Great Barrington Vacation Rentals, Condos, Hotels

Choose from 130 vacation rentals located in Great Barrington, Massachusetts. Top filters in Great Barrington include kitchen / kitchenette, parking, and laundry. Prices range from $50 to $6,645 per night. Our most popular vacation rental types near Great Barrington are houses and hotels.

Top vacation rentals in Great Barrington

Browse all rentals

Hotel

The Briarcliff Motel

Booking.com

3.9

(180)

$80

Entire house

A perfect getaway year-round. Booking for the remainder of '22 and into 2023!

12 guests · 5 bedrooms · 3 baths · Vrbo

4.8

(106)

$425

Hotel

Holiday Inn Express Great Barrington, an IHG Hotel

Booking.com

4.1

(346)

$81

Hotel

Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel

Expedia

4.3

(372)

$120

Entire house

Divine Inspiration

8 guests · 4 bedrooms · 3 baths · PlumGuide

$756

Entire house

Private rustic cottage with lake access

6 guests · 2 bedrooms · 1 bath · Vrbo

5.0

(80)

$195

Hotel

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

3-Star Hotel · Booking.com

4.5

(210)

$114

Hotel

Travelodge by Wyndham Great Barrington Berkshires

Booking.com

3.6

(173)

$50

Hotel

Quality Inn

Booking.com

3.9

(486)

$180

Entire house

Just You, the frozen lake, and 2 nearby ski areas! Perfect cozy winter getaway

6 guests · 3 bedrooms · 3 baths · Vrbo

4.8

(59)

$280

Bed & breakfast

Wainwright Inn

Booking.com

4.8

(77)

$172

Rental

Thornewood Inn

Booking.com

3.9

(18)

$179

Hotel

Monument Mountain Motel

Booking.com

4.1

(168)

$60

Entire house

Gorgeous Log Cabin in the Berkshires

8 guests · 3 bedrooms · 4 baths · Vrbo

5.0

(54)

$799

Entire house

Lakefront Berkshires Retreat with Deck, Dock and Boat!

Booking.com

$310

Entire house

Rustic Berkshires Cottage at Lake Buel with Kayaks!

Booking.com

4.6

(4)

$217

Entire house

Waterfront Lake Buel Cottage 7 Mi to Monument Mtn

Booking.com

$217

Hotel

Travelodge by Wyndham Great Barrington Berkshires

Expedia

3.7

(365)

$69

Entire house

Newly Remodeled Private Estate! Pool, Tennis Court, 5 Mins to Town & Ski Resorts

12 guests · 4 bedrooms · 4 baths · Vrbo

5.0

(48)

$770

Entire house

Renovated Lakefront House with Dock Pets Welcome!

Booking.com

$217

Entire apartment

Egremont Village Inn by AvantStay

Booking.com

$168

Entire house

Half Moon by AvantStay 4BR Cabin w Large Deck Yard w Patio Outdoor Dining

Booking.com

$92

Entire house

Location Location! Comfort and Privacy So Close to Downtown

10 guests · 5 bedrooms · 2 baths · Vrbo

4.9

(49)

$428

Entire house

Spacious Berkshires Retreat about 3 Mi to Skiing!

Booking.com

$79

Entire apartment

Morgan's Millhouse (Front)

Booking.com

3.8

(4)

$81

Entire apartment

Entire home hosted by Morgan

Booking.com

3.1

(3)

$81

Patio furniture. .gas grill.. Outdoor. Yard games...cricket and bocce.

Entire house

COZY LOG HOME*The Berkshires* Hiking* Skiing**Gt. Barrington *fireplace <br>

8 guests · 2 bedrooms · 1 bath · Vrbo

4.8

(51)

$234

Rental

Tentrr Signature Site - Great Barrington Campsite - with Goats and Pool!

Booking.com

$99

Entire house

Private Home Overlooking Stevens Lake

Booking.com

$103

Entire house

Cozy Great Barrington Home about 1 Mi to Ski Resort!

Booking.com

4.3

(2)

$92

Search by property type

Browse the most popular vacation rental types in Great Barrington

Vacation rentals with a kitchen in Great Barrington

Browse all rentals

Entire house

Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm.

12 guests · 5 bedrooms · 3 baths · Vrbo

5.0

(41)

$540

Entire house

1 Mile from Butternut! Close to Lakes, Appalachian Trail, Restaurants, Theatre.

12 guests · 5 bedrooms · 3 baths · Vrbo

4.8

(41)

$575

New Marlborough Vacation Rental | 2BR | 1BA | 850 Sq Ft | 2 Steps for Access

Entire house

Waterfront Lake Buel Cottage: 7 Mi to Monument Mtn

2 guests · 2 bedrooms · 1 bath · Vrbo

5.0

(37)

$223

Entire house

Stunning Renovated Victorian

12 guests · 5 bedrooms · 5 baths · Vrbo

5.0

(39)

$1,108

Entire apartment

#2 - Nestled minutes from Main Street, Great Barrington

5 guests · 1 bedroom · 1 bath · Vrbo

4.8

(39)

$199

Entire house

Twin Maple Farm: Charming Modern Farmhouse

8 guests · 4 bedrooms · 2 baths · Vrbo

5.0

(36)

$350

Entire house

A Fun Farmhouse Near Ski Butternut

8 guests · 4 bedrooms · 3 baths · Vrbo

5.0

(31)

$350

Entire house

Romantic Berkshires Cottage - Stunning Views, Pool

3 guests · 1 bedroom · 1 bath · Vrbo

5.0

(30)

$214

The Riverhouse in Housatonic, MA. Your front door to the private upstairs apt.

Entire apartment

2 bedroom Riverhouse in the Heart of the Berkshires

4 guests · 2 bedrooms · 1 bath · Vrbo

4.9

(28)

$157

Entire apartment

Apartment in Gorgeous Stonybrook Farm

2 guests · 1 bedroom · 1 bath · Vrbo

4.7

(32)

$160

Entire house

Minutes from downtown Great Barrington, Convenient location

8 guests · 4 bedrooms · 3 baths · Vrbo

4.9

(26)

$362

Recharge with family and friends, this relaxing lounging area features leather couch that seats up to 10-12, a gas fireplace, and a 65 inch UHD smart TV.

Entire house

CHIC UPDATED DOWNTOWN Great Barrington, Sleeps 14

14 guests · 3 bedrooms · 3 baths · Vrbo

4.8

(25)

$728

Entire house

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

14 guests · 5 bedrooms · 4 baths · Vrbo

5.0

(24)

$833

Entire house

Newly Renovated Home With All The Modern Amenities

7 guests · 3 bedrooms · 2 baths · Vrbo

5.0

(23)

$350

Entire house

The Cabin at Blue Hill Retreat

2 guests · 1 bath · Vrbo

5.0

(21)

$238

Entire house

DISCOUNT INCREDIBLE LAKE FRONT HOUSE AND DOCK ON LAKE BUEL.SWIM FISH BOAT

12 guests · 6 bedrooms · 3 baths · Vrbo

4.9

(22)

$2,024

Entire house

Charming Housatonic Village Cape

10 guests · 5 bedrooms · 2 baths · Vrbo

4.8

(23)

$225

Entire house

Private Woodland Getaway

10 guests · 3 bedrooms · 3 baths · Vrbo

5.0

(20)

$559

Entire house

NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

8 guests · 3 bedrooms · 3 baths · Vrbo

5.0

(18)

$503

New Marlborough Vacation Rental | 1BR | 1BA | 750 Sq Ft | 1 Story

Entire house

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

2 guests · 1 bedroom · 1 bath · Vrbo

4.5

(21)

$297

Bed & breakfast

The Barrington

4-Star Hotel · Expedia

4.8

(81)

$265

The main view of the house from the driveway

Entire house

Idyllic Berkshire Get Away: Balance of relaxation and convenience

6 guests · 3 bedrooms · 2 baths · Vrbo

4.5

(20)

$214

Entire house

Lake Community - Near Town, Attractions

6 guests · 2 bedrooms · 1 bath · Vrbo

5.0

(14)

$172

Entire house

Cozy Berkshire home close to Lake Buel, Butternut and Great Barrington.

6 guests · 3 bedrooms · 2 baths · Vrbo

4.8

(16)

$270

A scenic retreat awaits at this Great Barrington vacation rental house!

Entire house

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

10 guests · 4 bedrooms · 2 baths · Vrbo

3.7

(30)

$315

Entire cabin

Recently Renovated, steps to Lake Buel, close to Great Barrington & Stockbridge

6 guests · 3 bedrooms · 2 baths · Vrbo

4.8

(14)

$225

Entire cabin

4 Bedroom House in the Berkshires. Minutes from Tanglewood.

9 guests · 4 bedrooms · 3 baths · Vrbo

5.0

(10)

$850

Entire house

Walk To Town or Hang By The Pool

8 guests · 4 bedrooms · 3 baths · Vrbo

5.0

(10)

$1,000

Entire house

Modern Victorian Walk to Town

8 guests · 4 bedrooms · 3 baths · Vrbo

5.0

(9)

$400

Entire house

Renovated house on the Hill. Walk everywhere!

10 guests · 4 bedrooms · 3 baths · Vrbo

4.4

(11)

$471

Search by amenity

Explore vacation rentals with the most popular amenities in Great Barrington

Kitchen / Kitchenette

Search by location

Looking for a vacation rental near a particular attraction, famous landmark, or another point of interest? Use this map of Great Barrington to help guide your rental search.

Show rentals on map

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.