Search Cottages in Chester

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 120 Cottages in Chester with updated reviews, rates, and availability.

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Secluded covered entry

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

9.6 out of 10, Exceptional, (204)
"… And it remains a gem! We lucked out w/a foot of snow on Thanksgiving and so kept the fires burning. Just a great, special place."
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
CHARMING 4-bedroom cottage in Weston, Vermont. CLOSE TO SKI RESORTS
Terrace/patio

CHARMING 4-bedroom cottage in Weston, Vermont. CLOSE TO SKI RESORTS

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property is well maintained, clean and has a lot of charm. The backyard offers a stunning view of the mountains, a stream and quaint cottages dotting the landscape. The only surprise was the location on a major roadway. Backing into the driveway can be difficult especially after dark. Otherwise we would highly recommend this home. Andrew the property manager was friendly and helpful. "
CHARMING 4-bedroom cottage in Weston, Vermont. CLOSE TO SKI RESORTS
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

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

8.8 out of 10, Excellent, (43)
"Cabin was perfect for our long weekend. Master bed mattress needs an update, but otherwise everything was fantastic."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Vermont Country Cottage (Near Village)
Exterior

Vermont Country Cottage (Near Village)

9.2 out of 10, Wonderful, (10)
"This cottage reviewed very well online and pictures were very accurate too. It was secluded and far from neighbors, fire house across the street but zero activity the whole weekend. The cottage had the amenities listed. It was neat and tidy, well equipped. Very confortable. Loved the wood stove. We used that and it was wonderful. Check in/out Instructions were easy to follow. The area was beautiful, peacefu and not too far away from groceries, food or beverages. Would definitely go...
The price is SAR 694
SAR 1,485 total
includes taxes & fees
12 Jan - 13 Jan
Vermont Country Cottage (Near Village)
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
Exterior

The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

10.0 out of 10, Exceptional, (7)
"Everything was wonderful from the very beginning… The ease of booking, payment, check-in, property, check out, it was all perfect! The house was in a great neighborhood, very quaint, and just the perfect size for the six of us. Well maintained and clean, had everything we could possibly need. Highly recommend."
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
Charming Cavendish Cottage: All-Season Retreat!
Cavendish Vacation Rental | 3BR | 3BA | 1,500 Sq Ft | Stairs Required

Charming Cavendish Cottage: All-Season Retreat!

2.0 star property
10.0 out of 10, Exceptional, (4)
"Such a wonderful and warm home. Other than condiments the kitchen was well stocked with dishes, cups and small appliances. The back screened in porch was a peaceful retreat for morning coffee and devotions and a great place to wind down at night. The owner was very nice and accommodating. The minute we walked in we were in awe of Rosehill Cottage. We will definitely stay here again if we are in the area."
Charming Cavendish Cottage: All-Season Retreat!
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

9.2 out of 10, Wonderful, (15)
"We loved the cabin and its proximity to the town of Woodstock. Nice to come home at the end of the day. The only issue is the bedrooms are upstairs and the bathroom is downstairs….but we managed. Overall a great stay. "
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

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

9.6 out of 10, Exceptional, (9)
"This lake house is absolutely everything you would expect from a five star rated home. It is a newly renovated lake front home. The house is located about 3 miles north of Ludlow. The property was clean and well maintained. We visited on Columbus Day weekend for our daughter’s wedding. We will return some day in the summer to enjoy the lake. I would recommend this property to my family and friends. Thank you for sharing your home with us during this special time for our family. "
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Home with a spring-fed pond and mountain view.
Terrace/patio

Home with a spring-fed pond and mountain view.

10.0 out of 10, Exceptional, (110)
"Very nice and cozy place to getaway for a few nights! Very close to Manchester and places to eat and things to do. Koi pond was very pretty and we enjoyed feeding them! Loved having coffee on the deck with a view of the mountains, before we went on our adventures! "
Home with a spring-fed pond and mountain view.
This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.
"Great location, comfortable, and spacious. A great home base for a fly-fishing trip to southern Vermont!" - Taylor, *****

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

10.0 out of 10, Exceptional, (25)
"Stayed for 3 nights enjoyed Stowe Mtn only 30 min away. Nice restaurants in area. Very clean practical small house "
This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.
Cozy Historic Hilltop Cottage with Mount Ascutney View
Cottage on the hill

Cozy Historic Hilltop Cottage with Mount Ascutney View

9.6 out of 10, Exceptional, (75)
"This house is exactly as described. It is in a very attractive location with good views and is very private. The house is much larger inside than it appears from the photos but still very cozy and is well equipped. It was spotlessly clean."
Cozy Historic Hilltop Cottage with Mount Ascutney View
Spruce Moose Cottage | Tiny House on 65 private acres

Spruce Moose Cottage | Tiny House on 65 private acres

Spruce Moose Cottage | Tiny House on 65 private acres
Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!
Cottage charm! The Front Cottage at MeadowView

Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!

10.0 out of 10, Exceptional, (24)
"We LOVED our stay at this adorable cottage in Dorset. The cottage is clean, cozy and has everything you need for a comfortable stay. You can’t beat the location - walking distance to Dorset attractions (we loved the bakery) and close to Bromley and Stratton for skiing during the day. My girls were sad to leave. We’re already looking forward to visiting again. Thank you, Nicole!!"
Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!
Cozy farm cottage on gorgeous landscape, quiet but close to s. NH/VT attractions
d4dfddeb-ca93-4c46-84bb-9f6f05aa287b

Cozy farm cottage on gorgeous landscape, quiet but close to s. NH/VT attractions

10.0 out of 10, Exceptional, (6)
"Short time we had there but everything was great would love to stay again for personal trip and see more of the farm "
The price is SAR 916
SAR 1,121 total
includes taxes & fees
10 Feb - 11 Feb
Cozy farm cottage on gorgeous landscape, quiet but close to s. NH/VT attractions
Cozy cottage on the river, minutes from skiing, horse events, and so much more!
Living area

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

10.0 out of 10, Exceptional, (7)
"We loved our stay at the Dark Horse Cottage. It was close to everything we wanted to do. We loved being near the little creek. They thought of everything for amenities. It was perfect for what we needed. "
Cozy cottage on the river, minutes from skiing, horse events, and so much more!
4bdrm Cottage central to year round fun w/fireplace
Exterior

4bdrm Cottage central to year round fun w/fireplace

4bdrm Cottage central to year round fun w/fireplace
Cozy Falls Brook Cabin: Hike & Swim On-site!
Living area

Cozy Falls Brook Cabin: Hike & Swim On-site!

3.0 star property
10.0 out of 10, Exceptional, (1)
"This is exactly how it’s described- perfect cozy spot- babbeling brook to keep you company while sitting on the porch - fire pit for cozy evenings and cabin inside is perfection- cozy cozy cozy!! Matt was the perfect host and readily available- hoping to return!! 15 mins from farmers markets, covered bridges, shops, food, drinks and entertainment ❤️"
Cozy Falls Brook Cabin: Hike & Swim On-site!
'mount Pine' Getaway Near Green Mtn Nat'l Forest!
Outdoor dining

'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!
Idyllic Wallingford Retreat - Near Skiing & Hiking
Dining

Idyllic Wallingford Retreat - Near Skiing & Hiking

3.0 star property
Idyllic Wallingford Retreat - Near Skiing & Hiking
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Terrace/patio

Charming Wilmington Cabin, 8 Mi. to Mt Snow!

3.0 star property
10.0 out of 10, Exceptional, (1)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
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.
Don't see what you're looking for?
See all available properties in Chester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Chester

Long Trail House at Stratton Mountain Resort
Living room

Long Trail House at Stratton Mountain Resort

3.0 star property
8.4 out of 10, Very Good, (72)
"Condo was great, cozy, and clean. Has access to the pool and hot tubs from back porch and has great Mountain View’s. The village had plenty of food, little expensive, but pretty good. Overall great place to stay and enjoy the mountain. "
The price is SAR 1,348
SAR 1,676 total
includes taxes & fees
15 Jan - 16 Jan
Long Trail House at Stratton Mountain Resort
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
Located in the Okemo Mt. Community, a mile to the base lodge

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

9.8 out of 10, Exceptional, (164)
"The property is exactly like the pictures indicate. The house is in a friendly neighborhood outside of town. The house is very comfortable and spacious. The host responds to your messages in timely manner, and, she is very workable. Would definitely stay there again "
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (41)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
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.

Frequently asked questions

Why book your cottage in Chester with Expedia?
We think a getaway should be stress-free, so if you’re seeking cottages in Chester at a competitive rate, Expedia has your back. Keep the budget in check and opt for a low-cost option far away from the city rush, or book a luxury cottage to pamper your favorite people.
How can I find cheap cottages in Chester?
Expedia can help you track down cheap cottages in Chester. To book your dream stay in a couple of quick clicks, simply use our convenient filter tool to refine your search by budget, star rating and amenities.