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

Find Extended Stay Hotels in Stockbridge, MA

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
$211 nightly
$236 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 27 - Sep 28
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
$185 nightly
$203 total
Sep 24 - Sep 25
Total with taxes and fees
Shaker Mill Inn

5. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
United States
Robert
$108 nightly
$120 total
Oct 22 - Oct 23
Total with taxes and fees
Berkshire Mountain Lodge

6. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United States
Rosann
$172 nightly
$191 total
Sep 23 - Sep 24
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires

7. East Rock Inn

East Rock Inn
Great Barrington
United States
ERIK
$152 nightly
$170 total
Oct 22 - Oct 23
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 6 - Oct 7
Total with taxes and fees
The Central Downtown Inn & Suites

9. Vacation Village in the Berkshires

Vacation Village in the Berkshires
Williamstown
United States
Jacob
$122 nightly
$136 total
Sep 23 - Sep 24
Total with taxes and fees
Vacation Village in the Berkshires

10. Devonfield Inn B&B

Devonfield Inn B&B
Lee
United States
Sebastien
$439 nightly
$490 total
Sep 23 - Sep 24
Total with taxes and fees
Devonfield Inn B&B
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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

8/10 Good
"I am disappointed that it has been over two weeks and I have yet to receive my room deposit back. They told me 7-10 days"
Graham 2-night trip
Posted 3 hours ago
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"Even in the off season it was beautiful."
Karen 1-night trip
Posted 1 day ago
Jiminy Peak Mountain Resort

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