Choose from 138 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

The view from the street
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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Property view
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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Property view
4.6
Outstanding(67 Reviews)
Bed and Breakfast
 in Great Barrington
Wainwright Inn
Garden · Kitchen / Kitchenette · Air conditioner

Bed and Breakfast in Great Barrington, for $172 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

$$$$
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Property view
5.0
Outstanding(92 Reviews)
Cottage
 in New Marlborough
Quiet rustic cottage with shared lake access
6 guests · 2 bedrooms · 1 bath
Garden · Kitchen / Kitchenette · Air conditioner

Nestled in Great Barrington, this Cottage is perfect for your next vacation. Enjoy Quiet rustic cottage with shared lake access's top-rated amenities, including Air conditioner, Dishwasher and Fireplace, and more.

$$$$
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Search by amenity

Explore vacation rentals with the most popular amenities in Great Barrington

Vacation rentals with internet & wifi in Great Barrington

Exterior
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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New Marlborough Vacation Rental | 2BR | 1BA | 850 Sq Ft | 2 Steps for Access
5.0
Outstanding(60 Reviews)
Cottage
 in New Marlborough
Waterfront Cottage: 10 Min to Great Barrington!
2 guests · 2 bedrooms · 1 bath
Kitchen / Kitchenette · Internet / Wifi · Parking

Looking for a memorable stay in Great Barrington? Our Cottage might just be what you're looking for. Enjoy amenities including Internet / Wifi, Balcony / Patio and Kitchen / Kitchenette, and more during your stay.

$$$$
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Spacious modern kitchen
4.9
Outstanding(56 Reviews)
House
 in New Marlborough
Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm.
12 guests · 5 bedrooms · 3 baths
Garden · Pets allowed · Kitchen / Kitchenette

Discover the beauty of Great Barrington with a stay at Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm., a top rated House with amenities such as Air conditioner, Dishwasher and Fireplace, and more.

$$$$
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Property view
3.9
Good(511 Reviews)
Hotel
 in Great Barrington
2star
Quality Inn
Air conditioner · Internet / Wifi · Parking

The best choice in Great Barrington for Hotel, for $172 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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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.

Frequently asked questions

What is the price range for rentals in Great Barrington?

Vacation rentals in Great Barrington have a price range between $64-$6,645. The average price for rentals in Great Barrington is $350 per night.

What are the most popular vacation rental amenities in Great Barrington?

  • Internet / Wifi
  • Kitchen / Kitchenette
  • TV

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