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Check prices for these dates

Next weekend
15 May - 17 May
In two weeks
22 May - 24 May
In one month
5 Jun - 7 Jun
In two months
3 Jul - 5 Jul

Our top choices for Chester motels

Signature Suite, Kitchen, Mountain View | Living area | 42-inch TV with cable channels

Brittany Motel

Brittany Motel
2.0 star property
Manchester Center
9.4 out of 10, Exceptional, (352 reviews)
"I love this place! It’s funky and kind. Kept clean and just has a really inviting and sweet vibe."
United States
Andrew
The price is AED 275
AED 303 total
includes taxes & fees
11 May - 12 May
Brittany Motel
Deluxe Suite | Private kitchen | Mini-fridge, microwave, coffee/tea maker, freezer

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (576 reviews)
"Quiet, well kept, comfortable, convenient."
United States
Elisabeth
The price is AED 249
AED 483 total
includes taxes & fees
14 May - 15 May
Sleep Woodstock Motel
Room, 2 Queen Beds, Non Smoking, Refrigerator & Microwave | Premium bedding, in-room safe, individually decorated

Claremont Motor Lodge

Claremont Motor Lodge
2.5 star property
Claremont
8.8 out of 10, Excellent, (499 reviews)
"Convenient location and friendly staff."
United States
Robert
The price is AED 338
AED 367 total
includes taxes & fees
10 May - 11 May
Claremont Motor Lodge
Mountain view

Aerie Inn of Vermont

Aerie Inn of Vermont
2.0 star property
East Dorset
9.4 out of 10, Exceptional, (180 reviews)
"Very comfortable room and nice staff. Will stay there again. "
United States
Laura
The price is AED 465
AED 506 total
includes taxes & fees
14 May - 15 May
Aerie Inn of Vermont
Exterior

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very Good, (1,002 reviews)
"Pleasant stay!"
United States
Steven
The price is AED 345
AED 380 total
includes taxes & fees
13 May - 14 May
The Putney Inn
Lobby sitting area

Chalet 239

Chalet 239
2.0 star property
West Dover
9.4 out of 10, Exceptional, (125 reviews)
"Great stay "
United States
Jean
The price is AED 390
AED 429 total
includes taxes & fees
17 May - 18 May
Chalet 239
Restaurant

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, (700 reviews)
"Charming rustic inn. Staff were delightful and food was great. "
United States
Bradley
The price is AED 404
AED 448 total
includes taxes & fees
7 Jun - 8 Jun
The Upper Pass Lodge at Magic Mountain
Standard Room, 2 Double Beds | Desk, blackout drapes, iron/ironing board, free WiFi

Royal Inn Claremont

Royal Inn Claremont
2.0 star property
Claremont
6.6 out of 10, (337 reviews)
"You can’t go wrong with the price. Close to many activities."
United States
Carolina
The price is AED 367
AED 399 total
includes taxes & fees
10 May - 11 May
Royal Inn Claremont
Free continental breakfast on weekends

Four Winds Country Motel

Four Winds Country Motel
2.0 star property
Manchester Center
8.4 out of 10, Very Good, (545 reviews)
"Clean room, friendly staff. "
United States
Ken
The price is AED 400
AED 440 total
includes taxes & fees
11 May - 12 May
Four Winds Country Motel
Front of property

COHO Inn & Motor Lodge

COHO Inn & Motor Lodge
2.0 star property
Weston
9.4 out of 10, Exceptional, (74 reviews)
"Good place to stay. "
United States
steven
The price is AED 645
AED 703 total
includes taxes & fees
11 May - 12 May
COHO Inn & Motor Lodge
Reception

Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT
2.5 star property
Brattleboro
6.0 out of 10, (769 reviews)
"It was fairly clean room was cold however the staff was amazing, Awesome Customer Service skills and flexibility to accommodate my needs. I will definitely recommend to others. "
United States
Vivian
The price is AED 281
AED 309 total
includes taxes & fees
12 May - 13 May
Travelodge by Wyndham Brattleboro VT
Interior

The Olympia Lodge

The Olympia Lodge
2.5 star property
Manchester Center
9.4 out of 10, Exceptional, (588 reviews)
"Clean comfortable room, nice owner and good breakfast."
United States
Marc
The price is AED 694
AED 764 total
includes taxes & fees
25 May - 26 May
The Olympia Lodge
Fountain

Weathervane Motel

Weathervane Motel
2.0 star property
Manchester Center
6.8 out of 10, (765 reviews)
"Courteous staff and clean rooms. "
United States
Andrew
The price is AED 393
AED 433 total
includes taxes & fees
10 May - 11 May
Weathervane Motel
Front of property - evening/night

Main and Mountain Bar & Motel

Main and Mountain Bar & Motel
2.0 star property
Ludlow
9.6 out of 10, Exceptional, (221 reviews)
"Overall great property and stay!"
United States
Cassondra
The price is AED 708
AED 779 total
includes taxes & fees
1 Jun - 2 Jun
Main and Mountain Bar & Motel
Breakfast area

Rodeway Inn Bellows Falls

Rodeway Inn Bellows Falls
2.0 star property
Bellows Falls
6.2 out of 10, (291 reviews)
"room was very neat, staff very polite, TV & WiFi could be better "
United States
Timothy
The price is AED 403
AED 439 total
includes taxes & fees
7 Jun - 8 Jun
Rodeway Inn Bellows Falls
Seasonal outdoor pool

Econo Lodge Brattleboro South

Econo Lodge Brattleboro South
2.0 star property
Brattleboro
5.4 out of 10, (635 reviews)
"Near food and shopping, ac and heater work good."
United States
Juan
The price is AED 261
AED 287 total
includes taxes & fees
28 May - 29 May
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

Latchis Hotel

Latchis Hotel

10/10 Excellent
"Really great place to stay in Brattleboro. Clean room, friendly and helpful staff, free coffee in the lobby and a great little bar/restaurant is attached. I'll definitely be back."
Kaitlin 3-night trip
Posted 2 hours ago
Latchis Hotel

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 66 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: If driving, you'll be within 26 minutes of Okemo Mountain Resort. Enjoy the in-room free WiFi, and freebies including breakfast and parking. Colonial Motel And Spa: 2 indoor pools, a full-service spa, and free WiFi 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. Brittany Motel: Central Chester is 26.7 mi (42.9 km) away. Free WiFi, free parking, and a snack bar/deli are available during your stay. Econo Lodge Brattleboro South: 29.4 mi (47.3 km) from the heart of Chester. Enjoy access to the seasonal outdoor pool, and freebies including breakfast, 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 North Springfield Lake Recreation Area, Lowell Lake State Park, and Saxtons River Recreation Area. 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, The Nature Museum, and Magic Mountain Ski Resort.
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.