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Accommodations in Chester

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)
Historic Huntington Home - Walk to Westfield River in Huntington, USA

Historic Huntington Home - Walk to Westf...

Holiday home in Huntington near Chester, Massachusetts
Located in Huntington in the Massachusetts region, Historic Huntington Home - Walk to Westfield River has a patio and garden views.
  • Parking

Fabulous 1 Reviews 9.0

from $357.00 Show details »

Berkshires Home on 11 Acres with Pond and 2 Fire Pits! in Becket, USA

Berkshires Home on 11 Acres with Pond an...

Holiday home in Becket near Chester, Massachusetts
Berkshires Home on 11 Acres with Pond and 2 Fire Pits! is located in Becket, 22 km from Cranwell Spa & Golf Club, and provides a patio, garden, and fr...
  • Parking
  • Internet facilities
  • Hairdryer
  • Iron
  • Refrigerator

no reviews

from $383.00 Show details »

Restored 1800s Home Half Mile to Ski Resort! in Otis, USA

Restored 1800s Home Half Mile to Ski Res...

Holiday home in Otis near Chester, Massachusetts
Set 26 km from Cranwell Spa & Golf Club and 30 km from Tanglewood in Otis, Restored 1800s Home Half Mile to Ski Resort! offers accommodation with a ki...
  • Parking

no reviews

from $284.29 Show details »

Berkshires Cabin 2 Mi to Appalachian Trail! in Otis, USA

Berkshires Cabin 2 Mi to Appalachian Tra...

Holiday home in Otis near Chester, Massachusetts
Berkshires Cabin 2 Mi to Appalachian Trail! is located in Otis, 21 km from Cranwell Spa & Golf Club, 25 km from Tanglewood, as well as 26 km from Tang...
  • Parking

no reviews

from $259.00 Show details »

East Otis Reservoir Cabin with Porch - Walk to Lake! in East Otis, USA

East Otis Reservoir Cabin with Porch - W...

Holiday home in East Otis near Chester, Massachusetts
East Otis Reservoir Cabin with Porch - Walk to Lake! is set in East Otis, 35 km from Cranwell Spa & Golf Club, 39 km from Tanglewood, as well as 39 km...
  • Parking
  • Pets allowed

no reviews

from $153.00 Show details »

East Otis Vacation Rental with Private Deck and BBQ! in East Otis, USA

East Otis Vacation Rental with Private D...

Holiday home in East Otis near Chester, Massachusetts
East Otis Romantic Cottage with Deck and BBQ! is situated in East Otis, 35 km from Cranwell Spa & Golf Club, 39 km from Tanglewood, as well as 39 km f...
  • Parking

Fabulous 1 Reviews 9.0

from $206.00 Show details »

Tentrr - Maple Corner Farm Meadow Site in East Otis, USA

Tentrr - Maple Corner Farm Meadow Site

Luxury tent in East Otis near Chester, Massachusetts
Set 39 km from The Big E, 39 km from Eastern States Exposition Center and 42 km from Wintonbury Hills Golf Course, Tentrr - Maple Corner Farm Meadow S...
  • Parking
  • Pets allowed
  • Heating
  • Stovetop
  • Barbecue

no reviews

from $124.00 Show details »

Cabin with 3 Acres, Tennis Courts By 4 Ski Mtns in Sandisfield, USA

Cabin with 3 Acres, Tennis Courts By 4 S...

Holiday home in Sandisfield near Chester, Massachusetts
Situated in Sandisfield, 25 km from Cranwell Spa & Golf Club, 28 km from Norman Rockwell Museum and 29 km from Tanglewood, Cabin with 3 Acres, Tennis ...
  • Parking
  • Pets allowed
  • Internet facilities
  • Hairdryer
  • Refrigerator

Very good 1 Reviews 8.0

from $393.00 Show details »

Tentrr Signature Site - Maple Corner Farm's Berry Patch Site in East Otis, USA

Tentrr Signature Site - Maple Corner Far...

Luxury tent in East Otis near Chester, Massachusetts
Tentrr Signature Site - Maple Corner Farms Berry Patch Site is situated in East Otis, 35 km from The Big E, 36 km from Eastern States Exposition Cente...
  • Parking

no reviews

from $124.00 Show details »

Pet-Friendly Cabin with Fire Pit, BBQ and Great Deck! in Williamsburg, USA

Pet-Friendly Cabin with Fire Pit, BBQ an...

Holiday home in Williamsburg near Chester, Massachusetts
Pet-Friendly Cabin with Fire Pit, BBQ and Great Deck! is situated in Williamsburg, 49 km from Eastern States Exposition Center, 49 km from The Big E, ...
  • Parking
  • Pets allowed

no reviews

from $380.00 Show details »

Picturesque Cottage with Sunroom on Ashmere Lake! in Hinsdale, USA

Picturesque Cottage with Sunroom on Ashm...

Holiday home in Hinsdale near Chester, Massachusetts
Located 32 km from Cranwell Spa & Golf Club, 32 km from Tanglewood Musical Center and 40 km from Norman Rockwell Museum, Picturesque Cottage with Sunr...
  • Parking

Exceptional 1 Reviews 10.0

from $208.00 Show details »

Cozy Monterey Home with Porch Walk to Lake Garfield in Monterey, USA

Cozy Monterey Home with Porch Walk to La...

Holiday home in Monterey near Chester, Massachusetts
Set 22 km from Norman Rockwell Museum, 24 km from Tanglewood and 25 km from Tanglewood Musical Center, Cozy Monterey Home with Porch Walk to Lake Garf...
  • Parking

no reviews

from $304.14 Show details »

Pilgrim Inn in Lee, USA

Pilgrim Inn

Inn in Lee near Chester, Massachusetts , 165 Housatonic Street
Situated in Lee, between the beautiful Beartown and October Mountain State Forests, Pilgrim Inn is a 20-minute drive from Pitsfield.
  • Parking
  • Pets allowed
  • Family rooms
  • Outdoor pool
  • Kids' outdoor play equipment

Pleasant 633 Reviews 6.7

from $89.00 Show details »

Quality Inn in Lee, USA

Quality Inn

Hotel in Lee near Chester, Massachusetts , 170 Housatonic Street
Featuring 2-star accommodation, Quality Inn is located in Lee, 10 km from Tanglewood and 10 km from Tanglewood Musical Center.
  • Parking
  • Family rooms

Very good 480 Reviews 8.2

from $126.65 Show details »

Econo Lodge Lee - Great Barrington in Lee, USA

Econo Lodge Lee - Great Barrington

Motel in Lee near Chester, Massachusetts , 980 Pleasant Street
Located 6 miles from October Mountain State Forest, this Massachusetts hotel features guest rooms with balconies and free Wi-Fi.
  • Parking
  • Telephone
  • Air conditioning
  • Hairdryer
  • Iron

Okay 243 Reviews 5.9

from $85.99 Show details »

Devonfield Inn in Lee, USA

Devonfield Inn

B&B in Lee near Chester, Massachusetts , 85 Stockbridge Rd.
Situated on 30 acres, this scenic Berkshires bed and breakfast boasts a heated, seasonal outdoor pool and on-site tennis courts.
  • Parking
  • Fitness centre
  • Family rooms
  • Swimming pool
  • Swimming Pool

Superb 14 Reviews 9.4

from $392.33 Show details »

The Black Swan Lee - Lenox, Ascend Hotel Collection in Lee, USA

The Black Swan Lee - Lenox, Ascend Hotel...

Hotel in Lee near Chester, Massachusetts , 435 Laurel Street
The Black Swan Lee - Lenox, Ascend Hotel Collection is conveniently located in the foothills of the Berkshire Mountains.
  • Parking
  • Restaurant
  • Pets allowed
  • Bar
  • Fitness centre

Very good 585 Reviews 8.4

from $211.65 Show details »

Holiday Inn Club Vacations Oak n Spruce Resort in the Berkshires an IHG Hotel in South Lee, USA

Holiday Inn Club Vacations Oak n Spruce...

Hotel in South Lee near Chester, Massachusetts , 190 Meadow Street
All rooms feature a flat-screen TV with satellite channels and a private bathroom.
  • Parking
  • Bar
  • Fitness centre
  • Family rooms
  • Indoor pool

Very good 463 Reviews 8.4

from $209.66 Show details »

Elm Motel in Westfield, USA

Elm Motel

Motel in Westfield near Chester, Massachusetts , 50 Russell Road
This motel offers refrigerators in each room and free parking.
  • Parking

Good 202 Reviews 7.4

from $99.00 Show details »

The Ponds at Foxhollow by Capital Vacations in Lenox, USA

The Ponds at Foxhollow by Capital Vacati...

Resort in Lenox near Chester, Massachusetts , 3 Foxhollow Drive
Offering a seasonal outdoor pool and hot tub, The Ponds at Foxhollow is located in Lenox in the Massachusetts Region, 4 km from Tanglewood.
  • Parking
  • Sauna
  • Fitness centre
  • Family rooms
  • Indoor pool

Very good 165 Reviews 8.1

from $399.20 Show details »

Quality Inn Westfield - Springfield in Westfield, USA

Quality Inn Westfield - Springfield

Hotel in Westfield near Chester, Massachusetts , 2 Southampton Road
Offering an complimentary breakfast, Quality Inn Westfield is located in Westfield.
  • Parking
  • Pets allowed

Pleasant 166 Reviews 6.4

from $108.88 Show details »

APPLEJAX cabin steps from a u pick orchard in Sandisfield, USA

APPLEJAX cabin steps from a u pick orcha...

Holiday home in Sandisfield near Chester, Massachusetts , 98 New Hartford Road
Log cabin w/stone fireplace near Ski mountains! in Sandisfield features accommodation with free WiFi, 39 km from Tanglewood, 39 km from Norman Rockwel...
  • Parking
  • Pets allowed
  • Family rooms

Fabulous 1 Reviews 9.0

from $220.50 Show details »

Seven Hills Inn in Lenox, USA

Seven Hills Inn

Inn in Lenox near Chester, Massachusetts , 40 Plunkett St
Located in Lenox, 2.2 km from Cranwell Spa & Golf Club, Seven Hills Inn provides accommodation with free bikes, free private parking, a seasonal outdo...
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Good 300 Reviews 7.2

from $159.00 Show details »

Hampton Inn Westfield in Westfield, USA

Hampton Inn Westfield

Hotel in Westfield near Chester, Massachusetts , 39 Southampton Road
This Westfield, Massachusetts hotel is only moments from Exit 3 on I-90 and near Six Flags New England amusement park.
  • Parking
  • Fitness centre
  • Indoor pool
  • Kid-friendly buffet
  • Swimming pool

Very good 136 Reviews 8.4

from $126.65 Show details »

The Inn at Stockbridge in Stockbridge, USA

The Inn at Stockbridge

B&B in Stockbridge near Chester, Massachusetts , 30 East Street
Set on 12 acres of land less than 2 miles from Berkshire Theatre Festival, this bed and breakfast offers stylish rooms with en suite bathrooms.
  • Pets allowed
  • Fitness centre

Superb 25 Reviews 9.4

from $349.40 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.

Accommodation data and pictures provided by Booking.com