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Holiday homes in Great Barrington

Enjoy your stay and find the best Holiday homes in Great Barrington at affordable prices

Searching for a holiday home in Great Barrington (Massachusetts)? Explore a great selection of vacation homes in Great Barrington to find the one that best fits to your needs, starting from $123 per night. Holiday homes offer a relaxing escape, providing a cozy retreat for vacationers seeking a home away from home.

Holiday-homes in Great Barrington and region (30 miles)
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
Located in Great Barrington, 18 km from Norman Rockwell Museum, 22 km from Cranwell Spa & Golf Club and 23 km from Tanglewood Musical Center, Cozy Gre...
  • Parking

Very good 2 Reviews 8.5

from $488.67 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
Offering lake views, Lakefront Berkshires Retreat with Deck, Dock and Boat! is an accommodation set in Great Barrington, 8.3 km from Norman Rockwell M...
  • Parking
  • Pets allowed
  • Internet facilities
  • Hairdryer
  • Iron

Good 4 Reviews 7.7

from $329.00 Show details »

Waterfront Cottage 10 Min to Great Barrington! in New Marlborough, USA

Waterfront Cottage 10 Min to Great Barri...

Holiday home in New Marlborough near Great Barrington, Massachusetts
Waterfront Lake Buel Cottage 7 Mi to Monument Mtn is located in New Marlborough, 25 km from Cranwell Spa & Golf Club, 26 km from Tanglewood Musical Ce...
  • Parking
  • Internet facilities
  • Refrigerator
  • DVD player
  • Fan

Exceptional 1 Reviews 10.0

from $465.00 Show details »

Rustic Berkshires Cottage at Lake Buel with Kayaks! in New Marlborough, USA

Rustic Berkshires Cottage at Lake Buel w...

Holiday home in New Marlborough near Great Barrington, Massachusetts
Situated in New Marlborough, 21 km from Norman Rockwell Museum, 25 km from Cranwell Spa & Golf Club and 26 km from Tanglewood Musical Center, Rustic B...
  • Parking
  • Pets allowed

Superb 4 Reviews 9.3

from $262.67 Show details »

Waterview Home in the Berkshires Near Hiking in Sheffield, USA

Waterview Home in the Berkshires Near Hi...

Holiday home in Sheffield near Great Barrington, Massachusetts
Set 25 km from Norman Rockwell Museum, 31 km from Cranwell Spa & Golf Club and 32 km from Tanglewood Musical Center, Waterfront Sheffield Escape with ...
  • Parking

no reviews

from $340.67 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
Within 5.1 km of Norman Rockwell Museum and 10 km of Cranwell Spa & Golf Club, Too Good AKA 2 Goodrich St offers free WiFi and a garden.
  • Family rooms

no reviews

from $449.00 Show details »

Tranquil 3 BR Stockbridge House with Private Deck! in Stockbridge, USA

Tranquil 3 BR Stockbridge House with Pri...

Holiday home in Stockbridge near Great Barrington, Massachusetts
Tranquil 3BR Stockbridge House with Private Deck! is situated in Stockbridge, 8.5 km from Tanglewood Musical Center, 9.1 km from Tanglewood, and 14 km...
  • Parking
  • Pets allowed
  • Internet facilities
  • Hairdryer
  • Iron

Superb 2 Reviews 9.5

from $416.00 Show details »

The Mill River Cabin with Fireplace and River View! in Mill River, USA

The Mill River Cabin with Fireplace and...

Holiday home in Mill River near Great Barrington, Massachusetts
The Mill River Cabin with Fireplace and River View! is situated in Mill River, 30 km from Norman Rockwell Museum, 35 km from Cranwell Spa & Golf Club,...
  • Parking
  • Pets allowed
  • Internet facilities
  • Hairdryer
  • Toilet

Superb 4 Reviews 9.5

from $244.33 Show details »

Cozy Monterey Home with Porch Walk to Lake Garfield in Monterey, USA

Cozy Monterey Home with Porch Walk to La...

Holiday home in Monterey near Great Barrington, Massachusetts
Set 22 km from Norman Rockwell Museum, 24 km from Tanglewood and 25 km from Tanglewood Musical Center, Cozy Monterey Home with Porch Walk to Lake Garf...
  • Parking

no reviews

from $304.14 Show details »

Cozy Stockbridge Cabin - Walk to Beach and Lake! in Stockbridge, USA

Cozy Stockbridge Cabin - Walk to Beach a...

Holiday home in Stockbridge near Great Barrington, Massachusetts
Set in Stockbridge, 4.7 km from Tanglewood Musical Center and 5.1 km from Norman Rockwell Museum, Cozy Stockbridge Cabin - Walk to Beach and Lake! pro...
  • Parking

Superb 2 Reviews 9.5

from $341.00 Show details »

Stockbridge Home Walk to Town Beach! in Stockbridge, USA

Stockbridge Home Walk to Town Beach!

Holiday home in Stockbridge near Great Barrington, Massachusetts
Stockbridge Home - Walk to Lakefront Beach! is situated in Stockbridge, 3.9 km from Tanglewood, 5.7 km from Cranwell Spa & Golf Club, and 6.5 km from ...
  • Parking

no reviews

from $272.33 Show details »

Beautiful Lakehouse with POOL TABLE by CozySuites in Copake, USA

Beautiful Lakehouse with POOL TABLE by C...

Holiday home in Copake near Great Barrington, Massachusetts
Set in Copake, 39 km from Norman Rockwell Museum, 46 km from Cranwell Spa & Golf Club and 46 km from Tanglewood Musical Center, Beautiful Lakehouse wi...
  • Parking
  • Tea/Coffee maker
  • Internet facilities
  • TV
  • Air conditioning

no reviews

from $127.33 Show details »

Modern Lakehouse Retreat by CozySuites in Copake, USA

Modern Lakehouse Retreat by CozySuites

Holiday home in Copake near Great Barrington, Massachusetts
Located in Copake, 40 km from Norman Rockwell Museum, 46 km from Cranwell Spa & Golf Club and 47 km from Tanglewood Musical Center, Modern Lakehouse R...
  • Parking
  • Tea/Coffee maker
  • Bath
  • TV
  • Air conditioning

Fabulous 1 Reviews 9.0

from $199.67 Show details »

TWO Beautiful Lakehouse by CozySuites in Copake, USA

TWO Beautiful Lakehouse by CozySuites

Holiday home in Copake near Great Barrington, Massachusetts
Located in Copake, 40 km from Norman Rockwell Museum and 46 km from Cranwell Spa & Golf Club, TWO Beautiful Lakehouse by CozySuites offers free WiFi a...
  • Parking

no reviews

from $315.00 Show details »

Relaxing 2BR Lakehouse by CozySuites in Copake, USA

Relaxing 2BR Lakehouse by CozySuites

Holiday home in Copake near Great Barrington, Massachusetts
Set in Copake, 40 km from Norman Rockwell Museum, 46 km from Cranwell Spa & Golf Club and 47 km from Tanglewood Musical Center, Relaxing 2BR Lakehouse...
  • Parking
  • Tea/Coffee maker
  • Internet facilities
  • Bath
  • TV

Exceptional 1 Reviews 10.0

from $123.00 Show details »

Cabin with 3 Acres, Tennis Courts By 4 Ski Mtns in Sandisfield, USA

Cabin with 3 Acres, Tennis Courts By 4 S...

Holiday home in Sandisfield near Great Barrington, Massachusetts
Situated in Sandisfield, 25 km from Cranwell Spa & Golf Club, 28 km from Norman Rockwell Museum and 29 km from Tanglewood, Cabin with 3 Acres, Tennis ...
  • Parking
  • Pets allowed
  • Internet facilities
  • Hairdryer
  • Refrigerator

Very good 1 Reviews 8.0

from $393.00 Show details »

Berkshires Cabin 2 Mi to Appalachian Trail! in Otis, USA

Berkshires Cabin 2 Mi to Appalachian Tra...

Holiday home in Otis near Great Barrington, Massachusetts
Berkshires Cabin 2 Mi to Appalachian Trail! is located in Otis, 21 km from Cranwell Spa & Golf Club, 25 km from Tanglewood, as well as 26 km from Tang...
  • Parking

no reviews

from $259.00 Show details »

Restored 1881 Farm House in Lenox, USA

Restored 1881 Farm House

Holiday home in Lenox near Great Barrington, Massachusetts , 76 East Dugway Road
Located in Lenox, 5.2 km from Tanglewood and 5.5 km from Cranwell Spa & Golf Club, Restored 1881 Farm House provides air-conditioned accommodation wit...
  • Pets allowed
  • Family rooms

no reviews

from $399.00 Show details »

Restored 1800s Home Half Mile to Ski Resort! in Otis, USA

Restored 1800s Home Half Mile to Ski Res...

Holiday home in Otis near Great Barrington, Massachusetts
Set 26 km from Cranwell Spa & Golf Club and 30 km from Tanglewood in Otis, Restored 1800s Home Half Mile to Ski Resort! offers accommodation with a ki...
  • Parking

no reviews

from $284.29 Show details »

Beautiful Lenox Home, 3 Mi to Shakespeare and Co! in Lenox, USA

Beautiful Lenox Home, 3 Mi to Shakespear...

Holiday home in Lenox near Great Barrington, Massachusetts
Located in Lenox, 5.6 km from Tanglewood and 5.9 km from Cranwell Spa & Golf Club, Beautiful Lenox Home, 3 Mi to Shakespeare and Co! provides accommod...
  • Parking
  • Internet facilities
  • Shower
  • Bath
  • TV

Superb 3 Reviews 9.0

from $346.67 Show details »

APPLEJAX cabin steps from a u pick orchard in Sandisfield, USA

APPLEJAX cabin steps from a u pick orcha...

Holiday home in Sandisfield near Great Barrington, Massachusetts , 98 New Hartford Road
Log cabin w/stone fireplace near Ski mountains! in Sandisfield features accommodation with free WiFi, 39 km from Tanglewood, 39 km from Norman Rockwel...
  • Parking
  • Pets allowed
  • Family rooms

Fabulous 1 Reviews 9.0

from $220.50 Show details »

Berkshires Home on 11 Acres with Pond and 2 Fire Pits! in Becket, USA

Berkshires Home on 11 Acres with Pond an...

Holiday home in Becket near Great Barrington, Massachusetts
Berkshires Home on 11 Acres with Pond and 2 Fire Pits! is located in Becket, 22 km from Cranwell Spa & Golf Club, and provides a patio, garden, and fr...
  • Parking
  • Internet facilities
  • Hairdryer
  • Iron
  • Refrigerator

no reviews

from $383.00 Show details »

Charming Lenox Home View of October Mountain in Lenox, USA

Charming Lenox Home View of October Moun...

Holiday home in Lenox near Great Barrington, Massachusetts
Located in Lenox, within 8.5 km of Tanglewood and 8.8 km of Cranwell Spa & Golf Club, Charming Lenox Home View of October Mountain offers accommodatio...
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $364.00 Show details »

Berkshire Mountain Lodge in Pittsfield, USA

Berkshire Mountain Lodge

Lodge in Pittsfield near Great Barrington, Massachusetts , 8 Dan Fox Drive
Featuring an indoor swimming pool and a fitness centre, Berkshire Mountain Lodge is located in Pittsfield.
  • Parking
  • Sauna
  • Fitness centre
  • Family rooms
  • Indoor pool

Very good 497 Reviews 8.4

from $191.67 Show details »

East Otis Vacation Rental with Private Deck and BBQ! in East Otis, USA

East Otis Vacation Rental with Private D...

Holiday home in East Otis near Great Barrington, Massachusetts
East Otis Romantic Cottage with Deck and BBQ! is situated in East Otis, 35 km from Cranwell Spa & Golf Club, 39 km from Tanglewood, as well as 39 km f...
  • Parking

Fabulous 1 Reviews 9.0

from $206.00 Show details »

Number of Holiday homes in Great Barrington 38
Number of guest ratings 1813
Average price per night $387.99
Lowest price per night $123.00
Highest price per night $995.00

Most popular Holiday-homes in Great Barrington

The most popular Holiday-homes in Great Barrington based on average guest rating (Top 10).

Cheapest Holiday-homes in Great Barrington

The cheapest Holiday-homes in Great Barrington based on room rate per night (Top 10).

Most booked Holiday-homes in Great Barrington

The most booked Holiday-homes in Great Barrington based on popularity with guests (Top 10).

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