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21 Dec - 22 Dec
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Our top choices for West Stockbridge hotels

Garden
Shaker Mill Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (438)
"Nice place, easy check in"
United States
Robert
The price is NZ$218
includes taxes & fees
5 Jan - 6 Jan 2026
Shaker Mill Inn
Exterior
Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1001)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is NZ$99
includes taxes & fees
1 Jan - 2 Jan 2026
Pleasant Valley Motel West Stockbridge
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1005)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is NZ$147
includes taxes & fees
4 Jan - 5 Jan 2026
The Yankee, Trademark Collection by Wyndham
Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites

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, (1000)
"Very friendly and good Breakfast."
United States
Jesse
The price is NZ$148
includes taxes & fees
4 Jan - 5 Jan 2026
Best Western Plus Berkshire Hills Inn & Suites
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (13)
"New hotel very nice"
United States
joel
The price is NZ$262
includes taxes & fees
4 Jan - 5 Jan 2026
Element Lenox Berkshires
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1006)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is NZ$195
includes taxes & fees
11 Jan - 12 Jan 2026
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lobby
Quality Inn Great Barrington

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very good, (1001)
"My go to place for my ski weekends"
United States
Ryan
The price is NZ$147
includes taxes & fees
4 Jan - 5 Jan 2026
Quality Inn Great Barrington
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (710)
"Great hospitality "
United States
regina maria
The price is NZ$208
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very good, (996)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is NZ$180
includes taxes & fees
24 Dec - 25 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Room, 1 Queen Bed, Non Smoking
Monument Mountain Motel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (808)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
Monument Mountain Motel
Terrace/patio
Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (413)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is NZ$210
includes taxes & fees
23 Dec - 24 Dec
Locust Tree Bed and Breakfast LLC
Exterior
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Clean, pleasant staff and good breakfast. "
United States
Edward
The price is NZ$202
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn & Suites Berkshires-Lenox
Outdoor pool, pool loungers
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1001)
"Old time charm and hot tub under the stars"
United States
Lori
The price is NZ$351
includes taxes & fees
14 Jan - 15 Jan 2026
The Red Lion Inn
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (794)
"Spacious room and loved pool and hot tub!"
United States
Deanna
The price is NZ$230
includes taxes & fees
11 Jan - 12 Jan 2026
Berkshire Mountain Lodge
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (659)
"The room was very clean with comfortable King bed. We really enjoyed the hot tub."
United States
Christine
The price is NZ$248
includes taxes & fees
2 Jan - 3 Jan 2026
Hilton Garden Inn Lenox Pittsfield
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (828)
"Staff was very friendly and helpful."
United States
Pamela
The price is NZ$153
includes taxes & fees
23 Dec - 24 Dec
Howard Johnson by Wyndham Lenox
Lobby
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1002)
"The staff is always so helpful & nice, and the rooms are always clean and comfortable. This is my favorite place to stay in Lee!"
United States
Cooper
The price is NZ$160
includes taxes & fees
11 Jan - 12 Jan 2026
Quality Inn Lee - Lenox South
In-room safe, desk, free cots/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (562)
"The staff were very friendly and accommodating "
United States
Tom
The price is NZ$146
includes taxes & fees
23 Dec - 24 Dec
Travelodge by Wyndham Great Barrington Berkshires
Egyptian cotton sheets, premium bedding, down duvets, minibar
Prospect Berkshires

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (15)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
The price is NZ$465
includes taxes & fees
4 Jan - 5 Jan 2026
Prospect Berkshires
Lobby
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
Great Barrington
9.4 out of 10, Exceptional, (758)
"Clean room, very courteous staff "
United States
Thomas
The price is NZ$262
includes taxes & fees
6 Jan - 7 Jan 2026
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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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Stay near popular West Stockbridge attractions

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

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

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
"My stay was great with no problems. "
scott 2-night trip
Posted 2 days ago
Vacation Village in the Berkshires

More cheap accommodation in West Stockbridge

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

461 Pittsfield Rd Lenox MA
The price is NZ$147 per night from 4 Jan to 5 Jan
NZ$147
4 Jan - 5 Jan 2026
includes taxes & fees
9/10 Wonderful! (1,004 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. Provides a children's pool, an indoor pool and free self parking. Holiday Inn & Suites Pittsfield-Berkshires by IHG 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 33 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.

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