and fees
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.
$253 nightly
The price is $288
Nov 16 - Nov 17
Total with taxes and fees
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
A two-story house with a porch, multiple windows, and a front door.

4. 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.
$496 nightly
The price is $565
Nov 14 - Nov 15
Total with taxes and fees
Adorable Cottage with Cottage porch, walk to water & town
A living room with stone walls, a fireplace, and a seating area with a sofa and armchairs.

5. Westbrook Getaway-Near Beaches, Train & Shoreline

Westbrook Getaway-Near Beaches, Train & Shoreline
Westbrook Center
$351 nightly
The price is $401
Dec 2 - Dec 3
Total with taxes and fees
Westbrook Getaway-Near Beaches, Train & Shoreline
A small white house with black shutters, a porch, and a red barn in the background.

6. The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, Exceptional, (14 reviews)
"Love love love this place. A very unique setting on a little farm and the cabin was great. Everything ya need. A gorgeous setting. Tom, the owner is great. Will. Be. Back."
United States
Paul
$134 nightly
The price is $152
Nov 15 - Nov 16
Total with taxes and fees
The Tiny Cottage & Mini Farm
A lakeside house with a deck, surrounded by trees and a dock.

7. Waterfront! Brand New Cozy Cottage in Old Lyme, CT

Waterfront! Brand New Cozy Cottage in Old Lyme, CT
Old Lyme
10.0 out of 10, Exceptional, (7 reviews)
"Was a great stay very cute property and quiet neighborhood. Stores nearby and easy to access. Friendly and helpful host."
United States
Jessica H.
$403 nightly
The price is $459
Nov 20 - Nov 21
Total with taxes and fees
Waterfront! Brand New Cozy Cottage in Old Lyme, CT
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.

8. 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
$273 nightly
The price is $310
Nov 15 - Nov 16
Total with taxes and fees
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.

9. 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, (36 reviews)
"The stay was great and the host was more than kind and very helpful! "
United States
Jenna K.
$302 nightly
The price is $344
Dec 9 - Dec 10
Total with taxes and fees
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.

10. 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
$340 nightly
The price is $387
Dec 14 - Dec 15
Total with taxes and fees
115 Rose Cottage with 2 bedroom walk to Groton Bay
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area

Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area

10/10 Excellent
"The room was clean, and property was clean. The breakfast was good. The area felt safe and it was quiet"
Alece 1-night trip
Posted 5 hours ago
Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area

Find out more about Chester

Chester Cottages information

Number of reviews
106
Accommodation
135 Cottages
Lowest Price
$152
Highest Price
$565

Frequently asked questions

How much do cottages in Chester cost?
You can expect to pay between $152 and $565 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 135 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.
What is there to do in Chester near my cottage?
If you're eager to discover the best of Chester, find your way to Norma Terris Theater. It's a winner with locals and tourists alike.

Explore a world of travel with Expedia