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Check prices for these dates

Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov
In one month
21 Nov - 23 Nov
In two months
19 Dec - 21 Dec

Motels in Chester

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
2.5 star property
8.2 out of 10, Very Good, (678)
"The staff was helpful "
United States
Mohammed
The price is AED 288
AED 317 total
includes taxes & fees
3 Nov - 4 Nov
The Upper Pass Lodge at Magic Mountain
Deluxe Suite | 2 bedrooms, individually decorated, desk, blackout drapes
Sleep Woodstock Motel
Sleep Woodstock Motel
2.0 star property
9.6 out of 10, Exceptional, (538)
"Great motel with complete amenities.. beautiful surrounding especially in this fall"
United States
Giana
The price is AED 380
AED 479 total
includes taxes & fees
28 Oct - 29 Oct
Sleep Woodstock Motel
Exterior
The Putney Inn
The Putney Inn
2.5 star property
8.4 out of 10, Very Good, (1002)
"Reasonable price for an overnight stay. Ample parking, very quiet and easy access to I 91."
United States
MICHAEL
The Putney Inn
Room, 2 Queen Beds, Non Smoking, Refrigerator & Microwave | 1 bedroom, premium bedding, in-room safe, individually decorated
Claremont Motor Lodge
Claremont Motor Lodge
2.5 star property
8.8 out of 10, Excellent, (428)
"It was clean safe and staff was is friendly and helpful "
United States
Anthony
The price is AED 406
AED 440 total
includes taxes & fees
2 Nov - 3 Nov
Claremont Motor Lodge
Front of property
Brittany Motel
Brittany Motel
2.0 star property
9.4 out of 10, Exceptional, (321)
"I only stayed one night at The Brittany but I enjoyed it. It's a no frills kind of stay but the room I had was up to date, clean, and the bed was really comfortable. Reasonable price too. Exactly what I was looking for. "
United States
Bruce
The price is AED 422
AED 525 total
includes taxes & fees
26 Oct - 27 Oct
Brittany Motel
Family Room | Living area | Smart TV
Chalet 239
Chalet 239
2.0 star property
9.4 out of 10, Exceptional, (84)
"Great place for a quick trip to VT!"
United States
Rory
The price is AED 410
AED 451 total
includes taxes & fees
2 Nov - 3 Nov
Chalet 239
Interior
The Olympia Lodge
The Olympia Lodge
2.5 star property
9.4 out of 10, Exceptional, (554)
"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 621
AED 683 total
includes taxes & fees
25 Nov - 26 Nov
The Olympia Lodge
Mountain view
Aerie Inn of Vermont
Aerie Inn of Vermont
2.0 star property
9.4 out of 10, Exceptional, (178)
"This was an absolutely beautiful place to stay to look at the foliage of the mountains. The coffee was fantastic. The host was super friendly and I would highly recommend it."
United States
Nancy
The price is AED 465
AED 506 total
includes taxes & fees
27 Oct - 28 Oct
Aerie Inn of Vermont
Restaurant
COHO Inn & Motor Lodge
COHO Inn & Motor Lodge
2.0 star property
9.4 out of 10, Exceptional, (41)
"We loved our stay at COHO. Breakfast was wonderful and the owners are so sweet and knowledgeable about the history of the place and the area! Great location near Weston and ludlow"
United States
Roy
COHO Inn & Motor Lodge
Lobby
Rodeway Inn Bellows Falls
Rodeway Inn Bellows Falls
2.0 star property
6.2 out of 10, (286)
"Clean room. Very basic. Easy access to the interstate."
United States
Bruce
The price is AED 309
AED 337 total
includes taxes & fees
23 Nov - 24 Nov
Rodeway Inn Bellows Falls
Fireplace
Mountaineer Inn
Mountaineer Inn
2.0 star property
8.6 out of 10, Excellent, (536)
"Easy check in and out. Beautiful location"
United States
Bill
Mountaineer Inn
Lobby
Four Winds Country Motel
Four Winds Country Motel
2.0 star property
8.4 out of 10, Very Good, (519)
"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
2 Nov - 3 Nov
Four Winds Country Motel
Standard Room, 1 Queen Bed | Desk, blackout drapes, iron/ironing board, free WiFi
Royal Inn Claremont
Royal Inn Claremont
2.0 star property
6.6 out of 10, (316)
"Affordable"
United States
Cheryl
The price is AED 414
AED 450 total
includes taxes & fees
26 Oct - 27 Oct
Royal Inn Claremont
Reception
Travelodge by Wyndham Brattleboro VT
Travelodge by Wyndham Brattleboro VT
2.5 star property
6.0 out of 10, (726)
"Reasonable rate for the the accomadations."
United States
David
The price is AED 294
AED 324 total
includes taxes & fees
27 Oct - 28 Oct
Travelodge by Wyndham Brattleboro VT
Exterior
Colonial Motel And Spa
Colonial Motel And Spa
3.0 star property
6.8 out of 10, (1002)
"Nice place to stay for the night."
United States
Robin
The price is AED 514
AED 566 total
includes taxes & fees
26 Oct - 27 Oct
Colonial Motel And Spa
Fountain
Weathervane Motel
Weathervane Motel
2.0 star property
6.8 out of 10, (718)
"Good location, good value "
United States
Jacqueline
The price is AED 393
AED 433 total
includes taxes & fees
26 Oct - 27 Oct
Weathervane Motel
Front of property - evening/night
Main and Mountain Bar & Motel
Main and Mountain Bar & Motel
2.0 star property
9.6 out of 10, Exceptional, (210)
"Amazing place to stay "
United States
KYLE
Main and Mountain Bar & Motel
View from room
Econo Lodge Brattleboro
Econo Lodge Brattleboro
2.0 star property
5.4 out of 10, (583)
"Most disgusting place I've ever seen to"
United States
Edward
The price is AED 200
AED 220 total
includes taxes & fees
23 Nov - 24 Nov
Econo Lodge 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.
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Top Chester Hotel Reviews

Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Highly recommend stay here"
Margie 1-night trip
Posted 1 day ago
Woodstock Inn & Resort

Frequently asked questions

What can I expect from a motel trip to Chester?
If you can't find a motel in Chester, consider some of the motels we suggest around the area or let Expedia help you find something similar from over 67 lodging options. Simply filter using our search tools by price per night or cost-effective amenities such as free breakfast and free airport transportation.
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. Econo Lodge Brattleboro: Enjoy access to the seasonal outdoor pool, and freebies including breakfast, WiFi, and parking. Located 29.4 mi (47.3 km) from the heart of Chester. Claremont Motor Lodge: Central Chester is 14.7 mi (23.7 km) away. Free WiFi and free parking are available during your stay, along with room amenities like air conditioning. Colonial Motel And Spa: 26.6 mi (42.8 km) from the heart of Chester. Enjoy access to the 2 indoor pools, and freebies including WiFi and parking.
What things can I to do in Chester?
As you explore this relaxing, quaint 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 Grafton Historical Society, Vermont Country Store, and Plummer's Sugar House.
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.