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Great Barrington Vacation Rentals

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Our Favorite Vacation Rentals in Great Barrington

  • 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
  • Country Elegance in the Berkshires
    Excellent4br Home/Apartment
    HolidayLettings
    From
    $959
  • Spacious Villa with Access to Pools, a Hot Tub, Mini Golf, and a Sauna!
     2br Villa
    RedAwning
    From
    $195
  • The Old Inn On The Green
    Good11br 4-star Home/Apartment
    Booking.com
    From
    $385
  • The Smith Farm Homestead
    ExcellentHome/Apartment
    HolidayLettings
    From
    $175
  • Villa with Access to Pools, a Hot Tub, Mini Golf, and a Sauna! Great Location!
     2br Villa
    RedAwning
    From
    $176
  • Tentrr - Hillsdale Hideaway
     Country House
    Booking.com
    From
    $115
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Great Barrington Vacation Rentals with a Pool

  • Charming Berkshires Cottage
    ExcellentHome/Apartment
    Airbnb
    From
    $249
  • Field View House.
    Excellent4br Home/Apartment
    Airbnb
    From
    $565
  • Idyllic Berkshires Getaway
    Excellent4br Home/Apartment
    Airbnb
    From
    $367
  • Treetops: Indoor pool & only 10 min to Catamount!!
    Excellent5br Home/Apartment
    Airbnb
    From
    $1,271
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Great Barrington Vacation Rentals with Wi-Fi

  • Private En Suite in Beautiful Victorian
    ExcellentHome/Apartment
    Airbnb
    From
    $127
  • KNOB HILL, GREAT BARRINGTON, MA
    Excellent3br Home/Apartment
    Airbnb
    From
    $396
  • Former Sunset View Inn
    Excellent5br Home/Apartment
    Airbnb
    From
    $480
  • Great Barrington Getaway House
    Excellent3br Home/Apartment
    Airbnb
    From
    $381
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Great Barrington Pet-Friendly Vacation Rentals

  • Lakefront Berkshires Ski/Summer House, Great Views
    Nice4br Home/Apartment
    HolidayLettings
    From
    $304
  • Fabulous NEW Spacious House in the Berkshires Tanglewood
     4br Home/Apartment
    HolidayLettings
    From
    $408
  • Hillhouse Log Cabin
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $487
  • Berkshire Farmhouse Vacation
    Excellent5br Farmhouse
    HolidayLettings
    From
    $342
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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.

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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.
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The Weather in Great Barrington

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 Great Barrington. The hottest month in Great Barrington is June, when temperatures peak at 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.

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What Expert Travelers Think

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    Max HobbsLTL Mandarin School
    LTL Mandarin School

  • — Site is easy to use; clean, laid out well, good colors and branding, fun logo and title that connects to the purpose of the brand. The blog, vacation destinations, and rental destinations is a great feature and really make the brand stand apart from other sites!

    Laurelle McVicker
    Laurelle McVickerLaurelle McVicker
    Laurelle McVicker

Vacation Rentals in Great Barrington

At AllTheRooms.com we have vacation rentals from all of your favorite providers - Airbnb, Priceline, Bed and Breakfast and more. Great Barrington has 437 hotels, vacation rentals and other unique places to stay, with prices to suit careful travellers, luxury travelers and everything in between. When traveling on a budget, the most economical place to stay in Great Barrington is available at $20 per night. In general, a place to stay in Great Barrington will cost you $318 per night.

If you need an internet connection during your stay in Great Barrington, then you can choose from over 250 accommodations that have WiFi internet. 34 places to stay include a morning meal. Fitness addicts can get a workout in during their stay by choosing from 15 accommodations that have gym facilities. If you're planning on arriving in Great Barrington by car, be sure to choose from 242 accommodations that provide parking. We have 25 places to stay that have a pool or jacuzzi.

If you're traveling with your best friend, then make sure to choose one of the 79 pet-friendly accommodations available.

In Great Barrington AllTheRooms currently compares hotels, vacation rentals, hostels from more than 4 providers, including 183 places to stay from Airbnb, 3 accommodations from Priceline and 3 places to stay from Bed and Breakfast.

303 accommodations in Great Barrington have been reviewed; 74% are rated highly. 102 accommodations allow instant booking.

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