Find Extended Stay Hotels in Stockbridge, MA

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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
Merideth
$228 nightly
$254 total
Aug 23 - Aug 24
Total with taxes and fees
The Red Lion Inn

2. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
United States
Kimberly
$143 nightly
$159 total
Sep 7 - Sep 8
Total with taxes and fees
Holiday Inn Club Vacations Oak 'n Spruce Resort

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
United States
Joseph
$138 nightly
$155 total
Aug 30 - Aug 31
Total with taxes and fees
Berkshire Mountain Lodge

4. Shaker Mill Inn

Shaker Mill Inn
West Stockbridge
United States
Mervin
$206 nightly
$226 total
Aug 10 - Aug 11
Total with taxes and fees
Shaker Mill Inn

5. East Rock Inn

East Rock Inn
Great Barrington
United States
ERIK
$149 nightly
$167 total
Aug 23 - Aug 24
Total with taxes and fees
East Rock Inn

6. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United States
Edward
$206 nightly
$231 total
Aug 25 - Aug 26
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires

7. Devonfield Inn B&B

Devonfield Inn B&B
Lee
United States
Francis
$389 nightly
$435 total
Sep 3 - Sep 4
Total with taxes and fees
Devonfield Inn B&B

8. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield
United States
Rena
$91 nightly
$102 total
Sep 3 - Sep 4
Total with taxes and fees
The Central Downtown Inn & Suites

9. Vacation Village in the Berkshires

Vacation Village in the Berkshires
Williamstown
United States
Brooks
$106 nightly
$118 total
Sep 7 - Sep 8
Total with taxes and fees
Vacation Village in the Berkshires

10. Becket Motel

Becket Motel
Becket
United States
Paul
$123 nightly
$138 total
Aug 30 - Aug 31
Total with taxes and fees
Becket Motel
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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.

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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

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

8/10 Good
"Jiminy Peak is located in an absolutely beatiful location in the Berkshires. And it has fun family-friendly summertime activities. But it could use some sprucing up. The pool liner is a little wrinkly and the hot tub is quite stained near the water line. In addition, our room had a nice 2-foot gouge in the wall seemingly caused by the corner of the armchair beneath it. It seems that could/should have been repaired before out arrival. And the dated counertops and fixtures are showing their age. That said, so am I! On the plus side: the iconic scenery, the friendly helpful staff, and the amenities. All in all, a good value for a family getaway. I would definitely recommend the prolerty overall."
Fausto 2-night trip
Posted 11 hours ago
Jiminy Peak Mountain Resort

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