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Check prices for these dates

Next weekend
6 Nov - 8 Nov
In two weeks
13 Nov - 15 Nov
In one month
27 Nov - 29 Nov
In two months
25 Dec - 27 Dec

Our top choices for Chester motels

A two-story building with a red facade, a balcony on the second floor, and a parking lot in front.

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, (713 reviews)
"Beds and bedding were super comfy but the room itself was rather small and dated."
United States
Lynne
The price is S$134
includes taxes & fees
28 Oct - 29 Oct
The Upper Pass Lodge at Magic Mountain
A sign for The Putney Inn, a restaurant and motel, with a friendly welcome message and floral decorations.

2. The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1,003 reviews)
"Great location and wonderful staff! I love staying here every year!"
United States
Kristen
The price is S$111
includes taxes & fees
26 Nov - 27 Nov
The Putney Inn
A modern kitchen with a central island, stainless steel appliances, and a dining area with chairs.

3. Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (644 reviews)
"This hotel was such a nice surprise! The room was very clean and decorated nicely! Super quiet A/C units and a short drive to town."
Canada
Dave
The price is S$109
includes taxes & fees
27 Oct - 28 Oct
Sleep Woodstock Motel
A spacious living area with a high ceiling, a wooden staircase, and a built-in kitchen visible through an open door.

4. Brittany Motel

Brittany Motel
2.0 star property
Manchester Center
9.2 out of 10, Wonderful, (449 reviews)
"It was a great stay"
United States
Keith
The price is S$121
includes taxes & fees
28 Oct - 29 Oct
Brittany Motel
A hotel room with two beds, a wooden headboard, bedside lamps, and a window with curtains.

5. Claremont Motor Lodge

Claremont Motor Lodge
2.5 star property
Claremont
8.8 out of 10, Excellent, (604 reviews)
"Very nice stay! The place doesn't look that great from the road, but the room was super comfortable, very clean and spacious. And the staff was very nice. The town of Claremont was a treat: very friendly and community-oriented. We would definitely return to Claremont and the Motor Lodge when we are back in the area."
United States
Marguerite
The price is S$153
includes taxes & fees
17 Nov - 18 Nov
Claremont Motor Lodge
A modern outdoor lounge area with two lounge chairs and a wooden deck.

6. Otherland Hotel

Otherland Hotel
2.5 star property
Newfane
9.6 out of 10, Exceptional, (232 reviews)
"Love the Nordik style accommodations and very comfortable bed!"
United States
Debi
The price is S$217
includes taxes & fees
27 Oct - 28 Oct
Otherland Hotel
A reception area with a counter, a computer, and various informational posters on the wall.

7. Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT
2.5 star property
Brattleboro
6.0 out of 10, (833 reviews)
"Great value! Older facility, smaller room and beds but perfect for our stay which basically only involved using the room to sleep."
United States
Stephen
The price is S$87
includes taxes & fees
27 Oct - 28 Oct
Travelodge by Wyndham Brattleboro VT
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.

8. COHO Inn & Motor Lodge

COHO Inn & Motor Lodge
2.0 star property
Weston
9.4 out of 10, Exceptional, (79 reviews)
"Quiet and peaceful."
United States
James
The price is S$286
includes taxes & fees
27 Oct - 28 Oct
COHO Inn & Motor Lodge
An air conditioner with a control panel displaying temperature settings.

9. 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 S$147
includes taxes & fees
26 Nov - 27 Nov
Royal Inn Claremont
A mountain with autumn foliage and a bridge in the foreground.

10. Aerie Inn of Vermont

Aerie Inn of Vermont
2.0 star property
East Dorset
9.4 out of 10, Exceptional, (201 reviews)
"Just a lovely little Motel, very nice people."
United States
Chris
The price is S$176
includes taxes & fees
27 Oct - 28 Oct
Aerie Inn of Vermont
A cozy cabin interior with a fireplace, wooden walls, a checkered chair, and a large window allowing natural light.

11. Four Winds Country Motel

Four Winds Country Motel
2.0 star property
Manchester Center
8.4 out of 10, Very good, (578 reviews)
"The staff was friendly and helpful. The rooms were newly renovated with a contemporary tile bathroom and new beds. This was an older motel that has all been redone inside."
United States
Mary Ellen
The price is S$142
includes taxes & fees
26 Nov - 27 Nov
Four Winds Country Motel
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".

12. Main and Mountain Bar & Motel

Main and Mountain Bar & Motel
2.0 star property
Ludlow
9.6 out of 10, Exceptional, (233 reviews)
"Comfortable and clean property. Nicely appointed and well maintained. Great shower, comfy bed. Would stay again. And eat breakfast at the nearby Hatchery!"
United States
David
The price is S$368
includes taxes & fees
16 Nov - 17 Nov
Main and Mountain Bar & Motel
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.

13. The Olympia Lodge

The Olympia Lodge
2.5 star property
Manchester Center
9.4 out of 10, Exceptional, (623 reviews)
"Cute family run lodge with excellent made to order breakfast."
United States
Ivy
The price is S$281
includes taxes & fees
30 Oct - 31 Oct
The Olympia Lodge
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, (813 reviews)
"The motel looked a little old, tired, but the room was very clean and spacious, moderately priced, and very close to town. The staff was busy but helped immediately."
United States
Sallie
The price is S$136
includes taxes & fees
27 Oct - 28 Oct
Weathervane Motel
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
6.4 out of 10, (108 reviews)
"Value for money. Clean and conveniently located. Friendly staff."
United States
Swaraj
The price is S$120
includes taxes & fees
3 Nov - 4 Nov
Colonial Motel
A swimming pool area with lounge chairs and a sunbed, surrounded by windows and doors.

16. Econo Lodge Brattleboro South

Econo Lodge Brattleboro South
2.0 star property
Brattleboro
5.2 out of 10, (692 reviews)
"I asked him on the front desk if I get a coffee machine but hi said no wen i order online they said breakfast is available but is not the guy in front desk was rude"
United States
Luis
The price is S$140
includes taxes & fees
24 Nov - 25 Nov
Econo Lodge Brattleboro South
A wooden deck with a bench and an umbrella, leading to a dark-colored building with a door and windows.

17. Chalet 239

Chalet 239
2.0 star property
West Dover
9.4 out of 10, Exceptional, (157 reviews)
"We enjoyed staying the night during a road trip - very comfortable with welcoming staff."
United States
Ruth
The price is S$216
includes taxes & fees
1 Nov - 2 Nov
Chalet 239
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 Shire Woodstock

The Shire Woodstock

8/10 Good
"Loved the location and room. Bed mattress was not great."
Tim 2-night trip
Posted 1 hour ago
The Shire Woodstock

Find out more about Chester

Chester Motels information

Number of reviews
5,332
Accommodation
24 Motels
Lowest Price
S$87
Highest Price
S$368

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.

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