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Vacation rentals in Stockbridge

See all Vacation Rentals in Stockbridge
New! Cozy Berkshires Cabin - Walk to Beach & Lake!

New! Cozy Berkshires Cabin - Walk to Beach & Lake!

Stockbridge, MA
This cabin features barbecue grills.
Artist's Cottage on the Lake Mahkeenac

Artist's Cottage on the Lake Mahkeenac

Stockbridge, MA
This cabin includes a garden and barbecue grills.
General Williams Estate House Lenox/stockbridge

General Williams Estate House Lenox/stockbridge

Stockbridge, MA
A garden is available at this vacation home.
"Too Good" With 11 Private Acres. Contact us for Monthly Specials!

"Too Good" With 11 Private Acres. Contact us for Monthly Specials!

Stockbridge, MA
Situated in Stockbridge, this vacation home is within 1 mi (2 km) of Mission House, Berkshire Theatre Festival, and Naumkeag. Beartown State Forest and National Shrine of the Divine Mercy are also within 2 mi (3 km).
Cozy Stockbridge Home - Walk To Golf Course!

Cozy Stockbridge Home - Walk To Golf Course!

Stockbridge, Massachusetts
An outdoor tennis court is featured at this vacation home, along with a garden and barbecue grills.
Modern New England Farmhouse on Prospect Hill

Modern New England Farmhouse on Prospect Hill

Stockbridge, MA
A fitness center is featured at this vacation home, along with a garden.
Completely Renovated Historic Home in the Heart of the Berkshires

Completely Renovated Historic Home in the Heart of the Berkshires

Stockbridge, MA
This vacation home includes a garden and barbecue grills.
A Grand Estate in Historic Stockbridge

A Grand Estate in Historic Stockbridge

Stockbridge, MA
An outdoor tennis court is featured at this vacation home, along with a garden.
One block from Main St Stockbridge

One block from Main St Stockbridge

Stockbridge, MA
Situated in Stockbridge, this vacation home is within a 10-minute walk of Mission House and Berkshire Theatre Festival. Naumkeag and National Shrine of the Divine Mercy are also within 15 minutes.
$96
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 out of 5.0 276 Brodie Mountain Rd, Hancock, MA
4/5
(31 Reviews)
This condo features an outdoor pool and an indoor pool. Enjoy the health club and perks like free self parking and free WiFi. A business center, a terrace, and a garden are also on offer.
$169
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3.0 out of 5.0 37 Corey Rd, Hancock, MA
3.8/5
(13 Reviews)
This smoke-free condo resort features ski-in/ski-out access, 2 outdoor tennis courts, and a restaurant. Take advantage of ski lessons and ski rentals on site, and enjoy downhill skiing and snowboarding. Enjoy the outdoor pool and perks like free self parking and free WiFi.
Jiminy Peak 4 Level Deluxe SKI Condo- 3+ Bedrooms, 2 Baths, Whirlpool,sauna More

Jiminy Peak 4 Level Deluxe SKI Condo- 3+ Bedrooms, 2 Baths, Whirlpool,sauna More

Lanesborough, MA
This condo features an outdoor pool and an indoor pool. Families will appreciate the arcade/game room and barbecue grills. A fitness center, a spa tub, and a sauna are also on offer.
'The Mill River Cabin’ w/ Fireplace & River View!

'The Mill River Cabin’ w/ Fireplace & River View!

Mill River, MA
An outdoor tennis court is featured at this cabin, along with barbecue grills.
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Becket, MA
A garden is available at this cabin.
$300
Private swimming-pool, rap-around porch, and breathtaking views!

Private swimming-pool, rap-around porch, and breathtaking views!

Copake Falls, NY
This cabin includes a garden and barbecue grills.
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The Best Way to Find your Vacation Rentals in Stockbridge

How cheap can a vacation rental in Stockbridge be?

You can find vacation rentals in Stockbridge for as low as $96 per night.

How do you look for the best vacation rental deals in Stockbridge with Travelocity?

Travelocity provides the best vacation rental deals in various locations throughout Stockbridge so you can create the perfect plan for you. You can search and filter by type of property, amenities, neighborhood, price range, number of bedrooms, and more.

Are cancellations free on vacation rentals with Travelocity?

Each vacation rental has its own cancellation policy. It’s essential to understand the terms of your agreement before booking. Most rentals in Stockbridge can be canceled for free when notifying the property before the cancellation deadline.

What types of vacation rentals are available in Stockbridge?

Short term rentals come in all shapes and sizes. Choose from properties for a wide range of budgets and types of holidays. Families, couples, outdoor adventurers, and leisure travelers alike will find the perfect place for them. Check out our Stockbridge vacation apartments to get started building your trip.

What are the benefits of booking a short-term rental in Stockbridge?

Whether it’s for a summer getaway, a winter excursion, or a routine business trip, Stockbridge vacation homes are often an excellent choice. You can enjoy group vacations with short term rentals to fit your party size. You might take a romantic weekend for two or plan a family reunion, and all stay under one roof. The options are endless, and you can find them on Travelocity.

Why is Travelocity the best site to find your vacation rental in Stockbridge?

With Travelocity, all your travel needs are taken care of in one convenient platform. We offer fantastic deals on our large selection of vacation rentals to get you the most savings and rewards back on every booking. Save more when you bundle bookings together, including car rentals, flights, and activities. Here, you can build custom Stockbridge vacations.

How to cancel your vacation rental with Travelocity?

To cancel your vacation rental, contact the property manager. You can find their contact information in the ‘Itinerary’ section of your Travelocity account. Most properties receive a full refund when you cancel before the cancellation deadline. Policies vary by property, so it’s important to understand the terms before booking. For more information, visit our customer service portal.


*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.