Great Barrington Vacation Rentals

Our Favorite Vacation Rentals in Great Barrington

RiverSong Suite In The Berkshires
Excellent1br Home/Apartment
HolidayLettingsFrom $256
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Tanglewood / Berkshires - 2 Bed 2 Bath Apartment
2br Home/Apartment
HolidayLettingsFrom $480
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NEW! Monterey Home w/Porch by Beach & State Parks!
3br Home/Apartment
HolidayLettingsFrom $453
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Overnight at Althouse -Higgins
Excellent2br Home/Apartment
HolidayLettingsFrom $229
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Berkshire Getaway ~ Romantic Tower Suite on Storybook Estate
1br Home/Apartment
HolidayLettingsFrom $303
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Total Privacy! Tanglewood Retreat With Berkshire Views!
5br Home/Apartment
HolidayLettingsFrom $816
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Charming and Spacious Colonial Farmhouse on 4 Acre Estate
4br Farmhouse
HolidayLettingsFrom $569
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Private En Suite in Beautiful Victorian
Excellent1br Home/Apartment
AirbnbFrom $127
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See all 386 deals in Great Barrington

Great Barrington Vacation Rentals with a Pool

Berkshires Rustic Retreat (close to everything!)
Excellent1br Home/Apartment
AirbnbFrom $158
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Private Berkshire Getaway
Excellent3br Other
AirbnbFrom $678
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Race Mountain House
Excellent4br Home/Apartment
AirbnbFrom $989
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Berkshire Valley Retreat
5br Home/Apartment
AirbnbFrom $1113
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Great Barrington Vacation Rentals with Wi-Fi

GB River View
Excellent2br Home/Apartment
AirbnbFrom $184
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Apartment Retreat, Housatonic House on the Hill
Excellent2br Home/Apartment
AirbnbFrom $147
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One Bedroom Flat @ Monument Mountain
Excellent1br Home/Apartment
AirbnbFrom $249
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Charming Rustic Cabin
Excellent4br Cabin
AirbnbFrom $537
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Great Barrington Pet-Friendly Vacation Rentals

KNOB HILL, GREAT BARRINGTON, MA
Excellent3br Home/Apartment
AirbnbFrom $396
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Cottage on Scenic Road
Excellent1br Home/Apartment
AirbnbFrom $181
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Spacious 2 BR Berkshires Guest Hse
Excellent2br Home/Apartment
AirbnbFrom $198
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Beautiful Berkshire Farmhouse on 160+ Acres
Excellent7br Home/Apartment
AirbnbFrom $961
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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.

Price and Availability in Great Barrington

Most expensive

Most availability

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 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 Weather in Great Barrington

SEE FULL WEATHER FORECAST:

93º 46º

4.68

90º 51º

8.25

89º 40º

6.89

79º 27º

2.84

64º 0º

6.39

59º 9º

3.94

61º -10º

4.66

73º -3º

4.09

55º 7º

2.35

67º 18º

3.63

86º 40º

2.56

91º 42º

3.42

Jul

Aug

Sep

Oct

Nov

Dec

Jan

Feb

Mar

Apr

May

Jun

Rainy days

SEE FULL WEATHER FORECAST:

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 January, when temperatures drop to -10 ˚F. The wettest month in Great Barrington is August with 8.25 inches of rain, while the driest month is March with 2.35 inches of rain.

What Expert Travelers Think

— Packed full of information, from the best time of year to visit (I love NYC in Spring) to top tips from locals, All The Rooms provides the best accommodation, whether you are looking to enjoy your first time visit to New York or want to experience a new location
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The Life of a Social Butterfly
— Whenever I am making travel plans I always use comparison sites to find the best accommodation for us at the best price. Whether it be for hotel stays or private rentals AllTheRooms makes this so much easier and quicker as it brings all my searches into one place, with a great offering of options
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Visit Tammymum
— I use and I recommend AllTheRooms because it is a complete platform. It helps to save a lot of time, it gives all the main information about price, location, and features. In a few steps, I can easily find the best place to stay according to my criteria.
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Vacation Rentals in Great Barrington

Browse accommodations from all the best providers including Airbnb, Priceline, Bed and Breakfast and more at AllTheRooms.com. AllTheRooms has 386 rentals, hotels and other great places to stay during your time in Great Barrington, with everything from inexpensive hostels and homestays to extravagant Airbnbs and hotels. If you are trying to keep costs down, the cheapest place to stay in Great Barrington is only $10 a night. The average price of an accommodation is $321 per night.

Those looking to get some work done during their trip to Great Barrington can choose from 228 places to stay that include WiFi. 31 places to stay include a breakfast. Choose from 14 places to stay that provide gym options, so you won't miss a single workout. Driving to Great Barrington? Then choose one of the 226 places to stay that comes with a parking spot included. We have 24 places to stay that have a pool or jacuzzi.

Those traveling with a cat, dog or some other animal can stay in any of 70 accommodations that are designated as pet-friendly.

AllTheRooms aggregates vacation rentals, hotels and other bespoke accommodation types from many providers in Great Barrington, including 170 places to stay from Airbnb, 4 accommodations from Priceline and 3 places to stay from Bed and Breakfast

267 of our places to stay in Great Barrington have been rated by previous guests. They rated 73% as great. 81 places to stay in are instantly bookable.