Accommodations in Chester (Page 3)

Enjoy your stay and find the best accommodations in Chester at affordable prices

Searching for an accommodation in Chester (Massachusetts)? You will find a various number of lodgings for your overnight stay in Chester, starting from $45 per bed and night. Whether you are looking for a hotel, a guesthouse or an apartment, you will find an accommodation that meets your needs.

Accommodations in Chester and region (40 miles)

Stockbridge Home Walk to Town Beach!

Holiday home in Stockbridge near Chester, Massachusetts

Stockbridge Home - Walk to Lakefront Beach! is situated in Stockbridge, 3.9 km from Tanglewood, 5.7 km from Cranwell Spa & Golf Club, and 6.5 km from ...

Parking

no reviews

from $272.33 Show details »

Cozy Great Barrington Home about 1 Mi to...

Holiday home in Great Barrington near Chester, Massachusetts

Located in Great Barrington, 18 km from Norman Rockwell Museum, 22 km from Cranwell Spa & Golf Club and 23 km from Tanglewood Musical Center, Cozy Gre...

Parking

Very good 2 Reviews 8.5

from $488.67 Show details »

Apple Tree Inn

Inn in Lenox near Chester, Massachusetts , 10 Richmond Mountain Road

Situated in Lenox, 1.1 km from Tanglewood Musical Center, Apple Tree Inn features accommodation with a seasonal outdoor swimming pool, free private pa...

Parking
Restaurant
Bar
Family rooms
Outdoor pool

Good 339 Reviews 7.8

from $259.00 Show details »

The Hotel Northampton

Hotel in Northampton near Chester, Massachusetts , 36 King St.

Set in Northampton, 12 km from Amherst College, The Hotel Northampton offers accommodation with a fitness centre, free private parking, a terrace and ...

Parking
Restaurant
Bar
Fitness centre
Kid meals

Very good 411 Reviews 8.5

from $195.99 Show details »

North King Motel

Motel in Northampton near Chester, Massachusetts , 504 North King Street

Situated in Northampton, within 13 km of Amherst College and 37 km of Eastern States Exposition Center, North King Motel features accommodation with a...

Parking

Good 315 Reviews 7.3

from $81.67 Show details »

Fairfield Inn & Suites by Marriott Sprin...

Hotel in Northampton near Chester, Massachusetts , 115A Conz Street

Featuring an indoor pool and a fitness centre, Fairfield Inn & Suites by Marriott Springfield Northampton/Amherst is located in Northampton.

Bar
Allergy-free room
Air conditioning
Hairdryer
Iron

Fabulous 242 Reviews 8.7

from $221.86 Show details »

The Central Downtown Inn Suites

Hotel in Pittsfield near Chester, Massachusetts , 20 West Housatonic Street

Offering suites with a deck or patio, this hotel is located in the heart of the Pittsfield city centre, walking distance from numerous shops and resta...

Parking
Pets allowed

Superb 71 Reviews 9.1

from $129.99 Show details »

Holiday Inn & Suites Pittsfield-Berkshir...

Hotel in Pittsfield near Chester, Massachusetts , 1 West Street

Next to the Beacon Cinema in Pittsfield, Massachusetts, this hotel offers guestrooms with free wired internet access and coffeemakers as well as an on...

Restaurant
Pets allowed
Bar
Fitness centre
Spa and wellness centre

Good 285 Reviews 7.4

from $151.20 Show details »

The Briarcliff Motel

Motel in Great Barrington near Chester, Massachusetts , 506 Stockbridge Road

Surrounded by the Berkshires, this motel is 8 km from Ski Butternut and boasts free Wi-Fi access and views of Monument Mountain.

Parking
Pets allowed
Kids' outdoor play equipment
Shower
TV

Good 219 Reviews 7.6

from $175.00 Show details »

Berkshire Inn

Motel in Pittsfield near Chester, Massachusetts , 150 West Housatonic Street

Located in the heart of the Berkshire Mountains, this family-owned motel features an outdoor pool and free Wi-Fi.

Parking
Family rooms
Outdoor pool
Swimming pool
Swimming Pool

Good 417 Reviews 7.3

from $99.99 Show details »

Hotel on North

Hotel in Pittsfield near Chester, Massachusetts , 297 North Street

Situated in Pittsfield and within 13 km of Tanglewood, Hotel on North has a bar, non-smoking rooms, and free WiFi throughout the property.

Parking
Pets allowed
Bar
Family rooms
Breakfast in the room

Superb 189 Reviews 9.0

from $245.33 Show details »

Hatfield Inn

Motel in Hatfield near Chester, Massachusetts , 20 West Street

Located just off of Interstate 91 in Hatsfield, Massachusetts, Scottish Inns is within 20 minutes’ drive of Amherst College and the University of Ma...

Parking
Bath
TV
Air conditioning
Desk

Disappointing 305 Reviews 4.9

from $87.00 Show details »

Fairfield Inn & Suites by Marriott Sprin...

Hotel in Holyoke near Chester, Massachusetts , 229 Whiting Farms Road

Set in Holyoke, 12 km from Eastern States Exposition Center, Fairfield Inn & Suites by Marriott Springfield Holyoke offers accommodation with a fitnes...

Parking
Fitness centre
Family rooms
Allergy-free room
Indoor pool

Fabulous 179 Reviews 8.9

from $127.00 Show details »

Homewood Suites by Hilton Holyoke-Spring...

Hotel in Holyoke near Chester, Massachusetts , 375 Whitney Avenue

Adjacent to the Holyoke Mall and easily accessible from Interstate 91, this Massachusetts hotel features spacious all-suite accommodations, complete w...

Parking
Pets allowed
Fitness centre
Family rooms
Indoor pool

Very good 222 Reviews 8.6

from $147.55 Show details »

Tranquil 3 BR Stockbridge House with Pri...

Holiday home in Stockbridge near Chester, Massachusetts

Tranquil 3BR Stockbridge House with Private Deck! is situated in Stockbridge, 8.5 km from Tanglewood Musical Center, 9.1 km from Tanglewood, and 14 km...

Parking
Pets allowed
Internet facilities
Hairdryer
Iron

Superb 2 Reviews 9.5

from $416.00 Show details »

The Mill River Cabin with Fireplace and...

Holiday home in Mill River near Chester, Massachusetts

The Mill River Cabin with Fireplace and River View! is situated in Mill River, 30 km from Norman Rockwell Museum, 35 km from Cranwell Spa & Golf Club,...

Parking
Pets allowed
Internet facilities
Hairdryer
Toilet

Superb 4 Reviews 9.5

from $244.33 Show details »

Thornewood Inn

Inn in Great Barrington near Chester, Massachusetts , 453 Stockbridge Road

Great Barrington’s Thornewood Inn is a bed and breakfast that features antique furniture throughout the property.

Parking
Pets allowed
Bar
Family rooms
Outdoor pool

Good 18 Reviews 8.0

from $249.00 Show details »

D. Hotel Suites & Spa

Hotel in Holyoke near Chester, Massachusetts , 1 Country Club Road

Located near Interstate 91, this Holyoke hotel offers free WiFi and rooms equipped with cable TV.

Parking
Restaurant
Bar
Fitness centre
Family rooms

Fabulous 861 Reviews 8.7

from $136.15 Show details »

Travelodge by Wyndham Great Barrington B...

Motel in Great Barrington near Chester, Massachusetts , 400 Stockbridge Road

Situated only 5 miles from Stockbridge & Norman Rockwell, this hotel is set in a convenient location in Great Barrington.

Parking
Family rooms
Outdoor pool
Swimming pool
Swimming Pool

Pleasant 196 Reviews 6.9

from $100.50 Show details »

Holiday Inn Express Great Barrington, an...

Hotel in Great Barrington near Chester, Massachusetts , 415 Stockbridge Road

Located in the Southern Berkshire Mountains, this hotel boasts an indoor pool and hot tub, as well as a daily continental breakfast.

Parking
Fitness centre
Allergy-free room
Indoor pool
Swimming pool

Very good 287 Reviews 8.2

from $185.57 Show details »

Fairfield Inn & Suites by Marriott Great...

Hotel in Great Barrington near Chester, Massachusetts , 249 Stockbridge Road

The 100 percent non-smoking Fairfield Inn and Suites by Marriott is located in the heart of the Berkshires.

Parking
Fitness centre
Allergy-free room
Kids' outdoor play equipment
Kid-friendly buffet

Fabulous 184 Reviews 8.8

from $237.00 Show details »

Monument Mountain Motel

Motel in Great Barrington near Chester, Massachusetts , 247 Stockbridge Road

This Great Barrington motel features free Wi-Fi and rooms with a microwave and a refrigerator.

Parking

Very good 202 Reviews 8.0

from $130.00 Show details »

Hampton Inn Hadley-Amherst Area

Hotel in Hadley near Chester, Massachusetts , 24 Bay Road

Just off Interstate 91 and close to area points of interest, including Amherst College, this hotel offers comfortable guest accommodations and many fr...

Parking
Pets allowed
Fitness centre
Indoor pool
Swimming pool

Very good 246 Reviews 8.4

from $152.24 Show details »

Pleasant Valley Motel West Stockbridge

Motel in West Stockbridge near Chester, Massachusetts , 42 Stockbridge Road

Situated in West Stockbridge, 5.5 km from Norman Rockwell Museum, Pleasant Valley Motel West Stockbridge features accommodation with free WiFi and fre...

Parking
Shower
Bath
TV
Air conditioning

Okay 126 Reviews 5.8

from $69.52 Show details »

Granville House

B&B in Great Barrington near Chester, Massachusetts , 98 Division Street

Situated in Great Barrington in the Massachusetts region, Granville House features accommodation with free private parking.

Parking
Pets allowed
Family rooms

Exceptional 131 Reviews 9.9

from $275.00 Show details »

Number of Accommodations in Chester	201
Average price per night	$146.79
Lowest price per night	$45.00
Highest price per night	$995.00

Most popular accommodations in Chester

The most popular accommodations in Chester based on average guest rating (Top 10).

Cheapest accommodations in Chester

The cheapest accommodations in Chester based on room rate per night (Top 10).

Most booked accommodations in Chester

The most booked accommodations in Chester based on popularity with guests (Top 10).

Sleep & Travel in Chester (Massachusetts)

Getting the best travel and overnight stay experience requires careful planning and attention to detail. Start by researching your destination and choosing the right accommodations for your needs and budget. Consider factors such as location, amenities, and reviews from other travelers. To make the most of your trip, take the time to explore Chester and immerse yourself in the local culture. This might include trying new foods, visiting historic sites, or attending cultural events.

When booking your accommodation in Chester, be sure to communicate any special requests or preferences you may have, such as a specific room type or dietary restrictions. This will help ensure that your stay is comfortable and enjoyable. Also don't forget to pack wisely and bring along any necessary travel essentials, such as comfortable shoes, sunscreen, and a camera to capture all of your memories. With careful planning and a spirit of adventure, you can have an unforgettable travel and overnight stay experience.

How to find the best accommodation in Chester

To find the perfect place to stay in Chester, consider your budget, preferred location, and the amenities you need. Do you want to stay in a hotel or a vacation rental or do your prefer an apartment or house with more space, privacy, and the opportunity to live like a local? Do you need access to a kitchen, laundry facilities, or a gym? Research online reviews and ratings to get an idea of what past guests have experienced. Also, consider the type of trip you're taking. If you're traveling with family, you may need a larger space or a kid-friendly environment. If you're on a romantic getaway, you may want a more intimate setting.

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