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Search and Rent Stockbridge Condos

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Our top choices for Stockbridge condo rentals

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Vacation Village in the Berkshires

Condo in Williamstown

Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2184)
"Awesome for ski"
United States
Lazar
$126 nightly
The price is $141
Jan 4 - Jan 5, 2026
Total with taxes and fees
Vacation Village in the Berkshires
Pool
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

Condo in Hancock

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
8.0 out of 10, Very Good, (8)
"Perfect spot for Mountain Adventures, property was well equipped with comfortable necessities. It was very clean and spacious for six people, 3 adults and 3 young boys. We would definitely stay again. "
United States
PK N.
$301 nightly
The price is $336
Jan 5 - Jan 6, 2026
Total with taxes and fees
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Interior
UNIQUE - 1BR Country Condo @ Jiminy Peak

Condo in Hancock

UNIQUE - 1BR Country Condo @ Jiminy Peak
10.0 out of 10, Exceptional, (14)
"Clean, comfortable place with nice amenities. "
United States
Mike H.
$348 nightly
The price is $389
Jan 8 - Jan 9, 2026
Total with taxes and fees
UNIQUE - 1BR Country Condo @ Jiminy Peak
Pool
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

Condo in Hancock

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
9.0 out of 10, Wonderful, (2)
"very nice and roomy! really enjoyed."
United States
Shack M.
$270 nightly
The price is $302
Jan 6 - Jan 7, 2026
Total with taxes and fees
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
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.
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Top Stockbridge Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"The bed was very comfortable. The staff was helpful and courteous"
Timothy 1-night trip
Posted 2 days ago
The Yankee, Trademark Collection by Wyndham

Find out more about Stockbridge

Stockbridge Condo Rentals information

Number of reviews
2,203
Accommodation
43 Condo Rentals
Lowest Price
$141
Highest Price
$389

Frequently asked questions

How much do condos in Stockbridge cost?
Expect to pay from $141 to $389 per night for condos in Stockbridge. No matter your budget, you'll find the perfect stay on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your condo in Stockbridge with Expedia?
Use Expedia to find your dream condo in Stockbridge. After a luxury escape? Try out our filters to search for properties with a 5-star rating. If you have a fixed budget, click on how much you want to spend and then browse our amazing options. We'll help you find the perfect fit whatever your vacation looks like.
How can I find cheap condos in Stockbridge?
Expedia can help you locate cheap condos in Stockbridge. To find your dream stay in a couple of clicks, simply use our handy filter tool to tailor your search results by star rating, budget and amenities.
What is there to do in Stockbridge near my condo?
Stockbridge has enough sights and experiences to keep you occupied for weeks (or months!), starting with National Shrine of the Divine Mercy. Norman Rockwell Museum, Naumkeag Museum and Berkshire Botanical Garden are other well-known attractions. If you're in town a while, Berkshire Theatre Festival and Mission House are worthwhile additions to your itinerary.

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