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Great Barrington vacation rentals

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Great Barrington vacation rentals

Gym
BBQ grill
Laptop-friendly workspace
Wifi
Air conditioning

Stay near Great Barrington's top sights

Guido's Fresh Marketplace248 locals recommend
Ski Butternut218 locals recommend
The Prairie Whale203 locals recommend
Baba Louie's Sourdough Pizza121 locals recommend
Monument Mountain Reservation112 locals recommend
Mahaiwe Performing Arts Center102 locals recommend

Other great vacation rentals in Great Barrington

Guest favorite

Home in Athens

5 out of 5 average rating, 34 reviews

Perfect home for a getaway from NYC

Superhost

Home in Albany

4.67 out of 5 average rating, 12 reviews

CasitaCosita

Guest favorite

Home in Millerton

4.97 out of 5 average rating, 153 reviews

Vacation Home In Millerton

Guest favorite

Home in Monroe

4.9 out of 5 average rating, 10 reviews

The Camp

Guest favorite

Home in Canaan

5 out of 5 average rating, 11 reviews

Luxury/pool/private Villa Mariana Blackberry River

Guest favorite

Cottage in Canaan

4.98 out of 5 average rating, 86 reviews

The Cottage at Great Falls Luxury Getaway.

Guest favorite

Farm stay in Averill Park

4.96 out of 5 average rating, 49 reviews

Modern Country Farmhouse, Walking Distance to Lake

Guest favorite

Home in Canaan

4.96 out of 5 average rating, 25 reviews

Black Friday Sale Mountain/Lake View in Canaan, NY

Show all

Quick stats about vacation rentals in Great Barrington

  • Total rentals

    250 properties

  • Total number of reviews

    9.9K reviews

  • Family-friendly rentals

    180 properties are a good fit for families

  • Pet-friendly rentals

    120 properties allow pets

  • Rentals with a pool

    20 properties have a pool

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

Frequently Asked Questions

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

    Yes! Work meets play with ease at over 150 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 20 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 apartment rentals in Great Barrington?

    Experience the best of Great Barrington with our apartment rentals, starting at about $40 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 house rentals in Great Barrington have air conditioning?

    Absolutely! We offer over 140 house rentals with air conditioning in Great Barrington. Enjoy a tailored experience with all the comforts you desire.

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

    Absolutely! We offer over 20 cabin rentals with a bbq area in Great Barrington. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Great Barrington have wifi?

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

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

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 40 homes with air conditioning, over 40 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

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