Search West Stockbridge hotels

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
15 Feb - 16 Feb
Tomorrow
16 Feb - 17 Feb
Next weekend
20 Feb - 22 Feb
In two weeks
27 Feb - 1 Mar

Filter by

Guest rating
Guest rating
Star rating

Our top choices for West Stockbridge hotels

Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (445 reviews)
  • cleanliness
    Enjoy a relaxing Berkshires retreat with free breakfast and parking amenities.
"Had everything we needed. Very thoughtful touches. "
United States
Mark
The price is NZ$181
includes taxes & fees
2 Mar - 3 Mar
Shaker Mill Inn
Desk, laptop workspace, blackout curtains, iron/ironing board

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,001 reviews)
  • cleanliness
    Cosy Berkshires retreat minutes from Tanglewood with free parking and WiFi.
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is NZ$106
includes taxes & fees
17 Feb - 18 Feb
Pleasant Valley Motel West Stockbridge
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (841 reviews)
  • cleanliness
    Experience the beauty of the Berkshires at a cosy lodge with golf access and pool.
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is NZ$248
includes taxes & fees
16 Feb - 17 Feb
Berkshire Mountain Lodge
Exterior

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (415 reviews)
  • cleanliness
    Experience the charming Locust Tree B&B in East Canaan with free breakfast.
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is NZ$200
includes taxes & fees
16 Feb - 17 Feb
Locust Tree Bed and Breakfast LLC
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (82 reviews)
  • cleanliness
    Relax in the heart of the Berkshires with an indoor pool and spa pool after a day out.
"it was a lovely hotel, hot tub was perfect after the day of skiing, everything very clean and new and lovely breakfast. All staff were very nice."
United States
Laura Pearson
The price is NZ$244
includes taxes & fees
1 Mar - 2 Mar
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Property entrance

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (823 reviews)
  • cleanliness
    Explore city centre Pittsfield from a stylish hotel with complimentary WiFi and parking.
"Great staff, beautiful hotel. Would definitely recommend "
United States
Shawn
The price is NZ$276
includes taxes & fees
19 Feb - 20 Feb
Hotel On North
Breakfast, lunch and dinner served

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (667 reviews)
  • cleanliness
    Perfect setting for a Berkshires visit with an indoor pool and Asian dining.
" Nice staff - beautiful hotel!"
United States
MARY
The price is NZ$254
includes taxes & fees
27 Feb - 28 Feb
Hilton Garden Inn Lenox Pittsfield
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Tranquil Berkshire hideaway near Tanglewood with complimentary amenities.
"Very friendly and good Breakfast."
United States
Jesse
The price is NZ$178
includes taxes & fees
1 Mar - 2 Mar
Best Western Plus Berkshire Hills Inn & Suites
Daily to-go breakfast for a fee

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.2 out of 10, Very good, (989 reviews)
  • cleanliness
    Ski-in/ski-out Jiminy Peak condos with restaurant and pool for alpine enthusiasts.
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is NZ$350
includes taxes & fees
8 Mar - 9 Mar
Jiminy Peak Mountain Resort
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (856 reviews)
  • cleanliness
    Experience Berkshires charm with on-site American dining and attentive service.
"This place was lovely. I travel a lot for my 2 college athletes and I wish I could have spent more time here. Great place! "
United States
Melissa
The price is NZ$223
includes taxes & fees
18 Feb - 19 Feb
Berkshires Untold
Terrace/patio

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (355 reviews)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is NZ$202
includes taxes & fees
1 Mar - 2 Mar
The Central Downtown Inn & Suites
Exterior

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,003 reviews)
  • cleanliness
    Enjoy views of the Berkshires at this comfortable retreat with seasonal outdoor pool.
"Very friendly staff comfy beds!"
United States
Giselle
The price is NZ$171
includes taxes & fees
22 Feb - 23 Feb
The Yankee, Trademark Collection by Wyndham
Lobby lounge

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Convenient Lenox hotel with indoor pool near Tanglewood Music Centre.
"The room and amenities were amazing. "
United States
Kathleen
The price is NZ$220
includes taxes & fees
1 Mar - 2 Mar
Hampton Inn & Suites Berkshires-Lenox
Lobby lounge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (18 reviews)
  • cleanliness
    Relax in the Berkshires with pool access and complimentary breakfast daily.
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is NZ$257
includes taxes & fees
22 Feb - 23 Feb
Element Lenox Berkshires
Exterior

The White Hart

The White Hart
4.0 star property
Salisbury
9.8 out of 10, Exceptional, (146 reviews)
  • cleanliness
    Experience historic charm in this Salisbury hotel with a charming café and lounge.
"Such a cozy, authentic New England hotel, with all its charm. "
United States
Maulik
The price is NZ$518
includes taxes & fees
26 Feb - 27 Feb
The White Hart
Front of property

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (164 reviews)
  • cleanliness
    Charming Berkshires B&B with outdoor pool near Tanglewood Music Centre.
"Everything was perfect - location and accommodation."
United States
Christopher
Brook Farm Inn
Seasonal outdoor pool

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (842 reviews)
  • cleanliness
    Enjoy a tranquil stay near Tanglewood Music Centre with a refreshing pool.
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
The price is NZ$150
includes taxes & fees
22 Feb - 23 Feb
Berkshire Inn
Property amenity

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (601 reviews)
  • cleanliness
    Enjoy the Berkshires with indoor pool and nearby Tanglewood Music Centre.
"Our stay was great! "
United States
Gianna
The price is NZ$233
includes taxes & fees
15 Mar - 16 Mar
Courtyard by Marriott Lenox Berkshires
Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (43 reviews)
  • cleanliness
    Unwind in the Berkshires at this charming B&B with free weekend breakfast.
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
The price is NZ$332
includes taxes & fees
18 Feb - 19 Feb
Wilder House Berkshires
Lobby sitting area

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (101 reviews)
  • cleanliness
    Serene countryside B&B near Queechy Lake offers free breakfast and parking.
"Great property, very comfortable, incredible staff, easy access to skiing in the area!"
United States
Dominick
The price is NZ$258
includes taxes & fees
3 Mar - 4 Mar
Inn at Silver Maple Farm
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.
View all properties

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Stay near popular West Stockbridge attractions

Charles H. Baldwin & Sons

This historic shop has crafted pure vanilla extract using traditional methods since 1888. Visit the charming shopfront to discover artisanal extracts and baking ingredients.
See properties

Hotchkiss Mobile Studio

Witness the artistry of balance at Hotchkiss Mobiles, where handcrafted contemporary designs come to life in an open studio. Browse unique American crafts while watching mobile-making first-hand.
See properties

Learn more about West Stockbridge

The historic Turn Park Art Space showcases outdoor sculptures along winding paths overlooking the Housatonic River. Grab breakfast at Six Depot Roastery before browsing the charming shops and galleries along Main Street.

See all hotels in West Stockbridge
Olivias Overlook - West Stockbridge, Massachusetts

Top West Stockbridge Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Fairly clean and staff were friendly"
Michael 2-night trip
Posted 2 days ago
Vacation Village in the Berkshires

More cheap accommodation in West Stockbridge

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA
The price is NZ$128 per night from 16 Feb to 17 Feb
NZ$128
16 Feb - 17 Feb
includes taxes & fees
7.4/10 Good! (830 reviews)

Frequently asked questions

What's the best place to stay in West Stockbridge?
Shaker Mill Inn is ranked highly by Expedia customers. This B&B offers free breakfast and free parking. Another favourite option for your trip based on reviews is Pleasant Valley Motel West Stockbridge. See all available top hotels, or vacation rentals in West Stockbridge.
What are some of the best holiday rentals that West Stockbridge has to offer?
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This highly rated holiday home rental in West Stockbridge is located near skiing, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games. See all vacation rentals in West Stockbridge.
If I need to cancel my hotel reservation in West Stockbridge, will I receive a refund?
Yes! You'll find that most hotel reservations are fully refundable if cancelled prior to the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If you have a reservation that's non-refundable, you might still have the option to cancel and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in West Stockbridge.
What is the top LGBTQ-friendly hotel in West Stockbridge?
Shaker Mill Inn is a top LGBTQ-friendly B&B that features free breakfast and free parking. See all available hotels listed as LGBTQ-friendly in West Stockbridge.
What are some hotels with pools in West Stockbridge?
Vacation Village in the Berkshires: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool and free self parking. Berkshire Mountain Lodge and The Yankee, Trademark Collection by Wyndham are a couple of other choices with an on-site pool. View all hotels with pools in West Stockbridge.
What is staying in West Stockbridge like?
Budget-minded travellers will find good deals in West Stockbridge, and many visitors will definitely appreciate the gardens and restaurants. Tourists can also enjoy so much more including its lake views. In West Stockbridge, there are 34 hotels and other accommodation options to choose from. Find out more about West Stockbridge.
What should I do while I'm visiting West Stockbridge?
Attractions such as Charles H. Baldwin & Sons, Hotchkiss Mobile Studio and Ebenezer II Gifts and Antiques are fun for children of all ages. A couple of additional sights to add to your itinerary are Stockbridge Bowl and Hoffman's Pottery. Take a look at what more there is to see and do in Expedia's West Stockbridge guide.
What's the weather like in West Stockbridge?
The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in West Stockbridge are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

Explore a world of travel with Expedia