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Check prices for these dates

Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct
In one month
6 Nov - 8 Nov
In two months
4 Dec - 6 Dec

Our top choices for Chester motels

A restaurant with wooden tables and chairs, a central table with a sign reading "The Red Slate Restaurant", and large windows with views of the outside.

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, (710 reviews)
"Very nice staff easy access to everything good for dogs clean pool"
United States
Terry
The price is €99
includes taxes & fees
12 Oct - 13 Oct
The Upper Pass Lodge at Magic Mountain
A two-story building with a bar and restaurant on the ground floor, a vintage car parked in front, and a sign indicating "Main Mountain".

2. Main and Mountain Bar & Motel

Main and Mountain Bar & Motel
2.0 star property
Ludlow
9.6 out of 10, Exceptional, (230 reviews)
"Very cool hotel and bar"
United States
Patricia
The price is €198
includes taxes & fees
19 Oct - 20 Oct
Main and Mountain Bar & Motel
A hotel room with two beds, a wooden headboard, bedside lamps, and a window with curtains.

3. Claremont Motor Lodge

Claremont Motor Lodge
2.5 star property
Claremont
8.8 out of 10, Excellent, (595 reviews)
"Older hotel but thats has some upkeep. Accomodating host."
Australia
Alastair
The price is €116
includes taxes & fees
18 Oct - 19 Oct
Claremont Motor Lodge
A two-story house with a red exterior and white trim. There are three large windows on the front and a chimney on the right side.

4. COHO Inn & Motor Lodge

COHO Inn & Motor Lodge
2.0 star property
Weston
9.4 out of 10, Exceptional, (77 reviews)
"This may have been one of the best places that I’ve ever seen"
United States
Raedene
The price is €200
includes taxes & fees
15 Oct - 16 Oct
COHO Inn & Motor Lodge
A sign for The Putney Inn, a restaurant and motel, with a friendly welcome message and floral decorations.

5. The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1,008 reviews)
"The property was clean and well maintained. Enjoyed our stay."
United States
Anita
The price is €83
includes taxes & fees
25 Oct - 26 Oct
The Putney Inn
A modern bedroom with two beds, wooden headboards, a bench, a small table, and a large window with a view of greenery.

6. Otherland Hotel

Otherland Hotel
2.5 star property
Newfane
9.6 out of 10, Exceptional, (224 reviews)
"Clean, modern, and peaceful."
Canada
Omar
The price is €189
includes taxes & fees
1 Nov - 2 Nov
Otherland Hotel
A cozy living room with two sofas, a coffee table, and a lamp. There is a wooden ceiling with exposed beams and a ceiling fan.

7. The Olympia Lodge

The Olympia Lodge
2.5 star property
Manchester Center
9.4 out of 10, Exceptional, (611 reviews)
"amazing breakfast!"
United States
Matheus
The price is €190
includes taxes & fees
30 Oct - 31 Oct
The Olympia Lodge
A spacious kitchen with wooden cabinets, a large island, and a dining area with floral tablecloths.

8. Four Winds Country Motel

Four Winds Country Motel
2.0 star property
Manchester Center
8.4 out of 10, Very good, (569 reviews)
"Nice place, clean and good amenities, but did not have hair dryers. Would go again!"
United States
Shelley
The price is €114
includes taxes & fees
1 Nov - 2 Nov
Four Winds Country Motel
A modern kitchen with a central island, stainless steel appliances, and a dining area with chairs.

9. Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (632 reviews)
"Such a cute motel! Very clean and on the outskirts of town making a quiet place to stay!"
United States
michelle
The price is €101
includes taxes & fees
9 Nov - 10 Nov
Sleep Woodstock Motel
A spacious living area with a high ceiling, a wooden staircase, and a built-in kitchen visible through an open door.

10. Brittany Motel

Brittany Motel
2.0 star property
Manchester Center
9.2 out of 10, Wonderful, (433 reviews)
"Pretty landscape all around"
United States
Karen B
The price is €84
includes taxes & fees
19 Oct - 20 Oct
Brittany Motel
A hotel room with two beds, a desk, a chair, a mirror, a TV, and a window with curtains.

11. Royal Inn Claremont

Royal Inn Claremont
2.0 star property
Claremont
6.8 out of 10, (362 reviews)
"My room was immaculate. I was pleasantly surprised with all the amenities, including a refrigerator and microwave. The only thing that I would have liked to have was a robe hook on the bathroom door. Other than that it was perfect !"
United States
Bonita
The price is €105
includes taxes & fees
1 Nov - 2 Nov
Royal Inn Claremont
A modern hotel lobby with a wooden herringbone floor, a green wall with 'Chalet 289' signage, a bench with white cushions, and a reception desk with a trash bin and storage baskets.

12. Chalet 239

Chalet 239
2.0 star property
West Dover
9.4 out of 10, Exceptional, (154 reviews)
"We enjoyed staying the night during a road trip - very comfortable with welcoming staff."
United States
Ruth
The price is €151
includes taxes & fees
1 Nov - 2 Nov
Chalet 239
A mountain with autumn foliage and a bridge in the foreground.

13. Aerie Inn of Vermont

Aerie Inn of Vermont
2.0 star property
East Dorset
9.4 out of 10, Exceptional, (192 reviews)
"The Aerie Inn was clean and cozy. We were very comfortable and would visit again."
United States
Paige
The price is €123
includes taxes & fees
25 Oct - 26 Oct
Aerie Inn of Vermont
A reception area with a counter, a computer, and various informational posters on the wall.

14. Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT
2.5 star property
Brattleboro
6.0 out of 10, (819 reviews)
"Room was in excellent condition , very Clean The vanity and sink on Room was very helpful Parking was a easy View to the mountain was beautiful"
United States
Nicolas
The price is €84
includes taxes & fees
4 Nov - 5 Nov
Travelodge by Wyndham Brattleboro VT
A cozy living room with a fireplace, a coffee station, and a view of the outside.

15. Colonial Motel

Colonial Motel
3.0 star property
Brattleboro
6.2 out of 10, (87 reviews)
"very convenient and cost was good, as we stay in Brattleboro as our daughter and granddaughter live in Turners Falls Mass. and its only a half hour drive to visit with them."
United States
Leonard
The price is €88
includes taxes & fees
1 Nov - 2 Nov
Colonial Motel
A stone fountain surrounded by rocks, with a house in the background.

16. Weathervane Motel

Weathervane Motel
2.0 star property
Manchester Center
6.8 out of 10, (808 reviews)
"Loved the fireplace"
United States
James
The price is €95
includes taxes & fees
12 Oct - 13 Oct
Weathervane Motel
A swimming pool area with lounge chairs and a sunbed, surrounded by windows and doors.

17. Econo Lodge Brattleboro South

Econo Lodge Brattleboro South
2.0 star property
Brattleboro
5.2 out of 10, (685 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 €98
includes taxes & fees
10 Nov - 11 Nov
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.
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Top Chester Hotel Reviews

The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

8/10 Good
"Nice clean rooms comfortable, breakfast was a nice way to start today."
Alain 2-night trip
Posted less than an hour ago
The Black Bear Lodge at Stratton Mountain Resort

Find out more about Chester

Chester Motels information

Number of reviews
5,793
Accommodation
24 Motels
Lowest Price
€83
Highest Price
€200

Frequently asked questions

What can I expect from a motel trip to Chester?
If you're not able to find a motel in Chester, consider some of the motels we suggest around the area or let Expedia help you find a similar property from over 67 hotels and other accommodation options. Simply filter using our search tools by price per night or money-saving amenities such as free parking and free breakfast.
What are motels like?
At most motels, you'll often find an outdoor pool and free parking. When you stay at a motel, you'll usually access your room directly from the car park. The word "motel" was conceived 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' favourite motels to book 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 self-parking. Colonial Motel: A 24-hour front desk along with freebies such as breakfast, WiFi and self-parking are available during your stay. Central Chester is 26.6 mi (42.8 km) away. The Putney Inn: Enjoy access to the 24-hour front desk, and freebies including breakfast, WiFi and self-parking. Located 21 mi (33.8 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 such as 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 self-parking.
What things can I to do in Chester?
As you explore this relaxing, quaint area, explore the ski slopes. Visitors like Chester for its shops, coffee shops 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 exploring 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 road trip, 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 temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chester are January, March, November and February, with each month seeing an average of 35 cm of snowfall.
What are my options for getting around Chester while 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) away. You can also search for flights into 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 to rent a car for your trip.