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

Search Stockbridge Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Stockbridge cottages

House (3 Bedrooms) | Interior

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
$499 nightly
The price is $554
Jul 5 - Jul 6
Total with taxes and fees
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Exterior

Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres
New Lebanon
10.0 out of 10, Exceptional, (1 review)
$2,126 nightly
The price is $2,158
Jul 7 - Jul 8
Total with taxes and fees
Berkshires farm, 30+ guests, 50 acres
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Stockbridge Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Nice place to stay. Will return on our next visit."
Douglas 3-night trip
Posted less than an hour ago
Berkshire Mountain Lodge

Find out more about Stockbridge

Stockbridge Cottages information

Number of reviews
Accommodation
 Cottages
Lowest Price
Highest Price

Frequently asked questions

How much do cottages in Stockbridge cost?
Prepare to pay between and per night for cottages in Stockbridge. Whatever your budget, a terrific stay is only a few clicks away 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.
How many cottages are there in Stockbridge?
Take advantage of your vacation days and choose from cottages in Stockbridge. Yearning for a place where you can immerse yourself in nature? Expedia will help you find the ideal escape in a few easy clicks.
Why book your cottage in Stockbridge with Expedia?
Reserving a cottage in Stockbridge is as simple as working out your travel dates and choosing an ideal place for outdoor recreation and relaxation. From ritzy retreats to affordable stays and cottages that come with conveniences like a kitchen, Expedia has something for all traveler tastes. As for epic deals? We've have them as well!
How can I find cheap cottages in Stockbridge?
With Expedia's helpful filter tool, sourcing cheap cottages in Stockbridge is a snap. To find properties that'll make your wallet happy, narrow down your search by amenities, star rating and budget.
What is there to do in Stockbridge near my cottage?
Stockbridge has enough experiences to keep you entertained for weeks, beginning with National Shrine of the Divine Mercy. Norman Rockwell Museum, Naumkeag Museum and Berkshire Botanical Garden are other popular attractions. If you're staying a while longer, Berkshire Theatre Festival and Mission House will add the finishing touches to your itinerary.

Explore a world of travel with Expedia