A nighttime view of a residential area with houses adorned with holiday lights.

Find Extended Stay Hotels in Stockbridge, MA

  • Upfront pricing

    Our total price for your stay includes taxes and fees
  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key
  • Be picky

    Search almost a million properties worldwide

Top Stockbridge Extended Stay Hotels | Reserve now, pay later

Our top choices for Stockbridge hotels with a kitchen

1. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
James
$209 nightly
$233 total
Sep 30 - Oct 1
Total with taxes and fees
The Red Lion Inn

2. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
United States
Anonymous traveler
$766 nightly
$856 total
Sep 28 - Sep 29
Total with taxes and fees
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

3. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
United States
Linda
$135 nightly
$150 total
Sep 13 - Sep 14
Total with taxes and fees
Holiday Inn Club Vacations Oak 'n Spruce Resort

4. Shaker Mill Inn

Shaker Mill Inn
West Stockbridge
United States
Mervin
$148 nightly
$162 total
Sep 10 - Sep 11
Total with taxes and fees
Shaker Mill Inn

5. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
United States
Robert
$113 nightly
$126 total
Oct 1 - Oct 2
Total with taxes and fees
Berkshire Mountain Lodge

6. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United States
Edward
$172 nightly
$191 total
Sep 10 - Sep 11
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires

7. East Rock Inn

East Rock Inn
Great Barrington
United States
ERIK
$146 nightly
$163 total
Sep 10 - Sep 11
Total with taxes and fees
East Rock Inn

8. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield
United States
Rena
$89 nightly
$100 total
Sep 17 - Sep 18
Total with taxes and fees
The Central Downtown Inn & Suites

9. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
United States
Shelly B.
$148 nightly
$165 total
Sep 16 - Sep 17
Total with taxes and fees
Cozy 1-bedroom studio in serene Great Barrington with AC

10. Devonfield Inn B&B

Devonfield Inn B&B
Lee
United States
Richard
$409 nightly
$457 total
Sep 10 - Sep 11
Total with taxes and fees
Devonfield Inn B&B
View all properties

Find out more about Stockbridge

Discover top Stockbridge attractions

Stockbridge, Massachusetts, offers a delightful mix of culture and nature that will captivate any traveler. Begin your exploration at the Norman Rockwell Museum, where you can admire the works of the beloved American painter and learn about his connections to the town. Next, take a stroll through the scenic Stockbridge Bowl, perfect for a family picnic or a leisurely paddle in the summer months. For a taste of history, visit the historic Naumkeag estate, where you can wander through beautifully designed gardens and opulent interiors that reflect the Gilded Age. Don’t miss the nearby Berkshire Botanical Garden, which showcases stunning plant collections and offers workshops for all ages. Finally, for a bit of adventure, hike the picturesque trails of the Appalachian Trail that wind through the surrounding natural beauty. For accommodations, consider staying in the heart of Stockbridge, where charming inns and boutique hotels provide a cozy atmosphere and personalized service. This area allows easy access to local shops and restaurants, ensuring a seamless blend of leisure and exploration, making it a perfect base for your Berkshire adventure.

Expand your search

Most booked related extended stays in Stockbridge in 2026

Frequently asked questions

Why book an extended stay hotel in Stockbridge through Expedia?
If you're seeking a long-term rental for your extended stay in Stockbridge, Expedia has you covered. Tailor your search results by price, amenities and location to find your ideal long-term stay. Some of these great properties may even offer weekly rates. Want to know how to get the best deals? Sign up to become an Expedia member for free and save loads of cash with exclusive offers — plus you'll receive reward points on every booking. Our extended stay hotels in Stockbridge come with handy amenities like laundries and kitchens, so even though you're miles away, you can still enjoy the feeling of home.
What can I expect from an extended stay hotel?
You'll save money while enjoying convenience and comfort with an extended stay hotel in Stockbridge. Whether you need a studio for yourself or a spacious apartment that'll fit your whole crew, these types of properties have amenities designed to make you feel at home. On top of standard offerings like a gym and a bar, many extended stay hotels have kitchens and a washer and dryer. This means you can make your own tasty meals and wash your own clothes, letting you keep a little jingle in your pocket. Special weekly rates can help you make the most out of your travel budget.

Top Stockbridge Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Always a great stay at. Vacation Villages"
Susan 1-night trip
Posted 8 hours ago
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"My family had a wonderful time at Jiminy Peak Mountain Resort! The staff truly cared about making sure we had a great stay. When we had a last-minute change and needed to upgrade our room, they handled everything so seamlessly and were incredibly accommodating. The space we received was much larger than we expected, with four floors, three bedrooms, two bathrooms, and three pull-out sofas. There was more than enough room for our whole family to stay comfortably, and it was very affordable for the amount of space and amenities we received. They were also very generous with towels and blankets. Although we didn’t end up using everything, it was reassuring to know that plenty was available if we needed more. The view from the backyard was beautiful, and the resort attractions were only minutes away. We especially enjoyed the scenic chairlift ride and mountain coaster. Everyone in our family, from old to young, had a great time. Overall, it was a wonderful and very affordable family getaway. We really appreciated the hospitality, spacious accommodations, beautiful surroundings, and activities for all ages. We would definitely recommend Jiminy Peak Mountain Resort!"
sophia 1-night trip
Posted 1 day ago
Jiminy Peak Mountain Resort

Explore a world of travel with Expedia