Destination Photo

West Stockbridge Vacation Rentals

  1. Vacation Rental Search
  2. United States of America
  3. Massachusetts
  4. West Stockbridge

Our Favorite Vacation Rentals in West Stockbridge

  • Gartner House, a charming home in Lenox
    Gartner House, a charming home in Lenox
    Excellent4br Home/Apartment
    HolidayLettingsFrom $307
    View Deal
  • Berkshires Spacious Comfortable Charming Farmhouse
    Berkshires Spacious Comfortable Charming Farmhouse
    Nice3br Farmhouse
    HolidayLettingsFrom $448
    View Deal
  • Tanglewood / Berkshires - 2 Bed 2 Bath Apartment
    Tanglewood / Berkshires - 2 Bed 2 Bath Apartment
     2br Home/Apartment
    HolidayLettingsFrom $576
    View Deal
  • RiverSong Suite In The Berkshires
    RiverSong Suite In The Berkshires
    Excellent1br Home/Apartment
    HolidayLettingsFrom $256
    View Deal
  • Berkshire Getaway ~ Romantic Tower Suite on Storybook Estate
    Berkshire Getaway ~ Romantic Tower Suite on Storybook Estate
     1br Home/Apartment
    HolidayLettingsFrom $303
    View Deal
  • Renovated 2 bedroom in Heart of Lenox
    Renovated 2 bedroom in Heart of Lenox
     2br Home/Apartment
    HolidayLettingsFrom $464
    View Deal
  • Charming and Spacious Colonial Farmhouse on 4 Acre Estate
    Charming and Spacious Colonial Farmhouse on 4 Acre Estate
     4br Farmhouse
    HolidayLettingsFrom $635
    View Deal
  • West Stockbridge Retreat with private backyard
    West Stockbridge Retreat with private backyard
    Excellent4br Home/Apartment
    AirbnbFrom $311
    View Deal
See all 111 deals in West Stockbridge

West Stockbridge Vacation Rentals with a Pool

  • Idyllic Berkshires Retreat With Pond Views & Pool
    Idyllic Berkshires Retreat With Pond Views & Pool
    Excellent2br Home/Apartment
    AirbnbFrom $466
    View Deal
  • Berkshires Rustic Retreat (close to everything!)
    Berkshires Rustic Retreat (close to everything!)
    Excellent1br Home/Apartment
    AirbnbFrom $170
    View Deal
  • The East Street Cabin
    The East Street Cabin
    ExcellentHome/Apartment
    AirbnbFrom $229
    View Deal
  • The Oliver Wendell Holmes Guesthouse @ Holmesdale
    The Oliver Wendell Holmes Guesthouse @ Holmesdale
     1br Home/Apartment
    AirbnbFrom $331
    View Deal
See all deals in West Stockbridge with a pool

West Stockbridge Vacation Rentals with Wi-Fi

  • Stockbridge Bowl home
    Stockbridge Bowl home
    Good3br Home/Apartment
    AirbnbFrom $283
    View Deal
  • Fiddlehead Farm Private Estate
    Fiddlehead Farm Private Estate
    Excellent4br Home/Apartment
    AirbnbFrom $763
    View Deal
  • Elegant country French stone house in Stockbridge
    Elegant country French stone house in Stockbridge
     3br Home/Apartment
    AirbnbFrom $1695
    View Deal
  • Forest Cabin
    Forest Cabin
    Excellent1br Cabin
    AirbnbFrom $264
    View Deal
See all deals in West Stockbridge with WiFis

West Stockbridge Pet-Friendly Vacation Rentals

  • Berkshires, Lenox, MA. Close to Tanglewood
    Berkshires, Lenox, MA. Close to Tanglewood
    Excellent3br Home/Apartment
    AirbnbFrom $819
    View Deal
  • Tentrr - The Lodge's Signature Site
    Tentrr - The Lodge's Signature Site
     1br Home/Apartment
    AirbnbFrom $130
    View Deal
  • Tentrr - Berkshire Mountain Hideaway
    Tentrr - Berkshire Mountain Hideaway
     1br Home/Apartment
    AirbnbFrom $125
    View Deal
  • Monumental Industrial Castle
    Monumental Industrial Castle
     10br Home/Apartment
    AirbnbFrom $2430
    View Deal
See all deals in West Stockbridge that allow pets

West Stockbridge Travel Guide

West Stockbridge is a small town in Berkshire County, Massachusetts. With a population of under 2,000 people, life runs at a slow, relaxing pace.

Things to Do in West Stockbridge

West Stockbridge is home to ponds, streams and wetlands, and the beautiful Williams River which flows through the center of town. You can also visit the nearby Berkshire Botanical Garden to see a pretty collection of plants and flowers, plus go for walks in the surrounding rambling, hilly countryside.

Best Time to Visit West Stockbridge

Visit in the summer months of June, July and August, when the weather is sunny and you can enjoy a stroll beside the Williams River.

Price and Availability in West Stockbridge

Most expensive
Most availability
, , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0
Powered by:
The most expensive month to stay in a vacation rental in West Stockbridge is in July, while the cheapest month is in April. The most popular time to book a vacation rental in West Stockbridge is in the high season in August. West 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 West Stockbridge tends to be Tuesday, while the most expensive day tends to be Friday. Vacation homes in West Stockbridge tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.

The Weather in West Stockbridge

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
86º 40º
2.56
91º 42º
3.42
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Rainy days
This climate histogram shows you the weather patterns in West Stockbridge. The warmest months in West Stockbridge are June and July, when temperatures reach 93 ˚F. The coolest month is January, when temperatures drop to -10 ˚F. The wettest month in West 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

Vacation Rentals in West Stockbridge

Pick the perfect rental for your trip at AllTheRooms.com. We aggregate Airbnb, Priceline, Bed and Breakfast and more. We have 111 vacation rentals, hotels and other accommodation types in West Stockbridge ranging from low-cost options to extravagant places to stay. For those traveling on a budget, the cheapest place to stay in West Stockbridge is available at $33.76 per night. On average, an accommodation in West Stockbridge will cost you $660 per night.

If you would like to stay connected during your vacation, then you can choose from over 71 accommodations in West Stockbridge that have WiFi. 3 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 gyms. Driving to West Stockbridge? Then choose one of the 66 places to stay that comes with a parking spot included.

If you're traveling with a furry friend, then be sure to select one of the 21 pet-friendly accommodations available.

80 of our rentals in West Stockbridge have been reviewed by previous guests. They rated 75% as excellent or good. 24 places to stay in are instantly bookable.

Destinations near West Stockbridge