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Check prices for these dates

Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct
In one month
23 Oct - 25 Oct
In two months
20 Nov - 22 Nov

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 NZ$167
includes taxes & fees
27 Sept - 28 Sept
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, (585 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 NZ$214
includes taxes & fees
27 Sept - 28 Sept
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, (221 reviews)
"Clean, modern, and peaceful."
Canada
Omar
The price is NZ$247
includes taxes & fees
28 Sept - 29 Sept
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, (357 reviews)
"I like it was clean bathroom was new."
United States
Eva
The price is NZ$230
includes taxes & fees
28 Sept - 29 Sept
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, (190 reviews)
"Everything was welcoming from check in to check out. Room was clean and spacious. Property is beautiful if you just wanted to veg outdoors. It’s fairly close to Manchester and apple picking is right down the road. If I were to be in the area again, I would definitely stay here again."
United States
Marianne
The price is NZ$210
includes taxes & fees
28 Sept - 29 Sept
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 NZ$395
includes taxes & fees
26 Sept - 27 Sept
COHO Inn & Motor Lodge
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".

7. Main and Mountain Bar & Motel

Main and Mountain Bar & Motel
2.0 star property
Ludlow
9.6 out of 10, Exceptional, (229 reviews)
"Comfy beds , great shower and awesome coffee room !"
United States
Kristina
The price is NZ$492
includes taxes & fees
30 Sept - 1 Oct
Main and Mountain Bar & Motel
A sign for The Putney Inn, a restaurant and motel, with a friendly welcome message and floral decorations.

8. The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1,002 reviews)
"Clean room, staff, breakfast, and parking were great!"
United States
JANE
The price is NZ$163
includes taxes & fees
25 Oct - 26 Oct
The Putney Inn
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 NZ$167
includes taxes & fees
20 Oct - 21 Oct
Brittany Motel
A spacious kitchen with wooden cabinets, a large island, and a dining area with floral tablecloths.

10. Four Winds Country Motel

Four Winds Country Motel
2.0 star property
Manchester Center
8.4 out of 10, Very good, (561 reviews)
"Partially updated. Still needs some adjustments but it was clean and comfortable. Breakfast was good."
United States
Catharina
The price is NZ$242
includes taxes & fees
26 Oct - 27 Oct
Four Winds Country Motel
A modern kitchen with a central island, stainless steel appliances, and a dining area with chairs.

11. Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (623 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 NZ$259
includes taxes & fees
27 Sept - 28 Sept
Sleep Woodstock 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.

12. 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 NZ$387
includes taxes & fees
26 Sept - 27 Sept
The Olympia Lodge
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.

13. 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 NZ$221
includes taxes & fees
4 Oct - 5 Oct
Chalet 239
A cozy living room with a fireplace, a coffee station, and a view of the outside.

14. Colonial Motel

Colonial Motel
3.0 star property
Brattleboro
6.6 out of 10, (65 reviews)
"The room was substantially larger than most motels provide. It was quiet, bed was comfortable. Location was convenient, easy to find and agreeable. Breakfast was very limited— coffee, tea, toast, bagel. Overall, I would stay there again."
Canada
Alida
The price is NZ$162
includes taxes & fees
27 Sept - 28 Sept
Colonial Motel
A stone fountain surrounded by rocks, with a house in the background.

15. Weathervane Motel

Weathervane Motel
2.0 star property
Manchester Center
6.8 out of 10, (804 reviews)
"Loved the fireplace"
United States
James
The price is NZ$208
includes taxes & fees
27 Sept - 28 Sept
Weathervane Motel
A reception area with a counter, a computer, and various informational posters on the wall.

16. Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT
2.5 star property
Brattleboro
6.0 out of 10, (807 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 NZ$122
includes taxes & fees
28 Sept - 29 Sept
Travelodge by Wyndham Brattleboro VT
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, (681 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 NZ$193
includes taxes & fees
25 Oct - 26 Oct
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 Shire Woodstock

The Shire Woodstock

10/10 Excellent
"Great views"
J R 4-night trip
Posted 4 hours ago
The Shire Woodstock

Find out more about Chester

Chester Motels information

Number of reviews
6,051
Accommodation
24 Motels
Lowest Price
NZ$122
Highest Price
NZ$492

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 66 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. 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. Claremont Motor Lodge: 14.7 mi (23.7 km) from the heart of Chester. Enjoy access to the free Wi-Fi and free parking, as well as room amenities such as air conditioning.
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 Bonnie's Bundles Dolls and DaVallia Art & Accents. 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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