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Check prices for these dates

Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18
In one month
Oct 30 - Nov 1
In two months
Nov 27 - Nov 29

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, (707 reviews)
"Very nice staff easy access to everything good for dogs clean pool"
United States
Terry
The price is P6,256
P7,163 total
includes taxes & fees
Oct 27 - Oct 28
The Upper Pass Lodge at Magic Mountain
A hotel room with two beds, a wooden headboard, bedside lamps, and a window with curtains.

2. Claremont Motor Lodge

Claremont Motor Lodge
2.5 star property
Claremont
8.8 out of 10, Excellent, (589 reviews)
"The manager was great, room was very clean and the bed was great. It’s an older motor inn but the manager takes pride in the whole Inn."
United States
Jerri
The price is P7,510
P8,148 total
includes taxes & fees
Oct 18 - Oct 19
Claremont Motor Lodge
A modern bedroom with two beds, wooden headboards, a bench, a small table, and a large window with a view of greenery.

3. Otherland Hotel

Otherland Hotel
2.5 star property
Newfane
9.6 out of 10, Exceptional, (222 reviews)
"Clean, modern, and peaceful."
Canada
Omar
The price is P8,926
P11,707 total
includes taxes & fees
Oct 1 - Oct 2
Otherland Hotel
A hotel room with two beds, a desk, a chair, a mirror, a TV, and a window with curtains.

4. Royal Inn Claremont

Royal Inn Claremont
2.0 star property
Claremont
6.8 out of 10, (360 reviews)
"I like it was clean bathroom was new."
United States
Eva
The price is P8,730
P9,472 total
includes taxes & fees
Oct 1 - Oct 2
Royal Inn Claremont
A mountain with autumn foliage and a bridge in the foreground.

5. Aerie Inn of Vermont

Aerie Inn of Vermont
2.0 star property
East Dorset
9.4 out of 10, Exceptional, (191 reviews)
"Nice location and beautiful spot. Great service and very yummy coffee in the morning. Thanks so much!"
United States
Catherine B
The price is P7,430
P8,099 total
includes taxes & fees
Oct 1 - Oct 2
Aerie Inn of Vermont
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.

6. 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 P14,532
P15,840 total
includes taxes & fees
Oct 14 - Oct 15
COHO Inn & Motor Lodge
A sign for The Putney Inn, a restaurant and motel, with a friendly welcome message and floral decorations.

7. The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1,002 reviews)
"Safe and relaxing"
United States
Elizabeth G
The price is P5,266
P5,793 total
includes taxes & fees
Oct 25 - Oct 26
The Putney Inn
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".

8. 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 P16,373
P18,011 total
includes taxes & fees
Oct 6 - Oct 7
Main and Mountain Bar & Motel
A spacious living area with a high ceiling, a wooden staircase, and a built-in kitchen visible through an open door.

9. Brittany Motel

Brittany Motel
2.0 star property
Manchester Center
9.4 out of 10, Exceptional, (427 reviews)
"Very nice setup for a solo traveler. Would be tight for a couple."
United States
Robert
The price is P5,382
P5,920 total
includes taxes & fees
Oct 20 - Oct 21
Brittany Motel
A modern kitchen with a central island, stainless steel appliances, and a dining area with chairs.

10. Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (625 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 P8,280
P9,108 total
includes taxes & fees
Oct 27 - Oct 28
Sleep Woodstock Motel
A spacious kitchen with wooden cabinets, a large island, and a dining area with floral tablecloths.

11. Four Winds Country Motel

Four Winds Country Motel
2.0 star property
Manchester Center
8.4 out of 10, Very good, (562 reviews)
"Partially updated. Still needs some adjustments but it was clean and comfortable. Breakfast was good."
United States
Catharina
The price is P8,392
P9,231 total
includes taxes & fees
Oct 25 - Oct 26
Four Winds Country Motel
A cozy living room with a fireplace, a coffee station, and a view of the outside.

12. Colonial Motel

Colonial Motel
3.0 star property
Brattleboro
6.6 out of 10, (70 reviews)
"Staff was very helpful. A little seating area under some trees was a beautiful place to relax while the sun was setting."
United States
Sondra
The price is P6,308
P6,939 total
includes taxes & fees
Oct 1 - Oct 2
Colonial Motel
A reception area with a counter, a computer, and various informational posters on the wall.

13. Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT
2.5 star property
Brattleboro
6.0 out of 10, (809 reviews)
"Nice staff."
United States
Donna
The price is P3,943
P4,337 total
includes taxes & fees
Oct 5 - Oct 6
Travelodge by Wyndham Brattleboro VT
A stone fountain surrounded by rocks, with a house in the background.

14. Weathervane Motel

Weathervane Motel
2.0 star property
Manchester Center
6.8 out of 10, (806 reviews)
"Loved the fireplace"
United States
James
The price is P6,698
P7,368 total
includes taxes & fees
Oct 4 - Oct 5
Weathervane Motel
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.

15. Chalet 239

Chalet 239
2.0 star property
West Dover
9.4 out of 10, Exceptional, (148 reviews)
"We enjoyed staying the night during a road trip - very comfortable with welcoming staff."
United States
Ruth
The price is P8,756
P9,632 total
includes taxes & fees
Oct 4 - Oct 5
Chalet 239
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.

16. The Olympia Lodge

The Olympia Lodge
2.5 star property
Manchester Center
9.4 out of 10, Exceptional, (607 reviews)
"amazing breakfast!"
United States
Matheus
The price is P14,043
P15,448 total
includes taxes & fees
Oct 23 - Oct 24
The Olympia Lodge
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, (682 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 P6,224
P6,846 total
includes taxes & fees
Oct 29 - Oct 30
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

On The River Inn

On The River Inn

10/10 Excellent
"Loved the all in one dining room, bar, lounge area with fireplace Excellent swordfish dinner"
Kathryn 1-night trip
Posted 1 hour ago
On The River Inn

Find out more about Chester

Chester Motels information

Number of reviews
6,857
Accommodation
24 Motels
Lowest Price
P4,337
Highest Price
P18,011

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: 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. 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. 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 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, 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.

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