Search Cottages in Chester

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
10 Oct - 12 Oct
In two months
21 Nov - 23 Nov
In three months
19 Dec - 21 Dec
In four months
16 Jan - 18 Jan

Cottages in Chester

Our top choices for Chester cottages

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

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

9.6 out of 10, Exceptional, (233)
"Extremely cozy. Would highly recommend staying here."
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
Exterior

The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

10.0 out of 10, Exceptional, (17)
"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
Charming pet-friendly, Meadow View Cottage in heart of historic Dorset VT!
Exterior

Charming pet-friendly, Meadow View Cottage in heart of historic Dorset VT!

10.0 out of 10, Exceptional, (28)
"Loved Dorset and this house was great. Very clean and living area was nice to spend time with family. Also close to skiing which we took advantage of"
Charming pet-friendly, Meadow View Cottage in heart of historic Dorset VT!
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, (66)
"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
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Exterior

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

8.4 out of 10, Very Good, (58)
"Great location and super cute"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Vermont Country Cottage (Near Village)
Exterior

Vermont Country Cottage (Near Village)

9.4 out of 10, Exceptional, (14)
"Cute place. Enjoyed our stay. "
Vermont Country Cottage (Near Village)
Woodstock Village Carriage House
Exterior

Woodstock Village Carriage House

9.8 out of 10, Exceptional, (98)
"A very pleasant experience all around. The house is great and the town is charming. Thank you! "
Woodstock Village Carriage House
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
House (2 Bedrooms) | Interior

Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!

3.0 star property
10.0 out of 10, Exceptional, (1)
"The property was lovely, peaceful, and quiet, surrounded by trees on a quiet country drive. It was the perfect weekend getaway and we really enjoyed sitting on the porch and out under the string lights, watching the sun go down through the trees. The house itself is lovely, cozy, and comfortable. Our hosts were very sweet, everything was very thoughtfully laid out and clean and easy to access. We also loved meeting the goats, Ozzy and Coco, and the chickens! This was such a pleasant stay, I...
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
Cozy Historic Hilltop Cottage with Mount Ascutney View
Exterior

Cozy Historic Hilltop Cottage with Mount Ascutney View

9.6 out of 10, Exceptional, (79)
"Great location for our vacation. Owner was bery quick to respond to questionsz"
Cozy Historic Hilltop Cottage with Mount Ascutney View
Cozy cottage on the river, minutes from skiing, horse events, and so much more!
Exterior

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

10.0 out of 10, Exceptional, (9)
"very good cozy location. enjoyed the privacy during our stay."
Cozy cottage on the river, minutes from skiing, horse events, and so much more!
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)
"The property was as described, very clean, updated with a nice view. WeHad fun exploring the area.We enjoyed the fireplace while relaxing after hiking and exploring."
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Home with a spring-fed pond and mountain view.
Exterior

Home with a spring-fed pond and mountain view.

10.0 out of 10, Exceptional, (119)
"This house was fantastic. We didn’t have the best weather this Memorial Day weekend but the house, pond and view made up for it. Jeremy stocked the house with everything we could possibly need including fresh eggs from the resident chickens, bacon, snacks and so much more. It was quiet and the bed was super comfortable. Our dog enjoyed watching the beautiful fish in the pond and visiting the chickens. We can’t wait to return!"
Home with a spring-fed pond and mountain view.
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
House (4 Bedrooms) | Interior

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!
Cottage (2 Bedrooms) | Interior

Rustic Marlboro Cottage: 4 Mi to Lake Raponda!

3.0 star property
Rustic Marlboro Cottage: 4 Mi to Lake Raponda!
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.
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!
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
House (3 Bedrooms) | 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
House (4 Bedrooms) | 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
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, (8)
"Great, clean, charming cottage. The hosts are amazing and communicated every detail, very hospitable. Highly recommend. "
The price is SAR 1,346
SAR 1,648 total
includes taxes & fees
6 Oct - 7 Oct
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
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

Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"Good location and value"
Alan 1-night trip
Posted 4 days ago
Hampton Inn Brattleboro

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.