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
    $171
  • The Escape at Stockbridge
     Country House
    Booking.com
    From
    $588
  • Cozy Stockbridge Home - Walk To Golf Course!
     2br Home/Apartment
    HolidayLettings
    From
    $414
  • Spacious Villa with Access to Pools, a Hot Tub, Mini Golf, and a Sauna!
     2br Villa
    RedAwning
    From
    $195
  • Tentrr - Running Spring Farm
     Country House
    Booking.com
    From
    $115
  • Cozy Berkshire Home, 1 Mile to Stockbridge Center!
     4br Home/Apartment
    HolidayLettings
    From
    $414
  • Villa with Access to Pools, a Hot Tub, Mini Golf, and a Sauna! Great Location!
     2br Villa
    RedAwning
    From
    $176
  • Heart Of The Berkshires
    ExcellentHome/Apartment
    Booking.com
    From
    $155

Check prices for these upcoming dates

Stockbridge Vacation Rentals with a Pool

  • General Williams House
    Excellent6br Home/Apartment
    Airbnb
    From
    $1,074
  • Berkshires Rustic Retreat (close to everything!)
    ExcellentHome/Apartment
    Airbnb
    From
    $158
  • Best of the Berkshires in a perfect family size!
     4br Home/Apartment
    Airbnb
    From
    $351
  • Charming Berkshires Cottage
    ExcellentHome/Apartment
    Airbnb
    From
    $249

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

  • Tranquil 3BR Stockbridge House w/Private Deck
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $438
  • Fabulous NEW Spacious House in the Berkshires Tanglewood
     4br Home/Apartment
    HolidayLettings
    From
    $408
  • Berkshire Farmhouse Vacation
    Excellent5br Farmhouse
    HolidayLettings
    From
    $342
  • Heart of the Berkshires!
    Good3br Home/Apartment
    HolidayLettings
    From
    $288

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
, , , , , , , , , , , 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 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
89 º40
7
79 º27
3
64 º0
6
59 º9
4
61 º-10
5
73 º-3
4
55 º7
2
67 º18
4
86 º40
3
91 º42
3
93 º46
5
90 º51
8
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
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

  • — 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 Wear
    Whitney WearTravel Better Guide
  • — 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
  • — 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 Sims
    Alli SimsAlli Sims

Vacation Rentals in Stockbridge

At AllTheRooms.com we have accommodations from all of the best providers - Airbnb, Bed and Breakfast, Priceline and others. AllTheRooms has 255 vacation rentals, hotels and other great places to stay while you enjoy Stockbridge, with everything from budget hostels and homestays to extravagant Airbnbs and hotels. When traveling on a budget, the most economical place to stay in Stockbridge is available at $75 per night. An average rental in Stockbridge costs on average $627 a night.

Those looking to get some work finished during their trip to Stockbridge can pick from 125 places to stay that have WiFi. We have 10 accommodations that include a breakfast included. You can maintain your workout regime by staying at one of 10 accommodations that provide gym facilities. If you are driving to Stockbridge, you'll want to pick from 116 places to stay that provide parking. We have 11 hotels and vacation rentals that have a pool or jacuzzi.

AllTheRooms has 39 pet-friendly places to stay in Stockbridge, so if you're traveling with your pet you won't have any problems.

158 of the accommodations in Stockbridge have been reviewed and rated. 73% are rated great. You can instantly book any of 58 places to stay right now.

Destinations near Stockbridge

  • Boston4,334 Properties
  • Nantucket3,133 Properties
  • Provincetown2,336 Properties
  • Eastham1,535 Properties
  • Dennis Port1,501 Properties
  • Brewster1,413 Properties
  • Chatham1,340 Properties
  • Wellfleet1,273 Properties
  • Orleans1,221 Properties
  • Oak Bluffs1,153 Properties
  • Somerville1,114 Properties
  • Edgartown998 Properties
  • Cambridge997 Properties
  • West Yarmouth963 Properties
  • Falmouth927 Properties
  • Hyannis892 Properties
  • Mashpee885 Properties
  • Brookline847 Properties
  • Rockport781 Properties
  • Tisbury758 Properties
  • South Yarmouth752 Properties
  • East Falmouth679 Properties
  • Plymouth675 Properties
  • Gloucester649 Properties
  • South Chatham592 Properties
  • North Truro574 Properties
  • Dennis538 Properties
  • Lenox536 Properties
  • West Dennis522 Properties
  • Harwich518 Properties
  • Worcester505 Properties
  • Centerville496 Properties
  • East Sandwich467 Properties
  • Salem463 Properties
  • Harwich Port444 Properties
  • Waltham438 Properties
  • Great Barrington437 Properties
  • Hancock411 Properties
  • Lee407 Properties
  • Northampton394 Properties
  • Newton387 Properties
  • Vineyard Haven384 Properties
  • Revere354 Properties
  • Sandwich350 Properties
  • Williamstown345 Properties
  • Newburyport342 Properties
  • Quincy341 Properties
  • Medford341 Properties
  • Truro340 Properties
  • North Falmouth338 Properties
  • Watertown322 Properties
  • Pittsfield309 Properties
  • Marblehead307 Properties
  • Amherst265 Properties
  • Chelsea264 Properties
  • Marshfield258 Properties
  • South Dennis255 Properties
  • Arlington245 Properties
  • Osterville232 Properties
  • Barnstable231 Properties
  • Woburn224 Properties
  • Scituate212 Properties
  • West Harwich203 Properties
  • Wareham202 Properties
  • Sturbridge190 Properties
  • Bourne180 Properties
  • Chilmark174 Properties
  • Marlborough152 Properties
  • Fairhaven132 Properties
  • Winthrop122 Properties
  • Westport121 Properties
  • Ipswich117 Properties
  • West Stockbridge116 Properties
  • Hull110 Properties
  • Sheffield84 Properties
  • Manchester83 Properties
  • New Marlborough81 Properties
  • Concord80 Properties
  • Springfield67 Properties
  • Sudbury52 Properties
  • Ashburnham34 Properties
  • Cheshire27 Properties
  • Hubbardston8 Properties