West Stockbridge Vacation Rentals

Our Favorite Vacation Rentals in West Stockbridge

  • Villa with Access to 2 Pools, a Hot Tub, an 18-Hole Mini Golf Course, and More
     Villa
    RedAwning
    From
    $146
  • Comfortable Farmhouse in the Berkshires
    Excellent5br Farmhouse
    HolidayLettings
    From
    $471
  • Spacious Villa with Access to Pools, a Hot Tub, Mini Golf, and a Sauna!
     2br Villa
    RedAwning
    From
    $220
  • Tranquil 3BR Stockbridge House w/Private Deck
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $452
  • Villa with Access to Pools, a Hot Tub, Mini Golf, and a Sauna! Great Location!
     2br Villa
    RedAwning
    From
    $195
  • Gartner House, a charming home in Lenox
    Excellent4br Home/Apartment
    HolidayLettings
    From
    $307
  • Cozy Stockbridge Home - Walk To Golf Course!
     2br Home/Apartment
    HolidayLettings
    From
    $401
  • Lakefront Berkshires Ski/Summer House, Great Views
    Nice4br Home/Apartment
    HolidayLettings
    From
    $333

Check prices for these upcoming dates

West Stockbridge Vacation Rentals with a Pool

  • Luxury Modern House in Berkshires with Pool
     3br Home/Apartment
    Airbnb
    From
    $542
  • Stockbridge: 4 bed/ 4 bath with heated pool
    Good4br Home/Apartment
    Airbnb
    From
    $564
  • Berkshire Valley Retreat
     5br Home/Apartment
    Airbnb
    From
    $1,113
  • Berkshire Winter and Ski Mountain Retreat
    Excellent4br Home/Apartment
    Airbnb
    From
    $986

West Stockbridge Vacation Rentals with Wi-Fi

  • The Sweet Spot
    Excellent3br Home/Apartment
    Airbnb
    From
    $157
  • 1850's Berkshire farmhouse
    Excellent5br Farmhouse
    Airbnb
    From
    $333
  • To Ski or Not to Ski... July weeks Available.
    Good4br Home/Apartment
    Airbnb
    From
    $424
  • Cozy Stockbridge Cottage
    Excellent2br Cottage
    Airbnb
    From
    $136

West Stockbridge Pet-Friendly Vacation Rentals

  • Garfield House
     2br Home/Apartment
    HolidayLettings
    From
    $265
  • Hillhouse Log Cabin
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $487
  • Romantic Berkshire Cottage on Storybook Estate
    ExcellentCottage
    HolidayLettings
    From
    $321
  • NEW! Lakefront Berkshires House w/Deck, Dock +Boat
     4br Home/Apartment
    HolidayLettings
    From
    $388

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 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 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 Weather in West Stockbridge

Rainy days
54° -11°
5
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
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Rainy days

This climate histogram shows you the weather patterns in West Stockbridge. The hottest month in West Stockbridge is June, when temperatures peak at 90 ˚F. The coolest month is December, when temperatures drop to -11 ˚F. The wettest month in West 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

  • — 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
  • — Like the buttons on the calendar which say today, tomorrow - that will make it easy for booking on the road. Website looks great - clean and easy to understand.

    Samantha Wragg
    Samantha WraggCoco Travels
  • — As a mom of 5 kids who enjoy traveling, I love AllTheRooms! It is quick and easy to find the best deal on lodging that fits our family, in the area we'd like. AllTheRooms really does save you time, money, and hassle.

    Becky
    BeckyKid World Citizen

Destinations near West Stockbridge

  • Boston3,425 Properties
  • Nantucket3,127 Properties
  • Provincetown2,177 Properties
  • Eastham1,497 Properties
  • Dennis Port1,411 Properties
  • Chatham1,369 Properties
  • Brewster1,268 Properties
  • Wellfleet1,198 Properties
  • Orleans1,133 Properties
  • Oak Bluffs1,088 Properties
  • Somerville991 Properties
  • Edgartown957 Properties
  • West Yarmouth886 Properties
  • Cambridge859 Properties
  • Falmouth837 Properties
  • Mashpee812 Properties
  • Hyannis782 Properties
  • Brookline733 Properties
  • South Yarmouth723 Properties
  • Tisbury686 Properties
  • Plymouth645 Properties
  • Rockport644 Properties
  • East Falmouth628 Properties
  • North Truro572 Properties
  • Gloucester562 Properties
  • South Chatham550 Properties
  • Lenox526 Properties
  • West Dennis518 Properties
  • Harwich479 Properties
  • Worcester474 Properties
  • Salem455 Properties
  • Dennis441 Properties
  • East Sandwich426 Properties
  • Centerville424 Properties
  • Harwich Port415 Properties
  • Hancock411 Properties
  • Great Barrington394 Properties
  • Revere381 Properties
  • Vineyard Haven380 Properties
  • Waltham373 Properties
  • Lee353 Properties
  • Northampton350 Properties
  • Sandwich334 Properties
  • Quincy327 Properties
  • Truro324 Properties
  • Newton319 Properties
  • Watertown313 Properties
  • Williamstown308 Properties
  • Medford306 Properties
  • Newburyport299 Properties
  • Marblehead292 Properties
  • Pittsfield292 Properties
  • South Dennis256 Properties
  • North Falmouth253 Properties
  • Chelsea253 Properties
  • Amherst251 Properties
  • Marshfield236 Properties
  • Stockbridge234 Properties
  • Arlington226 Properties
  • Osterville220 Properties
  • Barnstable216 Properties
  • Wareham199 Properties
  • Scituate195 Properties
  • Woburn180 Properties
  • West Harwich178 Properties
  • Chilmark163 Properties
  • Bourne156 Properties
  • Sturbridge149 Properties
  • Fairhaven132 Properties
  • Winthrop126 Properties
  • Ipswich112 Properties
  • Westport112 Properties
  • Marlborough105 Properties
  • Hull95 Properties
  • New Marlborough82 Properties
  • Sheffield76 Properties
  • Manchester74 Properties
  • Springfield64 Properties
  • Concord63 Properties
  • Sudbury47 Properties
  • Ashburnham33 Properties
  • Cheshire21 Properties
  • Hubbardston7 Properties