Book Hotels in Stockbridge, MA

Start date: Check-in selected.
To Date
End date: Check-out

Cabins, apartments, houseboats! We offer comfortable & private vacation rentals

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Filter by

Guest rating
Guest rating
Star rating
Payment type
Payment type
Property type
Property type
Neighborhood
Neighborhood
Traveler experience
Traveler experience
Popular locations
Popular locations
Meal plans available
Meal plans available
Amenities
Amenities
Accessibility
Accessibility

Top Stockbridge hotels

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 out of 5
26 Glendale Road, RR 183, Stockbridge, MA
$414 nightly
The price is $462 total per night from Nov 27 to Nov 28
$462 total
Nov 27 - Nov 28
Total with taxes and fees
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this bed & breakfast. Guests will appreciate free perks like continental breakfast ...
It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!

Reviewed on Oct 27, 2025

Opens in a new windowThe Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $126 total per night from Nov 30 to Dec 1
$126 total
Nov 30 - Dec 1
Total with taxes and fees
This lodge features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, ...
Everything was so perfect for a weekend to just get away and decompress, the staff were great, the room was awesome.

Reviewed on Nov 4, 2025

Opens in a new windowBerkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $104 total per night from Nov 17 to Nov 18
$104 total
Nov 17 - Nov 18
Total with taxes and fees
A restaurant and a bar/lounge are featured at this lodge. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a lobby ...
Enjoyed the Clubhouse before retiring in for the evening. Cozy, comfortable, and relaxing atmosphere.

Reviewed on Nov 10, 2025

Opens in a new windowBerkshires Untold
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3 out of 5
435 Laurel St, Lee, MA
Fully refundable
$110 nightly
The price is $122 total per night from Dec 2 to Dec 3
$122 total
Dec 2 - Dec 3
Total with taxes and fees
A restaurant and a 24-hour gym are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self ...
The view of the lake was great and we loked the location. The restaurant downstairs was great. The bed was hard and we didn't sleep well and the shower was horrible, the worst draining shower I've had in my life. Rooms are dated and decks could use repair.

Reviewed on Nov 7, 2025

Opens in a new windowThe Black Swan Lee - Lenox, an Ascend Collection Hotel
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
$183 nightly
The price is $205 total per night from Nov 16 to Nov 17
$205 total
Nov 16 - Nov 17
Total with taxes and fees
This smoke-free hotel includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi ...
I love the ambience - historic and comfortable and excellent food.

Reviewed on Nov 5, 2025

Opens in a new windowThe Red Lion Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $133 total per night from Nov 14 to Nov 15
$133 total
Nov 14 - Nov 15
Total with taxes and fees
This condo features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks ...
We loved almost everything, but they need to replace sofa, armchair and the bed in this unit. Too old. The sofa and armchair have bad smell of very old furniture.

Reviewed on Nov 7, 2025

Opens in a new windowVacation Village in the Berkshires
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $94 total per night from Nov 25 to Nov 26
$94 total
Nov 25 - Nov 26
Total with taxes and fees
A gym, free self parking, and free newspapers are featured at this hotel. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. ...
The staff was amazing, so kind and accommodating. The room was clean, the beds were very comfortable. Nice breakfast options. We were in town for a concert at Mahaiwe and we didn’t use our car once we checked in… a great home base for the weekend. Will definitely be back.

Reviewed on Nov 6, 2025

Opens in a new windowQuality Inn
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $99 total per night from Nov 15 to Nov 16
$99 total
Nov 15 - Nov 16
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public ...
Great stay! Nice quiet room for 2 little “alert “ to outside noise pups!! Comfy beds and central location for the day trips we had planned.

Reviewed on Nov 8, 2025

Opens in a new windowHoliday Inn & Suites Pittsfield-Berkshires by IHG
Tanglewood Suites

Tanglewood Suites

2.5 out of 5
MA-102, Stockbridge, MA
$219 nightly
The price is $219 total per night from Dec 1 to Dec 2
$219 total
Dec 1 - Dec 2
Total with taxes and fees
A steam room, free self parking, and barbecue grills are featured at this bed & breakfast. Enjoy the free continental breakfast each morning. A garden and a ...
Bed was quite comfortable and the setting was in a beautiful neighborhood. Excellent proximity to Tanglewood. And host gave exceptional information regarding local eateries and things to do. I would have liked to have known at booking that the owner does not accept credit (as the hotels.com app allows ...

Reviewed on Aug 11, 2025

Opens in a new windowTanglewood Suites
Don't see what you're looking for?
See all available properties in Stockbridge
View all properties
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.

Stockbridge Hotel & Travel Guide

Stockbridge offers visitors a broad selection of ideal hotel and apartment possibilities to select from. Travelocity's booking page currently is where modern travelers can compare 37 establishments within a 6-mile (10-kilometer) distance of Stockbridge's urban core.

Scouring the internet for a place to lay your head close to the bright lights of inner-city Stockbridge has been made so easy. Our easy to use booking page features the The Cottage B&B and The Red Lion Inn, which await your arrival within a radius of 0.6-mile (1-kilometer) of the urban center.

The Rookwood Inn can be found about 5 miles (8 kilometers) from central Stockbridge. Another place to stay is the Gateways Inn & Restaurant, which is located about 5 miles (8 kilometers) away. Some other hotels include the Hampton Terrace Inn and the Cranwell Spa and Golf Resort.

Once you and your traveling partner have got to know Stockbridge, why not tour a little bit more of the region? The Western Massachusetts region has countless things to offer visitors. Get to know Western Massachusetts's history museums and fall in love with the area's mountains. In this fascinating part of United States of America visitors may also partake in skiing, cross-country skiing and mountain biking.

Lanesborough is 18 miles (29 kilometers) north of Stockbridge and features Mount Greylock State Reservation Visitor Center and Skyline Country Club. The The Weathervane Motel and Lanesborough Country Inn are a few of the Travelocity long and short-stay alternatives in Lanesborough. 25 miles (42 kilometers) north of Stockbridge, you'll reach Williamstown, which is home to the The Spring's Inn and Berkshire Hills Country Inn. If you visit Williamstown, make sure you visit the Williams College and Williams College Museum of Art.

If you think of sport as your life and enjoy watching local matches you and your family could visit Times Union Center, found 35 miles (54 kilometers) to the northwest of Stockbridge. Wise visitors that need to find accommodation options close by can read about the Hilton Albany or the TownePlace Suites by Marriott Albany Downtown/Medical Center.

Albany International Airport is a major entry point for those flying into and leaving Stockbridge. You can find it 40 miles (65 kilometers) from the town center. For travelers who would like to stay close by, check out Albany Marriott or Homewood Suites by Hilton Albany.

Frequently asked questions

What are the top kid-friendly hotels in Stockbridge?
Family getaways are where the best memories are made, but traveling with little ones can be a challenge. These kid-friendly Stockbridge hotels come with perks designed to keep travelers of all ages relaxed and happy: Tanglewood Suites will help make your next trip the best one yet. It comes with a range of nice little touches, such as complimentary breakfast and an outdoor entertainment area. Also consider A Grand property in Historic Stockbridge. It comes with animal viewing activities, a king bed and lots of opportunities to spend time together.
Where can I find cheap hotels in Stockbridge?
At Travelocity you'll find really nice hotels in 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 Stockbridge rather than in Stockbridge. We may find you even better rates, too.
How do I find the best Stockbridge hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in 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 Stockbridge?
The cheapest hotel in Stockbridge is $94. 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 Stockbridge?
There are 1,353 hotels in Stockbridge on Travelocity.
What are the best hotels in Stockbridge?
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 Stockbridge for you!
When is the best time to visit Stockbridge?
If you want the joy of a fun-filled trip in peak season, visit Stockbridge during February, March and April. If you'd prefer the peace of off-season, book a stay during quieter months, such as November, December and January.
When is the cheapest time to stay in Stockbridge?
Based on historic data is usually the cheapest month to visit 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 Stockbridge?
There are multiple hotels in 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 Stockbridge. We have plenty of kid-friendly hotels in Stockbridge to choose from on Travelocity!
Why book a hotel in Stockbridge through Travelocity?
Because we have the top hotels in 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 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 Stockbridge hotel reviews by fellow wanderers

Berkshires Untold

Berkshires Untold

5 out of 5
Posted 2 days ago
Travelocity Verified Review
"Enjoyed the Clubhouse before retiring in for the evening. Cozy, comfortable, and relaxing atmosphere."
A verified traveler stayed at Berkshires Untold
Berkshires Untold

Explore More Ways to Travel with Travelocity