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Accommodations in Chester (Page 6)

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)
Charming Adams Home Near Dtwn, Trails and More! in Adams, USA

Charming Adams Home Near Dtwn, Trails an...

Holiday home in Adams near Chester, Massachusetts
Charming Adams Home Near Dtwn, Trails and More! is situated in Adams, 37 km from Cranwell Spa & Golf Club, 37 km from Tanglewood Musical Center, and 4...
  • Parking

no reviews

from $101.00 Show details »

The Trail in Adams - Berkshires' Art Hotel in Adams, USA

The Trail in Adams - Berkshires' Art Hot...

B&B in Adams near Chester, Massachusetts , 10 Pleasant Street
Located in the heart of the Berkshires, this eco-friendly bed and breakfast offers on-site massage services.
  • Parking
  • Sauna
  • Family rooms
  • Allergy-free room
  • Electric vehicle charging station

Very good 24 Reviews 8.4

from $218.75 Show details »

Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4 in Hancock, USA

Unique Yeti-Theme Ski On Off Suite Jimin...

Holiday home in Hancock near Chester, Massachusetts , 37 Corey Road
Within 33 km of Tanglewood and 33 km of Cranwell Spa & Golf Club, Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4 features free WiFi and a fitness ...
  • Parking
  • Fitness centre
  • Indoor pool
  • Outdoor pool
  • Swimming pool

Superb 16 Reviews 9.2

from $162.77 Show details »

Ski On Off 1BR Suite 1st Flr Sleeps 4 Jiminy Peak in Hancock, USA

Ski On Off 1BR Suite 1st Flr Sleeps 4 Ji...

Holiday home in Hancock near Chester, Massachusetts , 37 Corey Road
Located about 33 km from Tanglewood, Ski On Off 1BR Suite 1st Flr Sleeps 4 Jiminy Peak offers accommodation with an outdoor pool and free WiFi.
  • Parking
  • Fitness centre
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Fabulous 4 Reviews 8.8

from $156.75 Show details »

Deluxe Ski On Off 1BR Suite Sleeps 4 on Jiminy Mtn in Hancock, USA

Deluxe Ski On Off 1BR Suite Sleeps 4 on...

Holiday home in Hancock near Chester, Massachusetts , 37 Corey Road
Within 33 km of Tanglewood and 33 km of Cranwell Spa & Golf Club, Deluxe Ski On Off 1BR Suite Sleeps 4 on Jiminy Mtn features free WiFi and a fitness ...
  • Parking
  • Fitness centre

Superb 12 Reviews 9.0

from $183.08 Show details »

Mountain View Suite Sleeps 4 Ski OnOff Jiminy Peak in Hancock, USA

Mountain View Suite Sleeps 4 Ski OnOff J...

Holiday home in Hancock near Chester, Massachusetts , Corey Road 37
Situated about 33 km from Tanglewood, Mountain View Suite Sleeps 4 Ski OnOff Jiminy Peak offers accommodation with an outdoor pool and free WiFi.
  • Parking
  • Fitness centre
  • Indoor pool
  • Outdoor pool
  • Swimming pool

Exceptional 6 Reviews 10.0

from $171.33 Show details »

Gorgeous 1st FL Mtn View Jiminy Suite Sleeps 4 Ski On Off in Hancock, USA

Gorgeous 1st FL Mtn View Jiminy Suite Sl...

Apartment in Hancock near Chester, Massachusetts , Corey Road 37
Set about 33 km from Tanglewood, Gorgeous 1st FL Mtn View Jiminy Suite Sleeps 4 Ski On Off offers accommodation with an outdoor pool and free WiFi.
  • Parking
  • Indoor pool
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $198.67 Show details »

Disney Magic at Jiminy Mountain in Hancock, USA

Disney Magic at Jiminy Mountain

Hotel in Hancock near Chester, Massachusetts , 37 Corey Road 712
Located 33 km from Tanglewood, Disney Magic at Jiminy Mountain offers 4-star accommodation in Hancock and has a shared lounge, a restaurant and a bar.
  • Parking
  • Restaurant
  • Bar
  • Sauna
  • Fitness centre

Fabulous 19 Reviews 8.8

from $206.69 Show details »

Gorgeous New Zen Suite Sleeps 4-Ski On Off Jiminy in Hancock, USA

Gorgeous New Zen Suite Sleeps 4-Ski On O...

Holiday home in Hancock near Chester, Massachusetts , Corey Road 37
Within 33 km of Tanglewood and 33 km of Cranwell Spa & Golf Club, Gorgeous New Zen Suite Sleeps 4-Ski On Off Jiminy provides free WiFi and a fitness c...
  • Parking
  • Fitness centre
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Superb 6 Reviews 9.0

from $162.77 Show details »

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk in Hancock, USA

WOW-New Ski OnOff Suite By Pool Sleeps 4...

Holiday home in Hancock near Chester, Massachusetts , Corey Road 37
Within 33 km of Tanglewood and 33 km of Cranwell Spa & Golf Club, WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk features free WiFi and a fitness ...
  • Parking
  • Fitness centre
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Superb 11 Reviews 9.1

from $171.33 Show details »

Jurassic Dino Suite Jiminy-Must See Sleeps 4 in Hancock, USA

Jurassic Dino Suite Jiminy-Must See Slee...

Apartment in Hancock near Chester, Massachusetts , Corey Road 37
Within 33 km of Tanglewood and 33 km of Cranwell Spa & Golf Club, Jurassic Dino Suite Jiminy-Must See Sleeps 4 features free WiFi and a fitness centre...
  • Fitness centre
  • Indoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $197.67 Show details »

Fair vacation rentals 3 in Springfield, USA

Fair vacation rentals 3

Apartment in Springfield near Chester, Massachusetts , 149 Dickinson Street
Fair vacation rentals 3, a property with a terrace, is set in Springfield, 5.8 km from The Big E, 39 km from Wintonbury Hills Golf Course, as well as ...
  • Parking
  • Family rooms

no reviews

from $224.10 Show details »

Club Wyndham Bentley Brook in Hancock, USA

Club Wyndham Bentley Brook

Hotel in Hancock near Chester, Massachusetts , 1 Corey Road
Located in Hancock just 35 miles from Norman Rockwell Museum, this hotel features an indoor and outdoor pool.
  • Parking
  • Sauna
  • Fitness centre
  • Family rooms
  • Outdoor pool

Fabulous 331 Reviews 8.7

from $159.64 Show details »

Gorgeous Ski On/Off 2 BR Sleeps 8 Jiminy-Must See Luxury in Hancock, USA

Gorgeous Ski On/Off 2 BR Sleeps 8 Jiminy...

Aparthotel in Hancock near Chester, Massachusetts , 8 Corey Road
Located in Hancock in the Massachusetts region, Gorgeous Ski On/Off 2 BR Sleeps 8 Jiminy-Must See Luxury provides accommodation with free WiFi and fre...
  • Parking
  • Sauna
  • Indoor pool
  • Swimming pool
  • Swimming Pool

Fabulous 15 Reviews 9.0

from $346.20 Show details »

Jiminy Peak Mountain Resort in Hancock, USA

Jiminy Peak Mountain Resort

Resort in Hancock near Chester, Massachusetts , 37 Corey Road
Nestled on Hancock, Massachusetts’ ski slopes, Jiminy Peak Mountain Resort offers a restaurant, adventure parks and ski-to-door access.
  • Parking
  • Restaurant
  • Bar
  • Sauna
  • Fitness centre

Good 232 Reviews 7.7

from $169.00 Show details »

Vacation Village in the Berkshires in Hancock, USA

Vacation Village in the Berkshires

Holiday park in Hancock near Chester, Massachusetts , 276 Brodie Mountain Road
Nestled in the scenic hills and countryside of the Berkshires in Hancock, Massachusetts, this hotel offers recreational activities.
  • Parking
  • Fitness centre
  • Family rooms
  • Indoor pool
  • Outdoor pool

Very good 1332 Reviews 8.5

from $144.12 Show details »

The Springs Motel in New Ashford, USA

The Springs Motel

Hotel in New Ashford near Chester, Massachusetts , 94 U.S. 7
Located in New Ashford, 30 km from Tanglewood, The Springs Motel provides accommodation with free WiFi and free private parking.
  • Parking
  • Swimming pool
  • Swimming Pool

Very good 65 Reviews 8.2

from $183.33 Show details »

Honey Spot in Springfield, USA

Honey Spot

Apartment in Springfield near Chester, Massachusetts , 97 Newfield Road
Situated 10 km from Eastern States Exposition Center, 10 km from The Big E and 33 km from Amherst College, Honey Spot features accommodation located i...
  • Parking
  • Family rooms
  • Indoor pool
  • Swimming pool

Exceptional 35 Reviews 9.8

from $150.00 Show details »

Newly Renovated 2 Floor Apartment Getaway in Springfield, USA

Newly Renovated 2 Floor Apartment Getawa...

Apartment in Springfield near Chester, Massachusetts , 200 Commonwealth Avenue
Newly Renovated 2 Floor Apartment Getaway is located in Springfield, 6.9 km from Eastern States Exposition Center, 7.1 km from The Big E, and 39 km fr...
  • Parking
  • Family rooms

Good 8 Reviews 7.5

from $320.00 Show details »

Fearlessrose vacation Rental in Springfield, USA

Fearlessrose vacation Rental

Guest house in Springfield near Chester, Massachusetts , 89 Appleton Street
Located in Springfield, 7.3 km from Eastern States Exposition Center, Fearlessrose vacation Rental provides accommodation with free WiFi and free priv...
  • Parking
  • Family rooms
  • Kids' outdoor play equipment
  • Tea/Coffee maker
  • Shower

Superb 19 Reviews 9.2

from $273.00 Show details »

Fair vacation rental in Springfield, USA

Fair vacation rental

Apartment in Springfield near Chester, Massachusetts , 895 Belmont Avenue
Located in Springfield in the Massachusetts region, Fair vacation rental features a balcony.
  • Parking
  • Family rooms

Poor 14 Reviews 3.9

from $107.28 Show details »

Hancock Log Cabin Retreat 2 Miles to Jiminy Peak! in Hancock, USA

Hancock Log Cabin Retreat 2 Miles to Jim...

Holiday home in Hancock near Chester, Massachusetts
Situated in Hancock, 34 km from Tanglewood and 34 km from Cranwell Spa & Golf Club, Hancock Log Cabin Retreat 2 Miles to Jiminy Peak! provides accommo...
  • Parking
  • Shower
  • Bath
  • TV
  • Hairdryer

Exceptional 1 Reviews 10.0

from $226.00 Show details »

Howard Johnson by Wyndham Springfield in Springfield, USA

Howard Johnson by Wyndham Springfield

Hotel in Springfield near Chester, Massachusetts , 1356 Boston Road
Featuring free WiFi, Howard Johnson Express - Springfield offers accommodation in Springfield.
  • Parking
  • Family rooms

Passable 301 Reviews 5.5

from $83.30 Show details »

Cavalier Cottage B&B in Shelburne Falls, USA

Cavalier Cottage B&B

B&B in Shelburne Falls near Chester, Massachusetts , 236 East Oxbow Road
Cavalier Cottage B&B boasts an on-site garden and is 28 km from Adams.
  • Parking
  • Pets allowed
  • Breakfast in the room
  • Shower
  • Air conditioning

Fabulous 10 Reviews 8.9

from $180.00 Show details »

Inn at Silver Maple Farm in East Chatham, USA

Inn at Silver Maple Farm

B&B in East Chatham near Chester, Massachusetts , 1871 State Route 295
Situated in East Chatham, 22 km from Stockbridge, Inn at Silver Maple Farm features air-conditioned rooms and free private parking.
  • Parking
  • Allergy-free room

Superb 56 Reviews 9.4

from $229.00 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.

Accommodation data and pictures provided by Booking.com