Stockbridge, MA Vacation Rentals

Check prices for these upcoming dates

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
64°
1
56° -4°
3
70° 13°
3
63° 26°
4
86° 29°
2
91° 37°
3
93° 55°
4
88° 45°
3
83° 29°
5
76° 18°
3
74° 18°
4
61° -4°
3
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
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 January, when temperatures drop to -4 ˚F. The wettest month in Stockbridge is April with 5.15 inches of rain, while the driest month is December with 1.29 inches of rain.

What Expert Travelers Think

  • — I love All the Rooms because instead of having to check one place for home rentals, another for hotel, another for bed and breakfasts, and yet another for a room rental in a private residence, I can finally see EVERYTHING at one site; saving me considerable time

    Jeff Campbell
    Jeff CampbellMiddle Class Dad
  • — 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
  • — My favorite thing about AllTheRooms is that it combines both rentals and hotels available so you can see an entire view of what is available in a certain area. I was able to see listings on AllTheRooms that I never even saw on other travel sites!

    Daniella Flores
    Daniella FloresILIKETODABBLE

Vacation Rentals in Stockbridge

At AllTheRooms.com we have rentals from all of the leading providers - Airbnb, Priceline, Agoda and many more. AllTheRooms has 246 rentals, hotels and other great places to stay while you enjoy Stockbridge, with everything from budget hostels and homestays to luxury Airbnbs and hotels. For those traveling on a budget, the cheapest place to stay in Stockbridge is available at $55 per night. The average price of a rental is around $665 per night.

Those looking to get some work finished during their trip to Stockbridge can choose from 84 places to stay that provide WiFi. We have 9 accommodations that come with breakfast included. You can maintain your workout routine by staying at one of 5 accommodations that provide gym facilities. If you're planning on arriving in Stockbridge by car, be sure to choose from 78 accommodations that provide parking. 12 places to stay have a a pool or jacuzzi

Those traveling with a dog, cat or some other animal can stay in one of 29 accommodations that are designated as pet-friendly.

144 of our accommodations in Stockbridge have been reviewed and rated. 75% are rated great. 64 accommodations allow instant booking.

Destinations near Stockbridge

  • Boston3,441 Properties
  • Nantucket3,241 Properties
  • Provincetown2,272 Properties
  • Eastham1,663 Properties
  • Dennis Port1,632 Properties
  • Chatham1,575 Properties
  • Brewster1,460 Properties
  • Wellfleet1,323 Properties
  • Orleans1,230 Properties
  • Oak Bluffs1,137 Properties
  • Somerville1,045 Properties
  • Edgartown1,004 Properties
  • West Yarmouth913 Properties
  • Cambridge870 Properties
  • Falmouth869 Properties
  • Mashpee859 Properties
  • Hyannis808 Properties
  • South Yarmouth791 Properties
  • Brookline765 Properties
  • Tisbury714 Properties
  • Plymouth678 Properties
  • Rockport673 Properties
  • East Falmouth670 Properties
  • West Dennis627 Properties
  • North Truro612 Properties
  • Gloucester608 Properties
  • South Chatham599 Properties
  • Lenox539 Properties
  • Harwich533 Properties
  • Worcester492 Properties
  • Salem474 Properties
  • Dennis472 Properties
  • Harwich Port463 Properties
  • East Sandwich442 Properties
  • Centerville441 Properties
  • Hancock430 Properties
  • Revere415 Properties
  • Great Barrington411 Properties
  • Vineyard Haven401 Properties
  • Waltham389 Properties
  • Lee368 Properties
  • Northampton357 Properties
  • Quincy357 Properties
  • Sandwich352 Properties
  • Newton341 Properties
  • Truro339 Properties
  • Medford326 Properties
  • Watertown323 Properties
  • Williamstown315 Properties
  • Newburyport312 Properties
  • Marblehead304 Properties
  • Pittsfield300 Properties
  • South Dennis290 Properties
  • North Falmouth267 Properties
  • Chelsea266 Properties
  • Amherst257 Properties
  • Marshfield242 Properties
  • Osterville232 Properties
  • Barnstable232 Properties
  • Arlington231 Properties
  • Wareham207 Properties
  • Scituate200 Properties
  • West Harwich198 Properties
  • Woburn186 Properties
  • Chilmark172 Properties
  • Bourne164 Properties
  • Sturbridge155 Properties
  • Fairhaven138 Properties
  • Winthrop130 Properties
  • Ipswich120 Properties
  • Westport117 Properties
  • West Stockbridge109 Properties
  • Marlborough108 Properties
  • Hull97 Properties
  • New Marlborough89 Properties
  • Sheffield81 Properties
  • Manchester76 Properties
  • Springfield65 Properties
  • Concord65 Properties
  • Sudbury48 Properties
  • Ashburnham33 Properties
  • Cheshire22 Properties
  • Hubbardston8 Properties