Villas in Chester

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Recommended hotels in Chester

Fullerton Inn

Fullerton Inn
2.5 star property
Chester Depot
8.2 out of 10, Very Good, (402)
"Lovely stay"
United States
Christine
$129 nightly
The price is $141
Dec 16 - Dec 17
Total with taxes and fees
Fullerton Inn

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (107)
"Good breakfast and dinner options. Great location for hiking."
United States
Paul
$211 nightly
The price is $231
Dec 30 - Dec 31
Total with taxes and fees
Stone Hearth Inn and Eatery

Quaint Queen room at the Chester Inn

Quaint Queen room at the Chester Inn
2.0 star property
Chester Depot
10.0 out of 10, Exceptional, (1)
"This was a wonderful experience for us. The Inn and room were spotless. Very comfortable bed. We will return. The only issue was the tub/shore. Too much of a challenge for older folks. "
United States
Thomas
$182 nightly
The price is $204
Dec 14 - Dec 15
Total with taxes and fees
Quaint Queen room at the Chester Inn

Room in Historic Inn! 20 Minutes to Okemo!

Room in Historic Inn! 20 Minutes to Okemo!
Chester Depot
9.2 out of 10, Wonderful, (18)
"The Chester Inn was beautiful and located in downtown Chester. "
United States
Peter C.
$171 nightly
The price is $192
Dec 14 - Dec 15
Total with taxes and fees
Room in Historic Inn! 20 Minutes to Okemo!

Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!

Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Chester Depot
9.0 out of 10, Wonderful, (2)
"Property seemed well-maintained and cared for. We were only there a short time, but it was well put together. The check-in process was a little hectic, check in time was 3pm, but our room wasn't ready. The caretaker was very friendly. We only had to wait about 20 minutes. We weren't aware this property was a VRBO, and not a regular Inn. "
United States
Jacque
$198 nightly
The price is $222
Dec 13 - Dec 14
Total with taxes and fees
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!

Whimsical Room & Private Bathroom in Historic Inn

Whimsical Room & Private Bathroom in Historic Inn
Chester Depot
8.8 out of 10, Excellent, (9)
"After a long month of work I needed a weekend in VT to calm the nerves. This was a beautiful spot to be in, glad I was here!"
United States
Paul S.
$181 nightly
The price is $203
Dec 14 - Dec 15
Total with taxes and fees
Whimsical Room & Private Bathroom in Historic Inn

Historic 150-year-old farmhouse, Jacuzzi included

Historic 150-year-old farmhouse, Jacuzzi included
Chester Depot
9.8 out of 10, Exceptional, (10)
"This was a lovely inviting piece of history to stay in! The amenities were wonderful, the host very engaged with being sure we had what we needed. It is (for those who may not know Vermont) SUPER close to all sorts of hiking, tours, cute stores and great food! Our family will absolutely stay here again!"
United States
Amy S.
$419 nightly
The price is $469
Dec 14 - Dec 15
Total with taxes and fees
Historic 150-year-old farmhouse, Jacuzzi included

Chester Farmhouse Ski Retreat near Slopes

Chester Farmhouse Ski Retreat near Slopes
Chester Depot
9.6 out of 10, Exceptional, (17)
"This was my second time staying at this property. Everything was great just like last year. I highly recommend it if you are staying in Chester, VT. "
United States
Lori N.
$374 nightly
The price is $419
Jan 7 - Jan 8, 2026
Total with taxes and fees
Chester Farmhouse Ski Retreat near Slopes

Cozy Vermont Cabin · Mountain Views · Near Okemo

Cozy Vermont Cabin · Mountain Views · Near Okemo
Chester
10.0 out of 10, Exceptional, (3)
"We really enjoyed our stay at this home. It had everything we needed and was very comfortable. The countryside around this part of Vermont is beautiful. We found lots of great museums and restaurants. "
United States
Donald M.
$902 nightly
The price is $1,010
Dec 13 - Dec 14
Total with taxes and fees
Cozy Vermont Cabin · Mountain Views · Near Okemo

King & Queen Suite in Historic Inn Circa 1780

King & Queen Suite in Historic Inn Circa 1780
Chester Depot
9.8 out of 10, Exceptional, (16)
"Central for our needs. easy check in process. Lovely large room with comfy beds. "
United States
HIlary H.
$340 nightly
The price is $381
Jan 3 - Jan 4, 2026
Total with taxes and fees
King & Queen Suite in Historic Inn Circa 1780

Honeymoon Suite with Jacuzzi Tub in Historic Inn

Honeymoon Suite with Jacuzzi Tub in Historic Inn
Chester Depot
8.6 out of 10, Excellent, (7)
"Charming place, hope to go back soon."
United States
Sharon S.
$308 nightly
The price is $345
Dec 14 - Dec 15
Total with taxes and fees
Honeymoon Suite with Jacuzzi Tub in Historic Inn

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow
2.0 star property
West Dover
10.0 out of 10, Exceptional, (2)
"Tout y était!"
Canada
Martin
$149 nightly
The price is $164
Dec 14 - Dec 15
Total with taxes and fees
Hideaway Inn Mt. Snow

Best Western Springfield Hotel

Best Western Springfield Hotel
2.5 star property
Springfield
8.8 out of 10, Excellent, (804)
"so clean and friendly it was a perfect stay!"
United States
Colette
$143 nightly
The price is $157
Dec 18 - Dec 19
Total with taxes and fees
Best Western Springfield Hotel

The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1001)
"Quiet, easy to get to right off the highway with lots of quick eats within walking distance. Staff was friendly and helpful with any requests."
United States
Zachery
$70 nightly
The price is $77
Jan 10 - Jan 11, 2026
Total with taxes and fees
The Covered Bridge Inn

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.4 out of 10, Very Good, (960)
"Staff were very friendly. The pool was the perfect temperature. Would definitely stay again. "
United States
Tiffany
$115 nightly
The price is $125
Dec 14 - Dec 15
Total with taxes and fees
Keene Elm City Hotel, an Ascend Collection Hotel

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (548)
"The staff at this motel are 5 star! Lisa went above and beyond to make my stay easy since I was there for a medical procedure. "
United States
Crystal
$158 nightly
The price is $174
Dec 14 - Dec 15
Total with taxes and fees
Sleep Woodstock Motel

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (353)
"Clean comfy nice staff "
United States
Katherine
$147 nightly
The price is $160
Dec 23 - Dec 24
Total with taxes and fees
Hampton Inn & Suites Keene

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (739)
"Staff was friendly and pool was nice"
United States
Joshua
$107 nightly
The price is $118
Dec 14 - Dec 15
Total with taxes and fees
Comfort Inn & Suites Brattleboro I-91

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very Good, (1001)
"Great staff, clean room, nice breakfast"
United States
DORTHY
$139 nightly
The price is $151
Dec 14 - Dec 15
Total with taxes and fees
Best Western Plus Keene Hotel

Claremont Motor Lodge

Claremont Motor Lodge
2.5 star property
Claremont
8.8 out of 10, Excellent, (446)
"Great place"
United States
brier
$101 nightly
The price is $110
Dec 16 - Dec 17
Total with taxes and fees
Claremont 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

Find out more about Chester

Chester Villas information

Number of reviews
6,426
Accommodation
14 Villas
Lowest Price
$77
Highest Price
$1,010

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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