A river surrounded by autumn-colored trees and a forested hill.

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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
Stephan
$191 nightly
$214 total
Nov 4 - Nov 5
Total with taxes and fees
The Red Lion Inn

2. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
South Lee
United States
Michael
$135 nightly
$150 total
Oct 20 - Oct 21
Total with taxes and fees
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

3. Shaker Mill Inn

Shaker Mill Inn
West Stockbridge
United States
Steven
$127 nightly
$139 total
Nov 1 - Nov 2
Total with taxes and fees
Shaker Mill Inn

4. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United Kingdom
judith
$160 nightly
$179 total
Oct 27 - Oct 28
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires

5. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
United States
Joel
$113 nightly
$126 total
Nov 16 - Nov 17
Total with taxes and fees
Berkshire Mountain Lodge

6. East Rock Inn

East Rock Inn
Great Barrington
United States
Sharon
$109 nightly
$122 total
Nov 17 - Nov 18
Total with taxes and fees
East Rock Inn

7. Devonfield Inn B&B

Devonfield Inn B&B
Lee
United States
Sebastien
$369 nightly
$412 total
Nov 2 - Nov 3
Total with taxes and fees
Devonfield Inn B&B

8. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield
United States
Debra
$99 nightly
$111 total
Oct 19 - Oct 20
Total with taxes and fees
The Central Downtown Inn & Suites

9. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
United States
Kelly B.
$253 nightly
$282 total
Oct 26 - Oct 27
Total with taxes and fees
Leaf-Peeper Paradise in the Berkshires

10. Vacation Village in the Berkshires

Vacation Village in the Berkshires
Williamstown
United States
Adrianne
$115 nightly
$128 total
Nov 11 - Nov 12
Total with taxes and fees
Vacation Village in the Berkshires
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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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"So good will be back!"
Stephanie 1-night trip
Posted 3 hours ago
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

8/10 Good
"Everything was great here except our keys did not work so I had to go back to front desk for new keys on check in. Then on our 2nd morning we went to breakfast and came back to keys not working again. Front desk was helpful and reprogrammed them right away so not a huge deal. The hotel also has pretty thin walls so noise travels. Luckily our neighbors for the weekend were mostly quiet. I wish we knew John Harvards was closed till Thanksgiving but the other pub was great with an excellent beer selection on tap, great service & live entertainment every night. I wish there was free breakfast but thats not a big deal. I would recommend this place especially if you like to ski. We will consider this location for future Berkshire trips as its a fairly good central county location. Just keep in mind most shopping and restaurants are about 15-20+ minutes away."
Christopher 3-night trip
Posted 2 days ago
Jiminy Peak Mountain Resort

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