Lodging Image

Search Motels in Chester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Jul 24 - Jul 26
In two weeks
Jul 31 - Aug 2
In one month
Aug 14 - Aug 16
In two months
Sep 11 - Sep 13

Our top choices for Chester motels

Restaurant

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, (701 reviews)
"Charming rustic inn. Staff were delightful and food was great. "
United States
Bradley
The price is CA $151
CA $167 total
includes taxes & fees
Aug 17 - Aug 18
The Upper Pass Lodge at Magic Mountain
Room, 2 Queen Beds, Non Smoking, Refrigerator & Microwave

Claremont Motor Lodge

Claremont Motor Lodge
2.5 star property
Claremont
8.8 out of 10, Excellent, (540 reviews)
"Nice place to stay"
United States
Shane
The price is CA $142
CA $154 total
includes taxes & fees
Jul 21 - Jul 22
Claremont Motor Lodge
Standard Room, 2 Double Beds

Royal Inn Claremont

Royal Inn Claremont
2.0 star property
Claremont
6.8 out of 10, (345 reviews)
"I like it was clean bathroom was new."
United States
Eva
The price is CA $139
CA $151 total
includes taxes & fees
Jul 20 - Jul 21
Royal Inn Claremont
Front of property - evening/night

Main and Mountain Bar & Motel

Main and Mountain Bar & Motel
2.0 star property
Ludlow
9.6 out of 10, Exceptional, (224 reviews)
"Comfy beds , great shower and awesome coffee room !"
United States
Kristina
The price is CA $205
CA $225 total
includes taxes & fees
Jul 27 - Jul 28
Main and Mountain Bar & Motel
Signature Suite, Kitchen, Mountain View | Living area

Brittany Motel

Brittany Motel
2.0 star property
Manchester Center
9.4 out of 10, Exceptional, (387 reviews)
"The property was comfortable. Felt safe and the room was cozy and nicely decorated"
United States
Samantha
The price is CA $121
CA $133 total
includes taxes & fees
Jul 20 - Jul 21
Brittany Motel
Deluxe Suite | Private kitchen

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (593 reviews)
"Love that they catered to my dog. Will be back!"
United States
Mark
The price is CA $109
CA $119 total
includes taxes & fees
Jul 22 - Jul 23
Sleep Woodstock Motel
Exterior

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1,003 reviews)
"Perfect for an overnight!"
United States
Lori
The price is CA $173
CA $190 total
includes taxes & fees
Aug 7 - Aug 8
The Putney Inn
Mountain view

Aerie Inn of Vermont

Aerie Inn of Vermont
2.0 star property
East Dorset
9.4 out of 10, Exceptional, (183 reviews)
"Very comfortable room and nice staff. Will stay there again. "
United States
Laura
The price is CA $185
CA $202 total
includes taxes & fees
Aug 9 - Aug 10
Aerie Inn of Vermont
Interior

The Olympia Lodge

The Olympia Lodge
2.5 star property
Manchester Center
9.4 out of 10, Exceptional, (597 reviews)
"The owners are incredibly warm and welcoming. We would absolutely stay again."
United States
Susan
The price is CA $265
CA $292 total
includes taxes & fees
Jul 20 - Jul 21
The Olympia Lodge
Lobby sitting area

Chalet 239

Chalet 239
2.0 star property
West Dover
9.4 out of 10, Exceptional, (133 reviews)
"Staff very helpful. Everything was very clean"
United States
Patrick
The price is CA $164
CA $180 total
includes taxes & fees
Jul 26 - Jul 27
Chalet 239
Reception

Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT
2.5 star property
Brattleboro
6.0 out of 10, (787 reviews)
"Good value!"
United States
Brian
The price is CA $110
CA $121 total
includes taxes & fees
Aug 5 - Aug 6
Travelodge by Wyndham Brattleboro VT
Fountain

Weathervane Motel

Weathervane Motel
2.0 star property
Manchester Center
6.8 out of 10, (784 reviews)
"EXTREMELY helpful manager! Great shower, great bathroom."
United States
Scott
The price is CA $150
CA $165 total
includes taxes & fees
Jul 20 - Jul 21
Weathervane Motel
Free continental breakfast on weekends

Four Winds Country Motel

Four Winds Country Motel
2.0 star property
Manchester Center
8.4 out of 10, Very good, (552 reviews)
"We had a very enjoyable stay, and the breakfast had many items which appealed to us. We will stay at this hotel again."
United States
CHARLES
The price is CA $237
CA $261 total
includes taxes & fees
Aug 16 - Aug 17
Four Winds Country Motel
Lobby

Colonial Motel

Colonial Motel
3.0 star property
Brattleboro
5.8 out of 10, (22 reviews)
"Clean room ez checkin, coffee at breakfast good!"
United States
James
The price is CA $107
CA $118 total
includes taxes & fees
Aug 2 - Aug 3
Colonial Motel
Seasonal outdoor pool

Econo Lodge Brattleboro South

Econo Lodge Brattleboro South
2.0 star property
Brattleboro
5.2 out of 10, (660 reviews)
"Quiet and clean place to stay the night"
United States
Aigul
The price is CA $118
CA $130 total
includes taxes & fees
Aug 17 - Aug 18
Econo Lodge Brattleboro South
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"Thoughtful and attentive staff"
Charles 1-night trip
Posted 11 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel

Find out more about Chester

Chester Motels information

Number of reviews
Accommodation
 Motels
Lowest Price
Highest Price

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 64 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: Stay within a 30-minute drive of Green Mountain National Forest and Okemo Mountain Resort. Enjoy the in-room free WiFi, and freebies including breakfast and parking. Colonial Motel: A 24-hour front desk along with freebies like breakfast, WiFi, and parking are available during your stay. Central Chester is 26.6 mi (42.8 km) away. Brittany Motel: Enjoy access to the snack bar/deli, and freebies including WiFi and parking. Located 26.7 mi (42.9 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. Sleep Woodstock Motel: 23.2 mi (37.3 km) from the heart of Chester. Enjoy the in-room kitchenette, and freebies including 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 Vermont Country Store, Magic Mountain Ski Resort, and Viking Nordic Center.
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.

Explore a world of travel with Expedia