Stockbridge, MA Vacation Rentals

Our Favorite Vacation Rentals in Stockbridge

  • Tentrr - Living Water Campsites: Ski N' Zip 1
     Country House
    Booking.com
    From
    $120
  • Cozy Stockbridge Home - Walk To Golf Course!
     2br Home/Apartment
    HolidayLettings
    From
    $414
  • Heart Of The Berkshires
     Home/Apartment
    Booking.com
    From
    $155
  • Tranquil 3BR Stockbridge House w/Private Deck
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $426
  • Tentrr - Living Water Campsites: Ski N' Zip 2
     Country House
    Booking.com
    From
    $120
  • Spacious Villa with Access to Pools, a Hot Tub, Mini Golf, and a Sauna!
     2br Villa
    HolidayLettings
    From
    $242
  • Berkshire Farmhouse Vacation
    Excellent5br Farmhouse
    HolidayLettings
    From
    $386
  • Cozy Modern Condo for the Berkshires
     2br Home/Apartment
    HolidayLettings
    From
    $377

Check prices for these upcoming dates

Stockbridge Vacation Rentals with a Pool

  • General Williams House
    Excellent6br Home/Apartment
    Airbnb
    From
    $1,074
  • The Guesthouse at Summerhouse Stockbridge. + pool
    Excellent2br Home/Apartment
    Airbnb
    From
    $257
  • Holiday Inn Club/ Oak and Spruce, Berkshires
     2br Home/Apartment
    Airbnb
    From
    $226
  • Best of the Berkshires in a perfect family size!
     4br Home/Apartment
    Airbnb
    From
    $351

Stockbridge Vacation Rentals with Wi-Fi

  • Stockbridge Carriage House
    Good3br Home/Apartment
    Airbnb
    From
    $452
  • Historic Stockbridge Home - The Berkshires
    Excellent4br Home/Apartment
    Airbnb
    From
    $396
  • Hideaway in the Woods
    Excellent3br Home/Apartment
    Airbnb
    From
    $509
  • Charming secluded Stockbridge home near Tanglewood
    Excellent5br Home/Apartment
    Airbnb
    From
    $735

Stockbridge Pet-Friendly Vacation Rentals

  • Heart of the Berkshires!
    Good3br Home/Apartment
    HolidayLettings
    From
    $288
  • Garfield House
     2br Home/Apartment
    HolidayLettings
    From
    $265
  • Lakefront Berkshires Ski/Summer House, Great Views
    Nice4br Home/Apartment
    HolidayLettings
    From
    $323
  • Romantic Berkshire Cottage on Storybook Estate
    ExcellentCottage
    HolidayLettings
    From
    $321

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
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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 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 Weather in Stockbridge

Rainy days
64°
6
59°
4
61° -10°
5
73° -3°
4
55°
2
67° 18°
4
86° 40°
3
91° 42°
3
93° 46°
5
90° 51°
8
89° 40°
7
79° 27°
3
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Rainy days

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 December, when temperatures drop to -10 ˚F. The wettest month in Stockbridge is May with 8.25 inches of rain, while the driest month is October with 2.35 inches of rain.

What Expert Travelers Think

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    Laurelle McVicker
    Laurelle McVickerLaurelle McVicker
  • — 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 Pool
    Sarah PoolTammymum
  • — When I first opened up the AllTheRooms.com site, I was impressed right away... When I’m traveling, I don’t like to waste time searching multiple engines for accommodations, it gets overwhelming and frustrating fast. I want a unique, comfortable stay for the best deal

    Kaelin
    KaelinKindly Kae

Vacation Rentals in Stockbridge

Choose the perfect rental for your trip at AllTheRooms.com. We aggregate Airbnb, Bed and Breakfast, Priceline and others. Stockbridge has 272 hotels, vacation rentals and other unique places to stay, with prices to suit budget travelers, luxury travelers and everything in between. For those wanting to save money, the lowest priced place to stay in Stockbridge comes in at $75 a night. On average, an accommodation in Stockbridge will cost you $620 per night.

If you need to stay connected during your trip, then you can choose from over 92 accommodations in Stockbridge that have WiFi. We have 10 accommodations that include a breakfast included. Fitness fanatics can get a workout in during their stay by choosing from 7 accommodations that have gym facilities. Driving to Stockbridge? Then choose one of the 82 places to stay that comes with a parking spot included. We have 11 accommodations that have a pool or jacuzzi.

Those traveling with a cat, dog or some other animal can stay in one of 30 accommodations that are designated as pet-friendly.

157 of the accommodations in Stockbridge have been reviewed and rated. 74% are rated excellent or good. 63 accommodations allow instant booking.

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