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Featured Cottages in Chester

Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
Interior

Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!

3.0 star property
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes!
Interior

Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great place "
Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes!
Near Skiing & Hiking: Quiet Home in West Wardsboro
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Near Skiing & Hiking: Quiet Home in West Wardsboro

3.0 star property
Near Skiing & Hiking: Quiet Home in West Wardsboro
Rustic Marlboro Cottage: 4 Mi to Lake Raponda!
Interior

Rustic Marlboro Cottage: 4 Mi to Lake Raponda!

3.0 star property
Rustic Marlboro Cottage: 4 Mi to Lake Raponda!
Luxury Vermont Vacation Rental: Private Hot Tub!
Interior

Luxury Vermont Vacation Rental: Private Hot Tub!

3.0 star property
Luxury Vermont Vacation Rental: Private Hot Tub!
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
Front of property

Wilmington Home on 18 Acres ~ 9 Mi to Skiing!

3.0 star property
10.0 out of 10, Exceptional, (1)
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
West Dover Vacation Rental w/ Hot Tub Near Mt Snow
Interior

West Dover Vacation Rental w/ Hot Tub Near Mt Snow

3.0 star property
West Dover Vacation Rental w/ Hot Tub Near Mt Snow
Wilmington Retreat Near Trails, Skiing & Festivals
Interior

Wilmington Retreat Near Trails, Skiing & Festivals

3.0 star property
10.0 out of 10, Exceptional, (2)
"Great location and awesome house. Owners were easy to communicate with. "
Wilmington Retreat Near Trails, Skiing & Festivals
Peaceful Marlboro Vacation Rental w/ Sauna & Yard!
Interior

Peaceful Marlboro Vacation Rental w/ Sauna & Yard!

3.0 star property
Peaceful Marlboro Vacation Rental w/ Sauna & Yard!
'mount Pine' Getaway Near Green Mtn Nat'l Forest!
Interior

'mount Pine' Getaway Near Green Mtn Nat'l Forest!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Amazing place! Super clean and cozy, and host was extremely nice and communicative. Highly recommend."
'mount Pine' Getaway Near Green Mtn Nat'l Forest!
Londonderry Chalet w/ Deck, Fire Pit & Views!
Front of property

Londonderry Chalet w/ Deck, Fire Pit & Views!

3.0 star property
Londonderry Chalet w/ Deck, Fire Pit & Views!
Charming Putney Home: Porch, Grill & Hiking Trails
Interior

Charming Putney Home: Porch, Grill & Hiking Trails

3.0 star property
Charming Putney Home: Porch, Grill & Hiking Trails
Londonderry Retreat ~ 3 Mi to Lowell Lake!
Interior

Londonderry Retreat ~ 3 Mi to Lowell Lake!

3.0 star property
Londonderry Retreat ~ 3 Mi to Lowell Lake!
Lakefront Paradise Near Okemo & Killington
Interior

Lakefront Paradise Near Okemo & Killington

3.0 star property
Lakefront Paradise Near Okemo & Killington
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
Front of property

Chester Farmhouse on 100 Acres, 15 Min to Okemo!

3.0 star property
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
4 Mi to Mount Snow: West Dover Cabin w/ Game Room
Interior

4 Mi to Mount Snow: West Dover Cabin w/ Game Room

3.0 star property
4 Mi to Mount Snow: West Dover Cabin w/ Game Room
Historic New Hampshire Home: 1 Mi to Boat Launch
Interior

Historic New Hampshire Home: 1 Mi to Boat Launch

3.0 star property
Historic New Hampshire Home: 1 Mi to Boat Launch
18 Mi to Skiing: Colorful Home in Springfield!
Interior

18 Mi to Skiing: Colorful Home in Springfield!

3.0 star property
18 Mi to Skiing: Colorful Home in Springfield!
Picture-perfect Vermont Mtn Cabin w/ Hot Tub!
Interior

Picture-perfect Vermont Mtn Cabin w/ Hot Tub!

3.0 star property
Picture-perfect Vermont Mtn Cabin w/ Hot Tub!
Spacious Dover Home w/ Sauna < 5 Miles to Ski!
Outdoor dining

Spacious Dover Home w/ Sauna < 5 Miles to Ski!

3.0 star property
10.0 out of 10, Exceptional, (1)
"we enjoyed all of the space and the location a short distance from the resort. very comfortable stay for a group of five."
Spacious Dover Home w/ Sauna < 5 Miles to Ski!
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

Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"Staff was very friendly and professional. Bed was very comfortable! Breakfast was good!"
Christine 1-night trip
Posted 5 days ago
Hampton Inn Brattleboro

Find out more about Chester

Find out more about Chester

Chester Cottages information

Number of reviews
2
Accommodation
127 Cottages
Lowest Price
Highest Price

Frequently asked questions

Why book your cottage in Chester with Expedia?
We think that traveling should be a walk in the park, so if you're on the lookout for cottages in Chester at a competitive price, Expedia has you covered. Stick to the budget and choose a cheap option far from the hustle and bustle, or splurge on an upscale cottage to pamper your loved ones.
How can I find cheap cottages in Chester?
Expedia can help you look for cheap cottages in Chester. To reserve a superb stay in a few quick clicks, try out our handy filter tool to refine your search by amenities, star rating and budget.
What is there to do in Chester near my cottage?
Once you've unpacked your suitcases, venture out and discover the incredible things Chester has on offer. DaVallia Art & Accents is a top attraction to add to your must-do list.

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