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Holiday homes in Great Barrington You’ll Love

Top-Rated Great Barrington Holiday homes for Every Budget and Style!

Looking for a holiday home in Great Barrington (Massachusetts)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $51.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Great Barrington.

We found 17 Holiday-homes in Great Barrington and the surrounding area (within 30 miles)

The Freeman- 14K SF Estate 40acrs Tennis Vineyard in Sheffield, USA

The Freeman- 14K SF Estate 40acrs Tennis...

Villa in Sheffield near Great Barrington, Massachusetts , 1379 Bow Wow Road
Featuring water sports facilities, The Freeman- 14K SF Estate 40acrs Tennis Vineyard provides accommodations in Sheffield.
  • Parking
  • Pets allowed
  • Family rooms
  • Kids' outdoor play equipment

Exceptional 1 Reviews 10.0

from $82.00 Show details »

Skiing and Hiking Water-View Home in the Berkshires in Sheffield, USA

Skiing and Hiking Water-View Home in the...

Holiday home in Sheffield near Great Barrington, Massachusetts
Skiing and Hiking Water-View Home in the Berkshires is located in Sheffield, just 19 miles from Cranwell Spa & Golf Club and 20 miles from Tanglewood ...
  • Parking

Fabulous 3 Reviews 9.0

from $343.72 Show details »

Whitney by AvantStay Private Berkshires Estate in Sheffield, USA

Whitney by AvantStay Private Berkshires...

Holiday home in Sheffield near Great Barrington, Massachusetts
Whitney by AvantStay Private Berkshires Estate is located in Sheffield, just 18 miles from Tanglewood Musical Center and 19 miles from Tanglewood.
  • Parking
  • Pets allowed

no reviews

from $233.53 Show details »

Berkshire Vacation Rentals: Peaceful Post and Beam Loft Sleeps 9 in New Marlborough, USA

Berkshire Vacation Rentals: Peaceful Pos...

Holiday home in New Marlborough near Great Barrington, Massachusetts , Hartsville Mill River Road 1089
Berkshire Vacation Rentals: Peaceful Post and Beam Loft Sleeps 9 offers accommodations in New Marlborough, 15 miles from Norman Rockwell Museum and 17...
  • Parking
  • Pets allowed

Exceptional 2 Reviews 9.5

from $261.02 Show details »

Half Moon by AvantStay 4BR Cabin w Large Deck Yard w Patio Outdoor Dining in Great Barrington, USA

Half Moon by AvantStay 4BR Cabin w Large...

Holiday home in Great Barrington, Massachusetts
Half Moon by AvantStay 4BR Cabin w Large Deck Yard w Patio Outdoor Dining offers accommodations in Great Barrington, 11 miles from Norman Rockwell Mus...
  • Pets allowed

Good 1 Reviews 7.0

from $299.28 Show details »

Cozy Great Barrington Home about 1 Mi to Ski Resort! in Great Barrington, USA

Cozy Great Barrington Home about 1 Mi to...

Holiday home in Great Barrington, Massachusetts
Cozy Great Barrington Home about 1 Mi to Ski Resort! is located in Great Barrington, just 14 miles from Cranwell Spa & Golf Club and 14 miles from Tan...
  • Parking

Good 1 Reviews 7.0

from $487.09 Show details »

Berkshire Vacation Rentals: Great Barrington Walkable To Lake And Town in Great Barrington, USA

Berkshire Vacation Rentals: Great Barrin...

Holiday home in Great Barrington, Massachusetts , Lake Avenue 16
Berkshire Vacation Rentals: Great Barrington Walkable To Lake And Town is located in Great Barrington, just 14 miles from Cranwell Spa & Golf Club and...
  • Parking
  • Pets allowed

No reviews yet 1 Reviews 1.0

from $436.37 Show details »

Linden by AvantStay Countryside Berkshire Escape in North Egremont, USA

Linden by AvantStay Countryside Berkshir...

Holiday home in North Egremont near Great Barrington, Massachusetts
Linden by AvantStay Countryside Berkshire Escape is located in North Egremont, just 11 miles from Norman Rockwell Museum and 16 miles from Tanglewood ...
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $57.00 Show details »

Magical Country Retreat in the Berkshires in Great Barrington, USA

Magical Country Retreat in the Berkshire...

Holiday home in Great Barrington, Massachusetts , 250 Long Pond Road
Providing a garden, Magical Country Retreat in the Berkshires offers accommodations in Great Barrington.
  • Parking
  • Bar
  • Family rooms
  • Outdoor pool
  • Swimming Pool

no reviews

from $4.626.94 Show details »

Great Barrington Lakeside Getaway with Kayak and Grill in Great Barrington, USA

Great Barrington Lakeside Getaway with K...

Holiday home in Great Barrington, Massachusetts
Great Barrington Lakeside Getaway with Kayak and Grill is located in Great Barrington, just 10 miles from Tanglewood Musical Center and 10 miles from ...
  • Parking

Superb 3 Reviews 9.3

from $388.34 Show details »

Lakefront Berkshires Retreat with Deck, Dock and Boat! in Great Barrington, USA

Lakefront Berkshires Retreat with Deck,...

Holiday home in Great Barrington, Massachusetts
Lakefront Berkshires Retreat with Deck, Dock and Boat! is located in Great Barrington, just 5.2 miles from Norman Rockwell Museum and 10 miles from Ta...
  • Parking
  • Pets allowed

Good 4 Reviews 7.5

from $351.06 Show details »

Woodland Zen by AvantStay Modern Design Patio in Stockbridge, USA

Woodland Zen by AvantStay Modern Design...

Holiday home in Stockbridge near Great Barrington, Massachusetts
Woodland Zen by AvantStay Modern Design Patio is located in Stockbridge, just 3.2 miles from Norman Rockwell Museum and 7.7 miles from Tanglewood Musi...
  • Parking

no reviews

from $346.65 Show details »

Berkshire Vacation Rentals: Spacious & Serene Berkshires Retreat In The Woods in West Stockbridge, USA

Berkshire Vacation Rentals: Spacious & S...

Holiday home in West Stockbridge near Great Barrington, Massachusetts , Robin Road 4
Berkshire Vacation Rentals: Spacious & Serene Berkshires Retreat In The Woods offers accommodations in West Stockbridge, 3.2 miles from Norman Rockwel...
  • Parking
  • Pets allowed

no reviews

from $82.00 Show details »

Berkshire Vacation Rental: Stockbridge Home Come Experience The Berkshires in Stockbridge, USA

Berkshire Vacation Rental: Stockbridge H...

Holiday home in Stockbridge near Great Barrington, Massachusetts , Goodrich Street 22
Berkshire Vacation Rental: Stockbridge Home Come Experience The Berkshires offers accommodations in Stockbridge, 3.7 miles from Norman Rockwell Museum...
  • Parking
  • Pets allowed

Exceptional 3 Reviews 10.0

from $462.25 Show details »

Stockbridge Retreat with Pool and Hot Tub! in Stockbridge, USA

Stockbridge Retreat with Pool and Hot Tu...

Holiday home in Stockbridge near Great Barrington, Massachusetts
Stockbridge Retreat with Pool and Hot Tub! is located in Stockbridge, just 3.8 miles from Norman Rockwell Museum and 6.8 miles from Cranwell Spa & Gol...
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $1.677.89 Show details »

Too Good AKA 2 Goodrich St in Stockbridge, USA

Too Good AKA 2 Goodrich St

Holiday home in Stockbridge near Great Barrington, Massachusetts , 2 Goodrich Street
Too Good AKA 2 Goodrich St offers accommodations in Stockbridge, 6.9 miles from Tanglewood and 19 miles from Great Falls.
  • Family rooms

Exceptional 2 Reviews 10.0

from $403.19 Show details »

Classic Stockbridge Cottage in Stockbridge, USA

Classic Stockbridge Cottage

Holiday home in Stockbridge near Great Barrington, Massachusetts , Christian Hill Road 15
Classic Stockbridge Cottage is located in Stockbridge, just a 19-minute walk from Norman Rockwell Museum and 5.6 miles from Tanglewood Musical Center.
  • Parking
  • Pets allowed

no reviews

from $473.45 Show details »

Number of Holiday homes in Great Barrington 17
Number of guest ratings 1,720
Average price per night $369.00
Lowest price per night $51,00
Highest price per night $4.626,94

Top 10 Cheapest Holiday-homes in Great Barrington

Discover the Cheapest Holiday-homes in Great Barrington – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Holiday-homes in Great Barrington

Check out the Most Booked Holiday-homes in Great Barrington – Based on Guest Popularity.

Holiday homes in Great Barrington (Massachusetts), comfortable and familiar

Staying in a holiday or vacation home in Great Barrington can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Great Barrington for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Great Barrington should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com