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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Cottages in Chester

Our top choices for Chester cottages

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Dining

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

9.6 out of 10, Exceptional, (227)
"We had an incredible time staying at the cottage and can't wait to visit again sometime! From hiking, sitting on the porch drinking coffee, cooking while listening to music, and enjoying time on the pond, everything about our stay was perfect. "
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Woodstock Village Carriage House
Exterior

Woodstock Village Carriage House

9.6 out of 10, Exceptional, (95)
"Location was great!!"
Woodstock Village Carriage House
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Exterior

Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

9.8 out of 10, Exceptional, (17)
"We loved the house and especially the location. The views are beautiful and the proximity to town, the mountain and parks make it a fantastic spot to stay."
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Outdoor dining

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

8.6 out of 10, Excellent, (56)
"really enjoyed our stay. Place would be much better if there was a microwave."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
Exterior

The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

10.0 out of 10, Exceptional, (13)
"We very much enjoyed our stay in this historic, architecturally significant home. We would definitely stay here again."
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
Cozy cottage on the river, minutes from skiing, horse events, and so much more!
Fridge, microwave, oven, stovetop

Cozy cottage on the river, minutes from skiing, horse events, and so much more!

10.0 out of 10, Exceptional, (7)
"very good cozy location. enjoyed the privacy during our stay."
Cozy cottage on the river, minutes from skiing, horse events, and so much more!
Home with a spring-fed pond and mountain view.
Pool

Home with a spring-fed pond and mountain view.

10.0 out of 10, Exceptional, (118)
"Cute cottage with a lot of charm. The kiddos loved the concept of staying next to a pond. Convenient location to Manchester center and also to Bromley. Jeremy was quick to respond to all to all pf our questions."
Home with a spring-fed pond and mountain view.
Vermont Country Cottage (Near Village)
Exterior

Vermont Country Cottage (Near Village)

9.4 out of 10, Exceptional, (13)
"Cute place. Enjoyed our stay. "
Vermont Country Cottage (Near Village)
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!
Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes!
House (3 Bedrooms) | 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
Interior

Near Skiing & Hiking: Quiet Home in West Wardsboro

3.0 star property
Near Skiing & Hiking: Quiet Home in West Wardsboro
This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.
Exterior

This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.

10.0 out of 10, Exceptional, (28)
"This was a great location… close to town but also close to skiing, hiking and skating."
This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.
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!
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
TV, books

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

10.0 out of 10, Exceptional, (7)
"Great, clean, charming cottage. The hosts are amazing and communicated every detail, very hospitable. Highly recommend. "
The price is AU$431
includes taxes & fees
24 Aug - 25 Aug
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow
Exterior

Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow

9.6 out of 10, Exceptional, (65)
"We enjoyed our stay in this cozy cabin on the ridge. The owners have great taste and they have thought of everything to make the stay pleasant. "
Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
House (3 Bedrooms) | Private kitchen

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!
'mount Pine' Getaway Near Green Mtn Nat'l Forest!
House (3 Bedrooms) | 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!
Wilmington Retreat Near Trails, Skiing & Festivals
House (3 Bedrooms) | Interior

Wilmington Retreat Near Trails, Skiing & Festivals

3.0 star property
10.0 out of 10, Exceptional, (1)
"Would definitely recommend! House had an everything we would need. So comfy and cozy! "
Wilmington Retreat Near Trails, Skiing & Festivals
Peaceful Marlboro Vacation Rental w/ Sauna & Yard!
House (2 Bedrooms) | Interior

Peaceful Marlboro Vacation Rental w/ Sauna & Yard!

3.0 star property
Peaceful Marlboro Vacation Rental w/ Sauna & Yard!
Luxury Vermont Vacation Rental: Private Hot Tub!
House (4 Bedrooms) | Interior

Luxury Vermont Vacation Rental: Private Hot Tub!

3.0 star property
Luxury Vermont Vacation Rental: Private Hot Tub!
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

The Shire Woodstock

The Shire Woodstock

10/10 Excellent
"Forth time at The Shire, everything was wonderful!! "
Judith 1-night trip
Posted 1 day ago
The Shire Woodstock

Frequently asked questions

What is there to do in Chester near my cottage?
Once you've unpacked your suitcases, get out and explore the fantastic things Chester has for you to experience. DaVallia Art & Accents is a top attraction to add to your travel itinerary.