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
$196 nightly
$219 total
Nov 2 - Nov 3
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
Jared
$129 nightly
$144 total
Oct 6 - Oct 7
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
Mervin
$138 nightly
$151 total
Nov 3 - Nov 4
Total with taxes and fees
Shaker Mill Inn

4. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United States
Rosann
$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
Jay
$111 nightly
$124 total
Nov 2 - Nov 3
Total with taxes and fees
Berkshire Mountain Lodge

6. 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

7. East Rock Inn

East Rock Inn
Great Barrington
United States
ERIK
$120 nightly
$134 total
Nov 2 - Nov 3
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
Oct 15 - Oct 16
Total with taxes and fees
The Central Downtown Inn & Suites

9. Vacation Village in the Berkshires

Vacation Village in the Berkshires
Williamstown
United States
Denton
$110 nightly
$123 total
Nov 1 - Nov 2
Total with taxes and fees
Vacation Village in the Berkshires

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

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
United States
Deborah S.
$125 nightly
$140 total
Oct 11 - Oct 12
Total with taxes and fees
Cozy 1-bedroom studio in serene Great Barrington with AC
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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
"Great location and great amenities!!"
Phillip 1-night trip
Posted 2 hours ago
Vacation Village in the Berkshires

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