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

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
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,000 reviews)
"Great location - hotel has an excellent dining room and there are several other restaurants within easy walking distance from hotel. A historic, old hotel with lots of curated artwork and history."
United States
Lisabeth
$197 nightly
The price is $220
Nov 29 - Nov 30
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
10.0 out of 10, Exceptional, (42 reviews)
"The house was lovely - my sisters and I had a wonderful time. Everything was warm and welcoming - it felt like home! We hope to make it an annual visit :)"
United States
Anonymous traveler
$738 nightly
The price is $824
Dec 7 - Dec 8
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 in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
3.5 star property
South Lee
9.2 out of 10, Wonderful, (1,000 reviews)
"Nice place to stay"
United States
Michael
$128 nightly
The price is $143
Nov 15 - Nov 16
Total with taxes and fees
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

4. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (483 reviews)
"Loved the location, fireplace and vibe"
United States
Mahadeva
$145 nightly
The price is $159
Nov 15 - Nov 16
Total with taxes and fees
Shaker Mill Inn

5. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,269 reviews)
"Excellent stay!!!!"
United States
Susan J
$106 nightly
The price is $118
Dec 14 - Dec 15
Total with taxes and fees
Berkshire Mountain Lodge

6. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.4 out of 10, Exceptional, (1,000 reviews)
"Lovely room, comfortable bed and a nice breakfast."
United Kingdom
judith
$178 nightly
The price is $198
Nov 15 - Nov 16
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires

7. East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (58 reviews)
"East Rock was a nice, clean, and comfortable place to stay. Everything was great, and I enjoyed my stay."
United States
Sharon
$117 nightly
The price is $131
Dec 13 - Dec 14
Total with taxes and fees
East Rock Inn

8. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (141 reviews)
"Wonderful location and hosts are amazing. Breakfast was great. Clean."
United States
Sebastien
$369 nightly
The price is $412
Nov 16 - Nov 17
Total with taxes and fees
Devonfield Inn B&B

9. Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
9.8 out of 10, Exceptional, (28 reviews)
"excellent lakeside view"
United States
mike
$116 nightly
The price is $129
Nov 18 - Nov 19
Total with taxes and fees
Berkshire Lake Lodge

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

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
8.8 out of 10, Excellent, (10 reviews)
"great location , berkshires are awesome . very clean , host is excellent ."
United States
bob i.
$104 nightly
The price is $116
Nov 20 - Nov 21
Total with taxes and fees
Cozy 1-bedroom studio in serene Great Barrington with AC
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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.

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