The Berkshires Vacation Rentals

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Vacation Rentals in The Berkshires

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Stockbridge MA

With a stay at this vacation home in West Stockbridge, you'll be within a 5-minute drive of Tanglewood Music Center and Stockbridge Bowl.

Cozy Riverside Berkshires Retreat

Great Barrington MA

$284 nightly

$317 total

Sep 1 - Sep 2

Total with taxes and fees

Located in Great Barrington, this vacation home is on a river, a short 4-minute walk from Monument Mountain Reservation and within 1 minutes by car from Housatonic River.

Amazing Backyard Escape, 10 Minutes from Stockbridge | Cordelia by AvantStay

Lee MA

With a stay at this vacation home in Lee, you'll be within a 15-minute drive of Tanglewood Music Center and Greenock Country Club.

Peace and quiet on the lake

Becket MA

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

Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10

Stockbridge MA

With a stay at this vacation home in Stockbridge, you'll be within a 10-minute drive of Tanglewood Music Center and Berkshire Botanical Garden.

Kitchen

Washer

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Hinsdale MA

With a stay at this vacation home in Hinsdale, you'll be steps from Ashmere Lake and a 4-minute drive from Bas Ridge Golf Course.

Air conditioning

Outdoor Space

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.

Antique Farmhouse Totally Restored

Sheffield MA

Located in Sheffield, this vacation home is in a rural location, within a 5-minute drive of Mount Riga State Park and Mount Everett State Reservation.

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Great Barrington MA

Located in Great Barrington, this vacation home is within a 5-minute drive of Ski Butternut and Lake Buel.

Mid Century Modern 4 bedroom home with sweeping mountain views in Williamstown

Williamstown MA

With a stay at this vacation home in Williamstown, you'll be a 2-minute drive from Green Mountain National Forest and 7 minutes from Farm Museum.

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Becket MA

$355 nightly

$397 total

Aug 26 - Aug 27

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 Jacob's Pillow.

Spacious waterfront Berkshire home family private get-away

Otis MA

When you stay at this vacation home in Otis, you'll be on a lake, within a 5-minute drive of County Beach and Otis Reservoir.

Kitchen

Washer

Don't see what you're looking for?

See all available properties in The Berkshires

View all properties

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.