Great Barrington vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

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Popular amenities for Great Barrington vacation rentals

Stay near Great Barrington's top sights

Ski Butternut218 locals recommend
Theory Wellness: Recreational and Medical Marijuana Dispensary MA10 locals recommend
Monument Mountain Reservation112 locals recommend
Xicohtencatl Restaurant52 locals recommend
GB Eats32 locals recommend
The Bistro Box47 locals recommend

Other great vacation rentals in Great Barrington

Guest favorite
Bungalow in Hillsdale
Copake Lake & Catamount/Berkshires Cottage
Apr 20 – 27
$93 per night
4.86 out of 5 average rating, 129 reviews
Guest favorite
Home in Great Barrington
Elegant Year-Round Lakeside Retreat with AC
Oct 24 – 31
$386 per night
4.96 out of 5 average rating, 136 reviews
Guest favorite
Cottage in Hillsdale
Cozy Cottage Catamount, Berkshires Walk to Brewery
Jul 11 – 18
$120 per night
4.94 out of 5 average rating, 171 reviews
Guest favorite
Home in Egremont
A sunny, quiet chalet beautifully decorated.
Aug 10 – 17
$441 per night
4.97 out of 5 average rating, 113 reviews
Guest favorite
Guest suite in Austerlitz
Rustic-Modern Studio - Near Hudson, Chatham, & GB
Jun 8 – 15
$68 per night
4.86 out of 5 average rating, 136 reviews
Guest favorite
Home in New Lebanon
The old sawmill from 1771
Dec 1 – 8
$125 per night
4.99 out of 5 average rating, 347 reviews
Guest favorite
Tiny home in Chatham
Tiny House on 70 Private Acres in Hudson Valley
Jul 31 – Aug 7
$133 per night
4.99 out of 5 average rating, 176 reviews
Guest favorite
Chalet in Otis
Mid-Century Glass Octagon in the Berkshires
Nov 15 – 22
$352 per night
4.94 out of 5 average rating, 345 reviews

Other great vacation rentals in Great Barrington

Guest favorite
Guesthouse in Great Barrington
Studio in Bucolic Berkshire Setting
Apr 13 – 20
$120 per night
4.97 out of 5 average rating, 90 reviews
Guest favorite
Apartment in Great Barrington
Lush Setting, Private Deck, Queen Bed in GB
Dec 20 – 27
$98 per night
4.86 out of 5 average rating, 64 reviews
Guest favorite
Home in Great Barrington
Granite Ledge, Modern home in a unique setting
Dec 6 – 13
$420 per night
5.0 out of 5 average rating, 59 reviews
Guest favorite
Home in Great Barrington
Sunsets On Blue Hill, Newly Renovated Farmhouse
Sep 10 – 17
$462 per night
4.97 out of 5 average rating, 30 reviews
Guest favorite
Home in Great Barrington
Charming, view, large deck, private/walk downtown
Nov 26 – Dec 3
$422 per night
4.94 out of 5 average rating, 53 reviews
Guest favorite
Home in Great Barrington
Waterfront Modern Lake Mansfield Retreat
Jun 7 – 14
$713 per night
4.97 out of 5 average rating, 37 reviews
Guest favorite
Apartment in Canaan
Mountain View Getaway
Jan 10 – 17
$91 per night
5.0 out of 5 average rating, 81 reviews
Guest favorite
Apartment in Great Barrington
Walk Everywhere! | Relax in Easy Elegance!
Apr 3 – 10
$245 per night
5.0 out of 5 average rating, 92 reviews

Quick stats about vacation rentals in Great Barrington

Total rentals

240 properties

Rentals with dedicated workspaces

130 properties have a dedicated workspace

Rentals with a pool

30 properties have a pool

Pet-friendly rentals

120 properties allow pets

Family-friendly rentals

170 properties are a good fit for families

Total number of reviews

8.1K reviews

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Great Barrington?

    Yes! Work meets play with ease at over 130 vacation rentals in Great Barrington featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Great Barrington?

    Four-legged friends are welcome in Great Barrington. Choose from more than 120 vacation rentals for guests traveling with pets.

  • Are there Great Barrington vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 30 vacation homes with pools in Great Barrington, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in house rentals in Great Barrington?

    Experience the best of Great Barrington with our house rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there family-friendly house rentals in Great Barrington?

    Great Barrington has more than 140 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Great Barrington have a gym?

    Absolutely! We offer over 10 house rentals with a gym in Great Barrington. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Great Barrington have air conditioning?

    Absolutely! We offer over 30 apartment rentals with air conditioning in Great Barrington. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Great Barrington have a bbq area?

    Absolutely! We offer over 10 apartment rentals with a bbq area in Great Barrington. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Great Barrington have wifi?

    Absolutely! We offer over 40 apartment rentals with wifi in Great Barrington. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Great Barrington?

    Enhance your stay in our House Rentals with the most popular amenities: over 130 homes with air conditioning, over 150 homes with wifi, over 90 homes with a bbq area, over 10 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore