Great Barrington Vacation Rentals

Our Favorite Vacation Rentals in Great Barrington

  • The Old Inn On The Green
    Good11br 4-star Home/Apartment
    Booking.com
    From
    $260
  • The Smith Farm Homestead
    ExcellentHome/Apartment
    HolidayLettings
    From
    $175
  • Tentrr - Hillsdale Hideaway
     Country House
    Booking.com
    From
    $133
  • Lakefront Berkshires Ski/Summer House, Great Views
    Nice4br Home/Apartment
    HolidayLettings
    From
    $457
  • Zen Cottage in the Woods
     3br Home/Apartment
    HolidayLettings
    From
    $380
  • RiverSong Suite In The Berkshires
    ExcellentHome/Apartment
    HolidayLettings
    From
    $256
  • Picturesque 19th century home on 3 private acres
     4br Home/Apartment
    HolidayLettings
    From
    $272
  • Villa with Access to 2 Pools, a Hot Tub, an 18-Hole Mini Golf Course, and More
     Villa
    HolidayLettings
    From
    $197

Check prices for these upcoming dates

Great Barrington Vacation Rentals with a Pool

  • Charming Berkshires Cottage
    ExcellentHome/Apartment
    Airbnb
    From
    $249
  • Field View House.
    Excellent4br Home/Apartment
    Airbnb
    From
    $678
  • Berkshires Rustic Retreat (close to everything!)
    ExcellentHome/Apartment
    Airbnb
    From
    $158
  • Modern Country Home Near Berkshire Cultural Venues
    Good4br Home/Apartment
    Airbnb
    From
    $961

Great Barrington Vacation Rentals with Wi-Fi

  • Private En Suite in Beautiful Victorian
    ExcellentHome/Apartment
    Airbnb
    From
    $141
  • "The Secret O' Life"
    Excellent3br Home/Apartment
    Airbnb
    From
    $223
  • Former Sunset View Inn
    Excellent5br Home/Apartment
    Airbnb
    From
    $424
  • Heart of GB Walk to Town Sunny Retreat!
    Excellent2br Home/Apartment
    Airbnb
    From
    $347

Great Barrington Pet-Friendly Vacation Rentals

  • Best vacation home in Berkshires (Summer & rest of seasons ..1, 2 or 3 families)
     6br Home/Apartment
    HolidayLettings
    From
    $998
  • Cozy Modern Condo for the Berkshires
     2br Home/Apartment
    HolidayLettings
    From
    $393
  • Garfield House
     2br Home/Apartment
    HolidayLettings
    From
    $265
  • Best Vacation Home in Berkshires..(Winter & rest of seasons 1, 2, or 3 families)
     6br Home/Apartment
    HolidayLettings
    From
    $998

Great Barrington Travel Guide

Visitors come to Great Barrington all year round, with everything from skiing and hiking to art museums and shopping opportunities. Great Barrington is a town that is found in Berkshire County, Massachusetts and is known as one of the best small towns in the United States. Skiing is particularly popular, with Ski Butternut being popular in the winter. Antique shopping is big in Great Barrington and there is even a huge Antiques Center in the town. When it comes to dining, foodies will not be disappointed -- there is everything from sweat treats to cheap seats to fine dining experiences.

Things to Do in Great Barrington

One of the best places to go hiking in Great Barrington is at Monument Mountain. Visitors can explore the trails, as well as enjoy views of the Housatonic River Valley from up above. Hikers can also enjoy the Housatonic River Walk alongside the river. At Lake Mansfield there is the opportunity to relax and enjoy the town's beachy area. There are life guards here in peak season, making it a great opportunity to go swimming. In the winter, Ski Butternut Resort attracts active vacationers. It is found in the Warner Mountain and is home to lots of fun trails and ski lifts, as well as a tubing area.

Best Time to Visit Great Barrington

The summer time is the best time in Great Barrington for hiking. The winter offers the best opportunity for skiing.

Price and Availability in Great Barrington

Most expensive
Most availability
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The cheapest day to stay at a vacation rental in Great Barrington tends to be Thursday, while the most expensive day tends to be Saturday. Vacation homes in Great Barrington 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 Great Barrington is in July, while the cheapest month is in March. The most popular time to book a vacation rental in Great Barrington is in the high season in August. Great Barrington has its low season in April, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Great Barrington

Rainy days
64°
6
59°
4
61° -10°
5
73° -3°
4
55°
2
67° 18°
4
86° 40°
3
91° 42°
3
93° 46°
5
90° 51°
8
89° 40°
7
79° 27°
3
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Rainy days

This climate histogram shows you the weather patterns in Great Barrington. The warmest months in Great Barrington are June and July, when temperatures reach 93 ˚F. The coolest month is December, when temperatures drop to -10 ˚F. The wettest month in Great Barrington is May with 8.25 inches of rain, while the driest month is October with 2.35 inches of rain.

What Expert Travelers Think

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Vacation Rentals in Great Barrington

At AllTheRooms.com we have vacation rentals from all of your favorite providers - Airbnb, Priceline, Bed and Breakfast and many more. Great Barrington has 450 hotels, vacation rentals and other special places to stay, with prices to suit budget travelers, luxury travelers and everything in between. For those traveling on a budget, the most economical place to stay in Great Barrington is available at $22 per night. A typical rental in Great Barrington costs on average $313 a night.

Those needing to get some work done during their trip to Great Barrington can pick from 208 places to stay that have WiFi. 34 places to stay include a breakfast. Choose from 6 places to stay that provide gym options, so you don't miss a single workout. Driving to Great Barrington? Then choose one of the 203 places to stay that comes with a parking spot included. We have 27 vacation rentals that have a pool or jacuzzi.

Those traveling with a dog, cat or some other animal can stay in one of 60 accommodations that are designated as pet-friendly.

We combine a wide variety of Great Barrington accommodations including vacation rentals, home stays, hostels and other unique places to stay into one easy search. We show results from more than 4 providers, including 194 places to stay from Airbnb, 4 accommodations from Priceline and 3 places to stay from Bed and Breakfast.

303 accommodations in Great Barrington have been reviewed; 73% are rated highly. 106 accommodations allow instant booking.

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