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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 Old Inn On The Green
    Good11br 4-star Home/Apartment
    Booking.com
    From
    $260
  • Gem of the Berkshires, walk to downtown & lake.
    Excellent5br Home/Apartment
    HolidayLettings
    From
    $799
  • Spacious Villa with Access to Pools, a Hot Tub, Mini Golf, and a Sauna!
     2br Villa
    RedAwning
    From
    $245
  • 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
    $220
  • Lakefront Berkshires Ski/Summer House, Great Views
    Nice4br Home/Apartment
    HolidayLettings
    From
    $587
  • Zen Cottage in the Woods
     3br Home/Apartment
    HolidayLettings
    From
    $380
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Great Barrington Vacation Rentals with a Pool

  • Charming Berkshires Cottage
    ExcellentHome/Apartment
    Airbnb
    From
    $249
  • A Fun Farmhouse
    Excellent4br Farm Stay
    Airbnb
    From
    $593
  • Idyllic Berkshires Getaway
    Excellent4br Home/Apartment
    Airbnb
    From
    $390
  • Country Castle with indoor pool and MORE, sleeps 12+
     5br Home/Apartment
    Airbnb
    From
    $1,582
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Great Barrington Vacation Rentals with Wi-Fi

  • "The Secret O' Life"
    Excellent3br Home/Apartment
    Airbnb
    From
    $218
  • Former Sunset View Inn
    Excellent5br Home/Apartment
    Airbnb
    From
    $424
  • Sunny Solar Home in Downtown Gt Barrington
    Excellent3br Home/Apartment
    Airbnb
    From
    $203
  • The Hemlock House - 1.5mi to downtown GB
    Excellent3br Home/Apartment
    Airbnb
    From
    $396
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Great Barrington Pet-Friendly Vacation Rentals

  • Cozy Berkshire Home, 1 Mile to Stockbridge Center!
     4br Home/Apartment
    HolidayLettings
    From
    $387
  • Hillhouse Log Cabin
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $487
  • Cozy Stockbridge Home - Walk To Golf Course!
     2br Home/Apartment
    HolidayLettings
    From
    $401
  • Berkshire Farmhouse Vacation
    Excellent5br Farmhouse
    HolidayLettings
    From
    $386
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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
60° -5°
3
67° 1°
1
74° 19°
5
83° 36°
4
85° 39°
5
90° 51°
4
54° -11°
5
85° 34°
3
73° 29°
8
66° 11°
4
53° 1°
5
54° -11°
5
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Jan
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 90 ˚F. The coolest month is May, when temperatures drop to -11 ˚F. The wettest month in Great Barrington is March with 8.3 inches of rain, while the driest month is October with 1.25 inches of rain.

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What Expert Travelers Think

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  • — 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
    Visit Coco Travels

Vacation Rentals in Great Barrington

Pick the perfect rental for your trip at AllTheRooms.com. We compare Airbnb, Priceline, Agoda and more. AllTheRooms has 403 vacation rentals, hotels and other great places to stay during your time in Great Barrington, with everything from cheap hostels and homestays to luxury Airbnbs and hotels. If you are wanting to save money, the lowest priced place to stay in Great Barrington comes in at $12 per night. An average vacation rental in Great Barrington costs on average $288 a night.

If you have to have an internet connection during your stay in Great Barrington, then you can choose from over 203 places to stay that provide WiFi internet. 32 places to stay include a breakfast. You can maintain your workout regime by staying at one of 6 accommodations that provide gym facilities. If you're planning on getting to Great Barrington by car, be sure to choose from 200 accommodations that provide parking. We track 26 accommodations that have a pool or jacuzzi.

If you're traveling with your best friend, then make sure to select one of the 53 pet-friendly accommodations available.

284 of the rentals in Great Barrington have been reviewed by previous guests. They rated 72% as excellent or good. You can instantly book any of 105 places to stay right now.

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