Great Barrington, MA Vacation Rentals

Choose from 139 vacation rentals located in Great Barrington, Massachusetts. Top filters in Great Barrington include Internet / Wifi, Kitchen / Kitchenette, and TV. Prices range from $64 to $6,645 per night. Our most popular vacation rental types near Great Barrington are Condo and Hotel.

Top vacation rentals in Great Barrington

4.9

Outstanding(118 Reviews)

House

in Great Barrington

A perfect getaway year-round. Booking for the rest of '23 and through '24!

12 guests · 5 bedrooms · 3 baths

Garden · Pool · Kitchen / Kitchenette

Nestled in Great Barrington, this House is perfect for your next vacation. Enjoy A perfect getaway year-round. Booking for the rest of '23 and through '24! 's top-rated amenities, including Air conditioner, Dishwasher and Fireplace, and more.

$$$$

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3.5

Average(198 Reviews)

Motel

in Great Barrington

Travelodge by Wyndham Great Barrington Berkshires

Pool · Kitchen / Kitchenette · Air conditioner

Experience vacation in Great Barrington with our Motel, Travelodge by Wyndham Great Barrington Berkshires. Enjoy amenities such as Air conditioner, Internet / Wifi and Laundry, and more.

$$$$

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3.9

Good(196 Reviews)

Motel

in Great Barrington

Monument Mountain Motel

Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Are you ready to indulge in a relaxing getaway? Our Motel in Great Barrington has everything you need for a rejuvenating stay. Treat yourself to Monument Mountain Motel's exceptional amenities, such as Air conditioner, Internet / Wifi and Kitchen / Kitchenette.

$$$$

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4.5

Excellent(211 Reviews)

Hotel

in Great Barrington

3star

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Pool · Kitchen / Kitchenette · Air conditioner

Experience the best of Great Barrington with this Hotel available for $67. This property is equipped with amenities including Air conditioner, Fireplace and Internet / Wifi, and more.

$$$$

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Explore vacation rentals with the most popular amenities in Great Barrington

Vacation rentals with internet & wifi in Great Barrington

4.9

Outstanding(65 Reviews)

House

in Great Barrington

Location Location! Comfort and Privacy So Close to Downtown

10 guests · 5 bedrooms · 2 baths

Garden · Kitchen / Kitchenette · Air conditioner

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Great Barrington, at $500 per night for your next great vacation.

$$$$

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5.0

Outstanding(71 Reviews)

House

in Monterey

Gorgeous Log Cabin in the Berkshires -- Perfect All Year Long.

8 guests · 3 bedrooms · 4 baths

Garden · Kitchen / Kitchenette · Air conditioner

Indulge in a peaceful retreat at Gorgeous Log Cabin in the Berkshires -- Perfect All Year Long., our elegant House in Great Barrington. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more.

$$$$

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4.7

Outstanding(24 Reviews)

Bed and Breakfast

in Great Barrington

The Barrington

Kitchen / Kitchenette · Air conditioner · Internet / Wifi

This Bed and Breakfast in Great Barrington, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

$$$$

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4.1

Excellent(313 Reviews)

Hotel

in Great Barrington

2star

Holiday Inn Express Great Barrington, an IHG Hotel

Pool · Kitchen / Kitchenette · Air conditioner

Looking for the perfect place to call home during your trip to Great Barrington? This Hotel offers a comfort and style with top-notch amenities, including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$

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Great Barrington

Great Barrington travel guide

Let us help you plan your perfect Great Barrington vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Great Barrington, and more.