A covered wooden bridge over a river, surrounded by rocky terrain and greenery.

Villas in Chester

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27
No exact matches found, but these alternatives could be just right

Recommended hotels in Chester

A two-story building with a central entrance, a balcony with railings, and a sign indicating it is a lodging and fine dining establishment.

1. Fullerton Inn

Fullerton Inn
2.5 star property
Chester Depot
8.2 out of 10, Very Good, (451 reviews)
"Quaint that never gets old when staying a night."
United States
Kirsty
$125 nightly
The price is $136
Sep 8 - Sep 9
Total with taxes and fees
Fullerton Inn
A red barn with a white door and shutters, surrounded by a garden with various plants and flowers.

2. Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (123 reviews)
"We had a lovely stay at Stone Hearth Inn! Very quaint place and comfortable, clean accommodations. Beautiful grounds around the property with outside seating to enjoy the fresh air. The dinner we had at the attached “Eatery” was awesome!!! So was the amazingly delicious included breakfast. Vickie was so welcoming and kind. We can’t say enough good things! Highly recommend"
United States
Kathleen
$205 nightly
The price is $223
Sep 14 - Sep 15
Total with taxes and fees
Stone Hearth Inn and Eatery
A two-story house with a porch, a small garden, and a well-maintained lawn.

3. Historic 150-year-old farmhouse, Jacuzzi included

Historic 150-year-old farmhouse, Jacuzzi included
Chester Depot
9.6 out of 10, Exceptional, (20 reviews)
"Great stay! Colin was very friendly and attentive. House was very spacious and the hot tub was a great addition! Would definitely stay again! "
United States
Ryan K.
$377 nightly
The price is $422
Sep 8 - Sep 9
Total with taxes and fees
Historic 150-year-old farmhouse, Jacuzzi included
A two-story house with a front porch, a driveway, and autumn foliage.

4. Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes
Chester Depot
9.4 out of 10, Exceptional, (22 reviews)
"Beautiful classic farmhouse in lovely neighbourhood."
United States
Kimberly B.
$377 nightly
The price is $422
Sep 8 - Sep 9
Total with taxes and fees
Charming Chester Farmhouse near Near VT Slopes

5. Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
Andover
10.0 out of 10, Exceptional, (1 review)
"Very nice stay. Owners were very gracious. House was clean & comfortable."
United States
Lorraine C.
$571 nightly
The price is $640
Sep 6 - Sep 7
Total with taxes and fees
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
A two-story house with a deck, surrounded by dense forest.

6. 4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
Chester
10.0 out of 10, Exceptional, (4 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
$899 nightly
The price is $1,007
Sep 12 - Sep 13
Total with taxes and fees
4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
A triangular wooden structure in a grassy field with a path leading to it.

7. Otherland Hotel

Otherland Hotel
2.5 star property
Newfane
9.6 out of 10, Exceptional, (217 reviews)
"Clean, modern, and peaceful."
Canada
Omar
$157 nightly
The price is $171
Sep 7 - Sep 8
Total with taxes and fees
Otherland Hotel
A hotel with a covered entrance, stone facade, and a sign indicating it is part of the Best Western chain.

8. Best Western Springfield Hotel

Best Western Springfield Hotel
2.5 star property
Springfield
8.8 out of 10, Excellent, (875 reviews)
"Clean Room, Convenient Location"
United States
Gerry
$161 nightly
The price is $177
Sep 13 - Sep 14
Total with taxes and fees
Best Western Springfield Hotel
A large two-story house with a front porch and a well-maintained lawn.

9. The Landgrove

The Landgrove
3.5 star property
Londonderry
8.4 out of 10, Very Good, (6 reviews)
"Tammy, the assistant inn keeper and restaurant manager was fantastic. She was attentive to every need. The restaurant staff was phenomenal as well highly recommend, it’s a little hidden gem off the beaten path. I will definitely return. Had a fabulous time."
United States
Andrea
$159 nightly
The price is $174
Sep 7 - Sep 8
Total with taxes and fees
The Landgrove
A motel with a central staircase, multiple rooms, and a parking lot.

10. Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT
2.5 star property
Brattleboro
6.0 out of 10, (801 reviews)
"Good for a one-night stay. The room was comfortable enough for a quick stop while traveling. A big bonus is that they are very dog friendly, which made things much easier since we were traveling with our dogs. I would stay again if I needed a convenient place for the night."
United States
Jessica
$84 nightly
The price is $92
Sep 8 - Sep 9
Total with taxes and fees
Travelodge by Wyndham Brattleboro VT
A lodge with a large building and a smaller annex, surrounded by dense forest and a clear road.

11. The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain
2.5 star property
Londonderry
8.2 out of 10, Very Good, (705 reviews)
"Very nice staff easy access to everything good for dogs clean pool"
United States
Terry
$86 nightly
The price is $95
Sep 14 - Sep 15
Total with taxes and fees
The Upper Pass Lodge at Magic Mountain
A spa named Castle Hill Spa with a well-maintained lawn and a pathway leading to the entrance.

12. Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
3.5 star property
Cavendish
8.8 out of 10, Excellent, (1,000 reviews)
"Nice location, clean hotel, pleasant staff"
United States
David
$116 nightly
The price is $126
Sep 8 - Sep 9
Total with taxes and fees
Pointe at Castle Hill Resort
A two-story white house with a porch, a front yard, and a mailbox.

13. Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (278 reviews)
"Beautiful views of the river excellent breakfast"
United States
Michael
$164 nightly
The price is $179
Sep 9 - Sep 10
Total with taxes and fees
Harvest Barn Inn
A large, two-story house with a stone foundation and white siding, surrounded by a well-maintained lawn and trees.

14. The Hartness House

The Hartness House
3.0 star property
Springfield
8.2 out of 10, Very Good, (351 reviews)
"Fantastic historic house in downtown Springfield, VT. A wonderful place to spend an evening or the weekend. Close to state parks, great restaurants, and kayaking. Wonderful place for a getaway."
United States
Dan
$142 nightly
The price is $156
Sep 7 - Sep 8
Total with taxes and fees
The Hartness House
A motel with a sign reading "Claremont Motor Lodge."

15. Claremont Motor Lodge

Claremont Motor Lodge
2.5 star property
Claremont
8.8 out of 10, Excellent, (578 reviews)
"- well equipped room: microwave, tv, coffee machine, fridge, AC, towels - very clean and neat - comfortable bed, sofa, and chairs - quiet - pleasant and helpful staff"
United States
EDWARD S
$103 nightly
The price is $112
Sep 9 - Sep 10
Total with taxes and fees
Claremont Motor Lodge
A hotel with multiple buildings, a covered outdoor area, and a snowy landscape.

16. Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property
3.0 star property
Jackson Gore Base Area
8.6 out of 10, Excellent, (890 reviews)
"The best place"
United States
Zulma
$192 nightly
The price is $211
Sep 30 - Oct 1
Total with taxes and fees
Jackson Gore Village, A Vail Resorts Property
A deck with white railings overlooking a forested area and a mountain in the distance.

17. Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (476 reviews)
"Pleasant stay - excellent breakfast!"
Canada
William
$85 nightly
The price is $93
Sep 8 - Sep 9
Total with taxes and fees
Bromley View Inn
A red house with a covered porch and a chimney.

18. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (171 reviews)
"We had a very lovely stay. The kitchen was well-equipped and the whole home was very cozy. There was wood for the wood stove and lots of games and puzzles to do. Check-in and check-out was simple. Just what we were looking for! "
United States
Eleanor D.
$330 nightly
The price is $370
Sep 7 - Sep 8
Total with taxes and fees
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
A two-story building with a bar and restaurant on the ground floor, a vintage car parked in front, and a sign indicating "Main Mountain".

19. Main and Mountain Bar & Motel

Main and Mountain Bar & Motel
2.0 star property
Ludlow
9.6 out of 10, Exceptional, (228 reviews)
"We really liked our stay. It was clean, quiet and safe. Comfy bed and very nice and clean bathroom. Very homey feel. Everyone was very helpful and friendly. Would certainly stay there again."
United States
Paull
$179 nightly
The price is $196
Sep 14 - Sep 15
Total with taxes and fees
Main and Mountain Bar & Motel
A two-story house with a red exterior and white trim. There are three large windows on the front and a chimney on the right side.

20. COHO Inn & Motor Lodge

COHO Inn & Motor Lodge
2.0 star property
Weston
9.4 out of 10, Exceptional, (77 reviews)
"Clean comfy rooms, amazing breakfast, friendly attentive staff, easy drive to Magic Mountain."
United States
Christopher
$198 nightly
The price is $216
Sep 6 - Sep 7
Total with taxes and fees
COHO Inn & Motor Lodge
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

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"All around great stay. Thank you."
Christina 3-night trip
Posted 11 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel

Find out more about Chester

Chester Villas information

Number of reviews
4,300
Accommodation
27 Villas
Lowest Price
$92
Highest Price
$1,007

Frequently asked questions

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What is there to do near my villa in Chester?
If you want to make the most of your time in Chester, don't miss DaVallia Art & Accents. It's a favorite with locals and travelers alike.

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