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

Search Motels in Chester from CA $127

  • 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
Sep 11 - Sep 13
In two weeks
Sep 18 - Sep 20
In one month
Oct 2 - Oct 4
In two months
Oct 30 - Nov 1

Our top choices for Chester motels

Restaurant

1. 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, (704 reviews)
"Very nice staff easy access to everything good for dogs clean pool"
United States
Terry
The price is CA $119
CA $132 total
includes taxes & fees
Sep 7 - Sep 8
The Upper Pass Lodge at Magic Mountain
Room, 2 Queen Beds, Non Smoking, Refrigerator & Microwave

2. Claremont Motor Lodge

Claremont Motor Lodge
2.5 star property
Claremont
8.8 out of 10, Excellent, (577 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
The price is CA $166
CA $180 total
includes taxes & fees
Sep 6 - Sep 7
Claremont Motor Lodge
Front of property - evening/night

3. 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
The price is CA $240
CA $264 total
includes taxes & fees
Sep 9 - Sep 10
Main and Mountain Bar & Motel
Standard Room, 2 Double Beds

4. Royal Inn Claremont

Royal Inn Claremont
2.0 star property
Claremont
6.8 out of 10, (352 reviews)
"I like it was clean bathroom was new."
United States
Eva
The price is CA $156
CA $169 total
includes taxes & fees
Sep 6 - Sep 7
Royal Inn Claremont
Luxury Room, 2 Double Beds (Room 19)

5. Otherland Hotel

Otherland Hotel
2.5 star property
Newfane
9.6 out of 10, Exceptional, (217 reviews)
"Clean, modern, and peaceful."
Canada
Omar
The price is CA $204
CA $266 total
includes taxes & fees
Sep 7 - Sep 8
Otherland Hotel
Deluxe Suite | Private kitchen

6. Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (608 reviews)
"Centrally located to waterfalls we went to Had everything we needed"
United States
John
The price is CA $121
CA $133 total
includes taxes & fees
Sep 7 - Sep 8
Sleep Woodstock Motel
Mountain view

7. Aerie Inn of Vermont

Aerie Inn of Vermont
2.0 star property
East Dorset
9.4 out of 10, Exceptional, (188 reviews)
"Very comfortable room and nice staff. Will stay there again. "
United States
Laura
The price is CA $183
CA $199 total
includes taxes & fees
Sep 6 - Sep 7
Aerie Inn of Vermont
Exterior

8. The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1,001 reviews)
"Clean room, staff, breakfast, and parking were great!"
United States
JANE
The price is CA $151
CA $166 total
includes taxes & fees
Sep 6 - Sep 7
The Putney Inn
Signature Suite, Kitchen, Mountain View | Living area

9. Brittany Motel

Brittany Motel
2.0 star property
Manchester Center
9.4 out of 10, Exceptional, (415 reviews)
"Quiet and comfortable."
United States
Claire
The price is CA $119
CA $131 total
includes taxes & fees
Sep 15 - Sep 16
Brittany Motel
Interior

10. The Olympia Lodge

The Olympia Lodge
2.5 star property
Manchester Center
9.4 out of 10, Exceptional, (603 reviews)
"amazing breakfast!"
United States
Matheus
The price is CA $276
CA $303 total
includes taxes & fees
Sep 7 - Sep 8
The Olympia Lodge
Free continental breakfast on weekends

11. Four Winds Country Motel

Four Winds Country Motel
2.0 star property
Manchester Center
8.4 out of 10, Very good, (559 reviews)
"The room was really nice. It has just been remodeled."
United States
Anthony
The price is CA $179
CA $196 total
includes taxes & fees
Sep 6 - Sep 7
Four Winds Country Motel
Lobby

12. Colonial Motel

Colonial Motel
3.0 star property
Brattleboro
6.8 out of 10, (48 reviews)
"Clean room ez checkin, coffee at breakfast good!"
United States
James
The price is CA $115
CA $127 total
includes taxes & fees
Sep 6 - Sep 7
Colonial Motel
Lobby sitting area

13. Chalet 239

Chalet 239
2.0 star property
West Dover
9.4 out of 10, Exceptional, (143 reviews)
"Perfect boutique stay"
United States
Michelle
The price is CA $151
CA $167 total
includes taxes & fees
Sep 16 - Sep 17
Chalet 239
Fountain

14. Weathervane Motel

Weathervane Motel
2.0 star property
Manchester Center
6.8 out of 10, (800 reviews)
"Good location."
United States
cody
The price is CA $148
CA $163 total
includes taxes & fees
Sep 6 - Sep 7
Weathervane Motel
Reception

15. 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
The price is CA $116
CA $127 total
includes taxes & fees
Sep 8 - Sep 9
Travelodge by Wyndham Brattleboro VT
Seasonal outdoor pool

16. Econo Lodge Brattleboro South

Econo Lodge Brattleboro South
2.0 star property
Brattleboro
5.2 out of 10, (680 reviews)
"I was given a key to an occupied room first, then moved to a room that a smoker used, and lastly a musty room that I used. It did have A/C and windows to the parking lot. There is a swimming pool in the center available for tenants."
United States
David
The price is CA $138
CA $151 total
includes taxes & fees
Oct 4 - Oct 5
Econo Lodge Brattleboro South
Front of property

17. COHO Inn & Motor Lodge

COHO Inn & Motor Lodge
2.0 star property
Weston
9.4 out of 10, Exceptional, (76 reviews)
"Clean comfy rooms, amazing breakfast, friendly attentive staff, easy drive to Magic Mountain."
United States
Christopher
The price is CA $247
CA $269 total
includes taxes & fees
Sep 7 - Sep 8
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.
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

The Manchester View

The Manchester View

10/10 Excellent
"The room was beautiful and clean with a great view. The breakfast was delicious and plentiful. I highly recommend the place."
Jannette 1-night trip
Posted 20 hours ago
The Manchester View

Find out more about Chester

Chester Motels information

Number of reviews
5,425
Accommodation
24 Motels
Lowest Price
CA $127
Highest Price
CA $303

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 62 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. Claremont Motor Lodge: Enjoy access to the free WiFi and free parking, as well as room amenities like air conditioning. Located 14.7 mi (23.7 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. Brittany Motel: 26.7 mi (42.9 km) from the heart of Chester. Enjoy access to the snack bar/deli, 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, Connecticut River State Park, and Buttermilk Falls. 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