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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for Chester motels

Deluxe Suite | Individually decorated, desk, blackout drapes, iron/ironing board
Sleep Woodstock Motel

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
The price is AED 284
AED 603 total
includes taxes & fees
14 Dec - 15 Dec
Sleep Woodstock Motel
Room, 2 Queen Beds, Non Smoking, Refrigerator & Microwave | Premium bedding, in-room safe, individually decorated
Claremont Motor Lodge

Claremont Motor Lodge

Claremont Motor Lodge
2.5 star property
Claremont
8.8 out of 10, Excellent, (446)
"Great place"
United States
brier
The price is AED 388
AED 421 total
includes taxes & fees
14 Dec - 15 Dec
Claremont Motor Lodge
Family Room | Living area | Smart TV
Chalet 239

Chalet 239

Chalet 239
2.0 star property
West Dover
9.4 out of 10, Exceptional, (89)
"Great place for a quick trip to VT!"
United States
Rory
The price is AED 476
AED 524 total
includes taxes & fees
11 Dec - 12 Dec
Chalet 239
Front of property
Brittany Motel

Brittany Motel

Brittany Motel
2.0 star property
Manchester Center
9.4 out of 10, Exceptional, (326)
"Well, being that it was self check in I did not interact with the staff. I loved the room an thought the little xmas tree was an awesome touch. If I'm ever staying in the area again I will definitely stay there."
United States
Joseph
The price is AED 290
AED 481 total
includes taxes & fees
15 Dec - 16 Dec
Brittany Motel
Exterior
The Putney Inn

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very Good, (1000)
"Nice motel. "
United States
Richard
The Putney Inn
Exclusive Suite, 3 Bedrooms, Kitchenette, Mountain View - Pet Friendly | 1 bedroom, desk, iron/ironing board, free WiFi
The Upper Pass Lodge at Magic Mountain

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, (686)
"Wery good diner"
United States
Yelena
The price is AED 412
AED 457 total
includes taxes & fees
4 Jan - 5 January 2026
The Upper Pass Lodge at Magic Mountain
Restaurant
COHO Inn & Motor Lodge

COHO Inn & Motor Lodge

COHO Inn & Motor Lodge
2.0 star property
Weston
9.2 out of 10, Wonderful, (44)
"The owner was delightful and very accommodating. "
United States
Karen
The price is AED 484
AED 527 total
includes taxes & fees
16 Dec - 17 Dec
COHO Inn & Motor Lodge
Lobby
Four Winds Country Motel

Four Winds Country Motel

Four Winds Country Motel
2.0 star property
Manchester Center
8.4 out of 10, Very Good, (520)
"The check in was very quick and staff was friendly. The room is clean, comfortable, and quiet. "
United States
Alicia
The price is AED 400
AED 440 total
includes taxes & fees
11 Dec - 12 Dec
Four Winds Country Motel
Interior
The Olympia Lodge

The Olympia Lodge

The Olympia Lodge
2.5 star property
Manchester Center
9.4 out of 10, Exceptional, (563)
"Great little inn. Has a wonderful home feeling. The owners are super friendly and made the stay a great experience."
United States
Holly
The price is AED 643
AED 707 total
includes taxes & fees
15 Dec - 16 Dec
The Olympia Lodge
Exterior
Colonial Motel And Spa

Colonial Motel And Spa

Colonial Motel And Spa
3.0 star property
Brattleboro
6.8 out of 10, (1001)
"Nice place to stay for the night."
United States
Robin
The price is AED 441
AED 485 total
includes taxes & fees
15 Dec - 16 Dec
Colonial Motel And Spa
Reception
Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT
2.5 star property
Brattleboro
6.0 out of 10, (736)
"Reasonable rate for the the accomadations."
United States
David
The price is AED 261
AED 287 total
includes taxes & fees
15 Dec - 16 Dec
Travelodge by Wyndham Brattleboro VT
Standard Room, 1 Queen Bed | Desk, blackout drapes, iron/ironing board, free WiFi
Royal Inn Claremont

Royal Inn Claremont

Royal Inn Claremont
2.0 star property
Claremont
6.6 out of 10, (318)
"Affordable"
United States
Cheryl
The price is AED 392
AED 425 total
includes taxes & fees
24 Dec - 25 Dec
Royal Inn Claremont
Front of property - evening/night
Main and Mountain Bar & Motel

Main and Mountain Bar & Motel

Main and Mountain Bar & Motel
2.0 star property
Ludlow
9.6 out of 10, Exceptional, (211)
"The bar was wonderful! Clean and great guest services"
United States
Mariah
The price is AED 841
AED 925 total
includes taxes & fees
15 Dec - 16 Dec
Main and Mountain Bar & Motel
View from room
Econo Lodge Brattleboro

Econo Lodge Brattleboro

Econo Lodge Brattleboro
2.0 star property
Brattleboro
5.4 out of 10, (601)
"Room was dirty, tv was tiny..very poor value"
United States
Raymond
The price is AED 190
AED 209 total
includes taxes & fees
16 Dec - 17 Dec
Econo Lodge Brattleboro
Fountain
Weathervane Motel

Weathervane Motel

Weathervane Motel
2.0 star property
Manchester Center
6.8 out of 10, (728)
"Everything was great and we will stay there again 😁"
United States
Pasquale
The price is AED 393
AED 433 total
includes taxes & fees
11 Dec - 12 Dec
Weathervane Motel
Lobby
Rodeway Inn Bellows Falls

Rodeway Inn Bellows Falls

Rodeway Inn Bellows Falls
2.0 star property
Bellows Falls
6.2 out of 10, (288)
"Clean room. Very basic. Easy access to the interstate."
United States
Bruce
The price is AED 393
AED 429 total
includes taxes & fees
17 Dec - 18 Dec
Rodeway Inn Bellows Falls
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 Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

10/10 Excellent
"Nice staff, big room, comfortable bed, walking distance to downtown-overall great stay! "
Amanda 1-night trip
Posted 3 days ago
The Palmer House Resort, an Ascend Collection Hotel

Frequently asked questions

What can I expect from a motel trip to Chester?
Because you'll save on your room price, you can make the most of what Chester has to offer. In the area, favorite places to visit include Stratton Mountain Resort.
What are motels like?
At most motels, you'll often find free parking and an outdoor pool. When you stay at a motel, you'll usually access your room directly from the parking lot. The word "motel" was coined in 1925 by the owner of the Milestone Mo-Tel in San Luis Obispo, California.
What are the best motels in Chester?
These are some of Expedia customers' favorite motels in the larger area. Motel in the Meadow: If driving, you'll be within 26 minutes of Okemo Mountain Resort. Enjoy the in-room free WiFi, and freebies including breakfast and parking. Mountaineer Inn: A seasonal outdoor pool and free WiFi are available during your stay, along with room amenities like air conditioning. Central Chester is 25.5 mi (41.1 km) away. The Putney Inn: Enjoy access to the 24-hour front desk, and freebies including breakfast, WiFi, and parking. Located 21 mi (33.8 km) from the heart of Chester. Sleep Woodstock Motel: Central Chester is 23.2 mi (37.3 km) away. Free WiFi, free parking, and a picnic area are available during your stay. Chalet 239: 25.8 mi (41.6 km) from the heart of Chester. Enjoy access to the picnic area, and freebies including breakfast, WiFi, and parking.
What things can I to do in Chester?
As you explore this quaint, relaxing area, check out the ski slopes. Visitors like Chester for its shops, coffeehouses, and restaurants. Some outdoorsy places nearby include Lowell Lake State Park, Buttermilk Falls, and Lake Rescue. Attractions the whole family can enjoy include DaVallia Art & Accents and Bonnie's Bundles Dolls. While you're checking out the area, consider visiting Stratton Mountain Resort, Grafton Historical Society, and Vermont Country Store.
What's the weather like in Chester?
Weather can make or break a roadtrip, so here's some data about year-round temperatures in Chester to help you plan yours: The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chester are January, March, November, and February, with each month seeing an average of 14 inches of snowfall.
What are my options for getting around Chester when staying in a motel?
We've gathered some information about local transportation options in Chester to help you navigate your stay: Fly into Springfield, VT (VSF-Hartness State), which is located 6.6 mi (10.7 km) from the heart of the city. Otherwise, you can search for flights to Rutland, VT (RUT-Rutland Southern Vermont Regional), which is 25.4 mi (40.8 km) away. If you'd like to venture out around the area, you may want a rental car for your journey.