Berkshire County Vacation Rentals

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Vacation Rentals in Berkshire County

Cozy Riverside Berkshires Retreat

Great Barrington MA

$284 nightly

$317 total

Jun 17 - Jun 18

Total with taxes and fees

When you stay at this vacation home in Great Barrington, you'll be on a river, within a 15-minute drive of Norman Rockwell Museum and National Shrine of the Divine Mercy.

Kitchen

Washer

The Meadows House @ Otis Ridge w/ 7-person hot tub

Otis MA

Located in Otis, this vacation home is in the mountains, a 2-minute drive from Otis Ridge and 5 minutes from Old Baldy Wildlife Sanctuary.

Hot Tub

Kitchen

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Great Barrington MA

With a stay at this vacation home, you'll be centrally located in Great Barrington, within a 10-minute drive of Monument Mountain and Housatonic River.

Hot Tub

Kitchen

Spacious Living, Covered Porch & Forest Setting | Beaver Creek by AvantStay

Stockbridge MA

With a stay at this vacation home in Stockbridge, you'll be within a 10-minute drive of National Shrine of the Divine Mercy and Tanglewood Music Center.

Kitchen

Free WiFi

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Hinsdale MA

With a stay at this vacation home in Hinsdale, you'll be within a 15-minute drive of Bas Ridge Golf Course and Crane Museum of Papermaking.

Air conditioning

Outdoor Space

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Becket MA

$337 nightly

$376 total

Jun 16 - Jun 17

Total with taxes and fees

With a stay at this vacation home in Becket (Sherwood Forest), you'll be within a 10-minute drive of Pyramid Lake and Becket Quarry.

Kitchen

Pet friendly

Imagine Being Lakeside, Kayaks/Fishing/EV Charger

Lenox MA

When you stay at this vacation home in Lenox, you'll be near the beach, within a 15-minute drive of Tanglewood Music Center and National Shrine of the Divine Mercy.

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

Great Barrington MA

Located in Great Barrington, this vacation home is in a rural location, within a 5-minute drive of W.E.B. Du Bois Boyhood Homesite and Mahaiwe Performing Arts Center.

Pool

Kitchen

Great Barrington, Cabin Sleeps 14, Walk To Town

Great Barrington MA

A stay at this vacation home places you in the heart of Great Barrington, within a 10-minute walk of Housatonic River Walk and Housatonic River.

Kitchen

Washer

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Egremont MA

Located in Egremont, this vacation home is in a rural location, within a 10-minute drive of W.E.B. Du Bois Boyhood Homesite and Mount Everett State Reservation.

Kitchen

Washer

5 Minutes from The Appalachian Trail and Mount Washington. In the Berkshires!

Egremont MA

When you stay at this vacation home in Great Barrington, you'll be in the mountains, within a 5-minute drive of Catamount Ski Area and Catamount Aerial Adventure Park.

Hot Tub

Kitchen

Berkshires Lakefront Retreat

Becket MA

With a stay at this vacation home in Becket (Sherwood Forest), you'll be within a 15-minute drive of Pyramid Lake and Jacob's Pillow.

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.