Stockbridge, MA Vacation Rentals

Our Favorite Vacation Rentals in Stockbridge

Quaint, cozy cabin in the woods

Booking.comFrom $425
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Fabulous NEW Spacious House in the Berkshires Tanglewood

HolidayLettingsFrom $372
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Heart Of The Berkshires

Booking.comFrom $155
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Family-friendly Cottage Near Lake, Tanglewood
Excellent
HolidayLettingsFrom $398
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Cozy & Modern Home -mins from Tanglewood & Kripalu
Excellent
HolidayLettingsFrom $172
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Tanglewood / Berkshires - 2 Bed 2 Bath Apartment

HolidayLettingsFrom $429
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Comfortable Farmhouse in the Berkshires
Excellent
HolidayLettingsFrom $429
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Heart of the Berkshires!
Good
HolidayLettingsFrom $271
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Stockbridge Vacation Rentals with a Pool

Stockbridge: 4 Bed/4 bath with Heated Pool!
Good
AirbnbFrom $756
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The Guesthouse at Summerhouse Stockbridge. + pool
Excellent
AirbnbFrom $330
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Berkshires Rustic Retreat (but near everything!)
Excellent
AirbnbFrom $157
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Artists' Family Home
Excellent
AirbnbFrom $336
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Stockbridge Vacation Rentals with Wi-Fi

Stockbridge Carriage House
Good
AirbnbFrom $523
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Historic Stockbridge Home - The Berkshires
Excellent
AirbnbFrom $385
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Hideaway in the Woods
Excellent
AirbnbFrom $432
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Charming secluded Stockbridge home near Tanglewood

AirbnbFrom $729
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Stockbridge Pet-Friendly Vacation Rentals

To Ski or Not to Ski? Great conditions Great fireplace.Your Choice.
Excellent
HolidayLettingsFrom $458
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Just the Spot! Cozy home by the Lake...

HolidayLettingsFrom $220
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NEW! Monterey Home w/Porch by Beach & State Parks!

HolidayLettingsFrom $412
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|The Escape |STOCKBRIDGE| NEW Home |BERKSHIRES|

HolidayLettingsFrom $630
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Stockbridge, Massachusetts Travel Guide

Stockbridge, Massachusetts is a town in the western part of the state that has ample history, historical monuments and stunning nature.

Things to Do in Stockbridge, Massachusetts

The famous American author Norman Rockwell was from Stockbridge, Massachusetts, giving the town a worthy claim to fame. His former home has been converted into a living museum that contains artwork and memorabilia to celebrate his life. Naumkeag is another interesting historic site located here and is a 19th-century vacation home that can now be toured. The home has retained its original furnishings and character.

The Berkshire Botanical Garden is a pleasant place to enjoy an afternoon stroll and take in the fragrant scent of the various colorful plants and flowers growing here.

Best Time to Visit Stockbridge, Massachusetts

Stockbridge, Massachusetts is best visited in the summer months.

Price and Availability in Stockbridge

Most expensive

Most availability

The most expensive month to stay in a vacation rental in Stockbridge is in September, while the cheapest month is in April. The most popular time to book a vacation rental in Stockbridge is in the high season in August. Stockbridge has its low season in April, when less people are visiting and the vacation home occupancy rate drops.

The cheapest day to stay at a vacation rental in Stockbridge tends to be Wednesday, while the most expensive day tends to be Friday. Vacation homes in Stockbridge tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.

The Weather in Stockbridge

SEE FULL WEATHER FORECAST:

86º 40º

2.56

91º 42º

3.42

93º 46º

4.68

90º 51º

8.25

89º 40º

6.89

79º 27º

2.84

64º 0º

6.39

59º 9º

3.94

61º -10º

4.66

73º -3º

4.09

55º 7º

2.35

67º 18º

3.63

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Jan

Feb

Mar

Apr

Rainy days

SEE FULL WEATHER FORECAST:

This climate histogram shows you the weather patterns in Stockbridge. The hottest month in Stockbridge is June, when temperatures peak at 93 ˚F. The coolest month is January, when temperatures drop to -10 ˚F. The wettest month in Stockbridge is August with 8.25 inches of rain, while the driest month is March with 2.35 inches of rain.

What Expert Travelers Think

— When I plan a trip, I no longer waste time visiting multiple websites in search of the best accommodations. Now, I just go to AllTheRooms and immediately find everything from luxury villas to pet-friendly rentals! All in one place
Whitney WearTravel Better Guide
Travel Better Guide
— Whenever I am making travel plans I always use comparison sites to find the best accommodation for us at the best price. Whether it be for hotel stays or private rentals AllTheRooms makes this so much easier and quicker as it brings all my searches into one place, with a great offering of options
Sarah PoolTammymum
Visit Tammymum
— I love AllTheRooms because it is not only local homes for renting, and not only hotels, but everything combined. When I am about to book a place to stay, I usually spend a couple of hours looking through both hotel sites and local home sites, comparing the prices and places.
Alli SimsAlli Sims
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Vacation Rentals in Stockbridge

At AllTheRooms.com we have accommodations from all of the best providers - Airbnb, VRBO, Homeaway and more. Stockbridge has 239 hotels, vacation rentals and other unique places to stay, with prices to suit budget travelers, luxury travelers and everything in between. When traveling on a budget, the cheapest place to stay in Stockbridge is available at $66 per night. The average price of a rental is $581 per night.

If you would like to stay connected during your trip, then you can choose from over 117 accommodations in Stockbridge that have WiFi. We have 9 accommodations that include a breakfast included. Fitness fanatics can get a workout in during their stay by choosing from 10 accommodations that have gyms. Driving to Stockbridge? Then choose one of the 108 places to stay that comes with a parking spot included. 11 places to stay have a a pool or jacuzzi

Those traveling with a cat, dog or some other animal can stay in any of 37 accommodations that are designated as pet-friendly.

In Stockbridge AllTheRooms currently aggregates hotels, vacation rentals, hostels from more than 7 providers, including 73 places to stay from Airbnb, 14 accommodations from VRBO and 14 places to stay from Homeaway.

143 accommodations in Stockbridge have been reviewed; 74% are rated excellent or good. 44 places to stay in are instantly bookable.