Book Cheap Hotels in West Stockbridge

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Most frequently booked West Stockbridge hotels

Shaker Mill Inn

Shaker Mill Inn

2.5 out of 5
2 Oak Street West Stockbridge MA
0.23 km from city centre
The price is CA $144 per night
CA $144
CA $159 total
Dec 10 - Dec 11
includes taxes & fees
Stay at this B&B in West Stockbridge. Enjoy free breakfast, free parking, and daily housekeeping. Popular attractions Ebenezer II Gifts and Antiques and Hotchkiss Mobile Studio are located nearby.
Breakfast included
Parking included
Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

2 out of 5
42 Stockbridge Rd West Stockbridge MA
Free cancellation
Reserve now, pay when you stay
0.98 km from city centre
The price is CA $72 per night
CA $72
CA $80 total
Jan 2 - Jan 3, 2026
includes taxes & fees
Stay at this motel in West Stockbridge. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the clean rooms in our reviews. Popular attractions Hoffman's Pottery and Charles H. Baldwin & Sons are located nearby.
Parking included
Free WiFi
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Free cancellation
Reserve now, pay when you stay
26.48 km from city centre
The price is CA $114 per night
CA $114
CA $142 total
Dec 7 - Dec 8
includes taxes & fees
Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free cancellation
Reserve now, pay when you stay
12.23 km from city centre
Get rates
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Guido's Marketplace and Herman Melville's Arrowhead are located nearby.
Pool
Hot tub
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Free cancellation
Reserve now, pay when you stay
15.72 km from city centre
The price is CA $128 per night
CA $128
CA $143 total
Dec 12 - Dec 13
includes taxes & fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Berkshire Museum and Colonial Theater are located nearby.
Pool
Pet-friendly
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Free cancellation
Reserve now, pay when you stay
9.7 km from city centre
The price is CA $153 per night
CA $153
CA $171 total
Dec 7 - Dec 8
includes taxes & fees
Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Kennedy Park and Pleasant Valley Wilderness Sanctuary are located nearby.
Pet-friendly
Parking included
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Free cancellation
Reserve now, pay when you stay
7.35 km from city centre
The price is CA $180 per night
CA $180
CA $264 total
Jan 4 - Jan 5, 2026
includes taxes & fees
Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Schantz Galleries and Mission House are located nearby.
Pool
Spa
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street South Lee MA
Free cancellation
10.23 km from city centre
The price is CA $149 per night
CA $149
CA $190 total
Dec 8 - Dec 9
includes taxes & fees
Book a stay at this family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in our reviews. Popular attractions Berkshire Theatre Festival and Schantz Galleries are located nearby.
Pool
Air conditioning
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
Free cancellation
Reserve now, pay when you stay
11.3 km from city centre
The price is CA $88 per night
CA $88
CA $98 total
Dec 15 - Dec 16
includes taxes & fees
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Guido's Marketplace and Bousquet Ski Area are located nearby.
Pool
Hot tub
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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.

Top family friendly West Stockbridge hotel deals

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

42 Stockbridge Rd West Stockbridge MA
The price is CA $72 per night from Jan 2 to Jan 3
CA $72
CA $80 total
Jan 2 - Jan 3, 2026
includes taxes & fees
6.6/10 (1,002 reviews)

Top cheap West Stockbridge hotel deals

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

42 Stockbridge Rd West Stockbridge MA
The price is CA $72 per night from Jan 2 to Jan 3
CA $72
CA $80 total
Jan 2 - Jan 3, 2026
includes taxes & fees
6.6/10 (1,002 reviews)

Top hotels in West Stockbridge for Extended Stay

Suite 4 - Quiet and private accommodations in a country setting.

Suite 4 - Quiet and private accommodations in a country setting.

Spencertown NY
10/10 Exceptional! (3 reviews)
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.

West Stockbridge hotels essential information

Accommodation
1,521 hotels
Lowest Price
CA $80
Highest Price
CA $264
Popular hotels
Shaker Mill Inn, Pleasant Valley Motel West Stockbridge, Vacation Village in the Berkshires, Berkshire Mountain Lodge, Holiday Inn & Suites Pittsfield-Berkshires by IHG, Berkshires Untold, The Red Lion Inn, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, The Yankee, Trademark Collection by Wyndham

Frequently asked questions

What are the top kid-friendly hotels in West Stockbridge?
Take some of the hassles out of traveling with little ones by choosing a family-friendly hotel in West Stockbridge. From well-thought-out amenities to extra services, these properties offer perks that'll help make your getaway an effortless one: You're well catered for at Shaker Mill Inn. It comes with complimentary breakfast, pet-friendly facilities and a commitment to making families feel welcome. 3 bdrm Cottage in the heart of the Berkshires. is another great choice. After a big day of sightseeing, come back home to your comfortable room and perks like a swimming pool and a playground.
Where can I find cheap hotels in West Stockbridge?
At Travelocity you'll find really nice hotels in West Stockbridge at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near West Stockbridge rather than in West Stockbridge. We may find you even better rates, too.
How do I find the best West Stockbridge hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in West Stockbridge then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in West Stockbridge?
The cheapest hotel in West Stockbridge is CA $80 This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in West Stockbridge?
There are 1,521 hotels in West Stockbridge on Travelocity.
What are the best hotels in West Stockbridge?
West Stockbridge has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in West Stockbridge for you!
When is the best time to visit West Stockbridge?
If you want the joy of a fun-filled trip in peak season, visit West Stockbridge during March, April and May. If you'd prefer the peace of off-season, book a stay during quieter months, such as August, September and November.
When is the cheapest time to stay in West Stockbridge?
Based on historic data is usually the cheapest month to visit West Stockbridge. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in West Stockbridge?
There are multiple hotels in West Stockbridge that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to West Stockbridge. We have plenty of kid-friendly hotels in West Stockbridge to choose from on Travelocity!
Why book a hotel in West Stockbridge through Travelocity?
Because we have the top hotels in West Stockbridge! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in West Stockbridge on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent West Stockbridge hotel reviews by fellow wanderers

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

5 out of 5
Posted 1 day ago
Travelocity Verified Review
"All of the above "
A verified traveller stayed at The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Hotels near…

Areas of West Stockbridge