Stockbridge, MA Vacation Rentals

Our Favorite Vacation Rentals in Stockbridge

  • Villa with Access to 2 Pools, a Hot Tub, an 18-Hole Mini Golf Course, and More
     Villa
    RedAwning
    From
    $146
  • Cozy Stockbridge Home - Walk To Golf Course!
     2br Home/Apartment
    HolidayLettings
    From
    $401
  • Spacious Villa with Access to Pools, a Hot Tub, Mini Golf, and a Sauna!
     2br Villa
    RedAwning
    From
    $220
  • Cozy Berkshire Home, 1 Mile to Stockbridge Center!
     4br Home/Apartment
    HolidayLettings
    From
    $387
  • Villa with Access to Pools, a Hot Tub, Mini Golf, and a Sauna! Great Location!
     2br Villa
    RedAwning
    From
    $195
  • Tranquil 3BR Stockbridge House w/Private Deck
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $452
  • Berkshire Farmhouse Vacation
    Excellent5br Farmhouse
    HolidayLettings
    From
    $342
  • Comfortable Farmhouse in the Berkshires
    Excellent5br Farmhouse
    HolidayLettings
    From
    $471

Check prices for these upcoming dates

Stockbridge Vacation Rentals with a Pool

  • Stockbridge: 4 bed/ 4 bath with heated pool
    Good4br Home/Apartment
    Airbnb
    From
    $550
  • The Guesthouse at Summerhouse Stockbridge. + pool
    Excellent2br Home/Apartment
    Airbnb
    From
    $291
  • Magical Country Retreat in the Berkshires
    Excellent10br Home/Apartment
    Airbnb
    From
    $4,068
  • Luxury Modern House in Berkshires with Pool
     3br Home/Apartment
    Airbnb
    From
    $542

Stockbridge Vacation Rentals with Wi-Fi

  • Stockbridge Carriage House
    Good3br Home/Apartment
    Airbnb
    From
    $452
  • Hideaway in the Woods
    Excellent3br Home/Apartment
    Airbnb
    From
    $509
  • Charming secluded Stockbridge home near Tanglewood
    Excellent5br Home/Apartment
    Airbnb
    From
    $735
  • Cozy cottage by the brook
    ExcellentHome/Apartment
    Airbnb
    From
    $198

Stockbridge Pet-Friendly Vacation Rentals

  • Garfield House
     2br Home/Apartment
    HolidayLettings
    From
    $265
  • 3BR Lee House w/ Easy Access to Main Street!
     3br Home/Apartment
    HolidayLettings
    From
    $411
  • Walk To Tanglewood, Stocbridge Bowl, Wheatleigh, HTD Pool, Hot Tub, Luxury Home
     5br Home/Apartment
    HolidayLettings
    From
    $1,781
  • Lakefront Berkshires Ski/Summer House, Great Views
    Nice4br Home/Apartment
    HolidayLettings
    From
    $330

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
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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
60° -5°
3
67°
1
74° 19°
5
83° 36°
4
85° 39°
5
90° 51°
4
86° 43°
2
85° 34°
3
73° 29°
8
66° 11°
4
53°
5
54° -11°
5
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Rainy days

This climate histogram shows you the weather patterns in Stockbridge. The hottest month in Stockbridge is June, when temperatures peak at 90 ˚F. The coolest month is December, when temperatures drop to -11 ˚F. The wettest month in Stockbridge is March with 8.3 inches of rain, while the driest month is October with 1.25 inches of rain.

What Expert Travelers Think

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Vacation Rentals in Stockbridge

Browse accommodations from all the leading providers including Airbnb, Priceline, Agoda and many more at AllTheRooms.com. We have 242 vacation rentals, hotels and other places to stay in Stockbridge ranging from budget options to luxury places to stay. For those trying to keep costs down, the lowest priced place to stay in Stockbridge comes in at $65 a night. The average price of an accommodation is around $673 per night.

If you need an internet connection during your time in Stockbridge, then you can choose from over 82 places to stay that have WiFi internet. 8 of our accommodations include a breakfast in the price. Fitness fanatics can get a workout in during their stay by choosing from 5 accommodations that have gym facilities. Driving to Stockbridge? Then choose one of the 76 places to stay that comes with a parking spot included. We track 11 places to stay that have a pool or jacuzzi.

AllTheRooms has 28 pet-friendly places to stay in Stockbridge, so if you're traveling with your cat or dog you won't have any trouble.

142 of the accommodations in Stockbridge have been rated by previous guests. They rated 76% as great. 65 places to stay in are instantly bookable.

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