Vacation Rentals in Great Barrington, MA

5 BD, 3 Baths, sleeps 12 - the pool is open & a few openings for Summer 2024 !

12 guests · 5 bedrooms · 3 baths

Garden · Pool · Kitchen / Kitchenette

Nestled in Great Barrington, this House is perfect for your next vacation. Enjoy 5 BD, 3 Baths, sleeps 12 - the pool is open & a few openings for Summer 2024 !'s top-rated amenities, including Air conditioner, Dishwasher and Fireplace, and more.

$$$$

3.9

Good(206 Reviews)

Motel

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.

$$$$

4.1

Excellent(289 Reviews)

Hotel

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.

$$$$

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

Most favorited

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.

$$$$

Search by property type

Search by amenity

Explore vacation rentals with the most popular amenities in Great Barrington

Vacation rentals with internet & wifi in Great Barrington

4.9

Outstanding(67 Reviews)

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.

$$$$

5.0

Outstanding(56 Reviews)

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.

$$$$

5.0

Outstanding(71 Reviews)

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.

$$$$

3.9

Good(216 Reviews)

Motel

The Briarcliff Motel

Garden · Pool · Pets allowed

When traveling to Great Barrington, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $80 per night.

$$$$