Showing

PreviousNext property

$250

3 BR / 2 BA / Sleeps 8

Maya's Garden House - Great Barrington vacation rentals
1 / 19

$250

Inquire

Maya's Garden House

3 BR / 2 BA / Sleeps 8 | Quick view

Details

Surrounded by one of the most beautiful gardens in the Berkshires, Maya's Garden House is an outstanding example of an 18th century barn converted into a modern, comfortable, semi-secluded home. Located less than a mile from Great Barrington, it is close to everything the Berkshires are famous for; Tanglewood, Jacob's…
  • Mountain Views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly

PreviousNext property

$650

4 BR / 6 BA / Sleeps 12

Country Elegance in the Berkshires - Great Barrington vacation rentals
1 / 22

$650

Book

Country Elegance in the Berkshires

4 BR / 6 BA / Sleeps 12 | Quick view

Details

This immaculate home is the place for relaxing, entertaining and sharing great times with family and friends. The house sets over 4 beautifully wooded acres. We call it the "illision of seclusion," as it is very private and yet is 5 minutes from the town as well as lakes, hiking, movies, theater, shops, …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

PreviousNext property

$357

5 BR / 5 BA / Sleeps 12

Elegant 6000+Sf Luxury Estate on 13+ Park - Great Barrington vacation rentals
1 / 23

$357

Inquire

Elegant 6000+Sf Luxury Estate on 13+ Park

5 BR / 5 BA / Sleeps 12 | Quick view

Details

This Elegant Luxury Estate offers 6000+ SF of Living Space on 13+ park-like, sunny acres located within only minutes from the downtown Great Barrington. This fantastic home offers 5 Bedrooms, 4.5 bathrooms, sweeping dual staircase ending with the magnificent open gallery, the kitchen offers the magnificent, high end …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Suitable for children - ask
  • Suitable for the elderly - ask

PreviousNext property

$200

4 BR / 3 BA / Sleeps 10

Cosy family house with a swimming pool - Great Barrington vacation rentals
1 / 13

$200

Book

Cosy family house with a swimming pool

4 BR / 3 BA / Sleeps 10 | Quick view

Details

Sweet cozy house with plenty of room for large groups coming to enjoy the treasures of the Berkshires. Nestled behind Monument Mountain in Great Barrington. 4 bedrooms, 2.5 bathrooms, a spacious kitchen, living room, TV room, game room with pool/Ping-Pong table & two cars garage. Located within a neighborhood friendly…
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - ask

PreviousNext property

$300

3 BR / 2 BA / Sleeps 6

Sunroom comfort, spread-out room for everyone - Great Barrington vacation rentals
1 / 23

$300

Book

Sunroom comfort, spread-out room for everyone

3 BR / 2 BA / Sleeps 6 | Quick view

Details

Beautifully furnished, updated 3,000 square foot house. 3 bedrooms, 2 full baths; large sun room with great windows and sky-lights, comfortable seating area for 6 plus cafe table; dining room with table for 6 to 8 people; reading room with a wood-burning stove; living room with a fireplace; private fence-enclosed …
  • Mountain Views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly

PreviousNext property

$350

5 BR / 3 BA / Sleeps 10

Berkshire Lakefront House - Great Barrington vacation rentals
1 / 9

$350

Book

Berkshire Lakefront House

5 BR / 3 BA / Sleeps 10 | Quick view

Details

Attractive year-round lakefront house in a wooded area on a pristine Round Pond in the Berkshires. Relax and enjoy the view from your deck or dock. Fish from the dock or take the boat out onto the lake. Ideal family retreat in Great Barrington and only a short drive to cultural attractions (Tanglewood, Rockwell Museum…
  • Waterfront
  • Ocean or water views
  • Mountain Views
  • Internet Access
  • Fireplace
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$465

4 BR / 4 BA / Sleeps 12

3 Reviews

$465

Book

Gem of the Berkshires, walk to downtown & lake.

4 BR / 4 BA / Sleeps 12 | Quick view
“ Excellent ” 3 Reviews

Details

Reviews

(3)

This sparkling, newly renovated cottage is for available vacation rental. A stunning sunrise & gorgeous view of the Berkshire Mountains. Conveniently located near many attractions. The house has been renovated by a contemporary designer. It has an open floor plan, making each room flow into another. The main …
  • Mountain Views
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(3)

beautiful review and wonderful owners.

Left on Jul 03, 2012 for a stay in June 2012

We stayed here for a weekend with friends and couldn't have asked for a better time. The house is located on a hill above Great Barrington and has access to a lake. Ephrat is perhaps the nicest owner I've ever worked with on a vacation rental. She treated us like guests, not renters, and took the time to give us a wonderful tour of the beautiful property. The next morning she even dropped off…

PreviousNext property

$350

4 BR / 2 BA / Sleeps 9

1 Reviews

$350

Book

Field View Cottage , Convenient to All Berkshire

4 BR / 2 BA / Sleeps 9 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

The perfect house for friends and family to share! Bright,uncluttered, and inviting, with privacy and views just minutes to town. There are two fireplaces,a sunken living room, dining room with seating for 10, 4 bedrooms, 2 full bathrooms, and a cozy hang out area in the basement. There is a washer and dryer, …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Best Memorable Thanksgiving Ever

Left on Feb 05, 2015 for a stay in November 2014

This was the first time we had a rental cottage, but it surpassed all of our expectations. The cottage was clean and well arranged. Kitchen was spacious enough for more than a few people cook together. Fireplace was lovely and so fun! The neighborhood was so quiet and calm. It snowed right before Thanksgiving, and the view was priceless! We would like to come back again!

PreviousNext property

$350

5 BR / 4 BA / Sleeps 10

2 Reviews

$350

Book

Shaker Hill

5 BR / 4 BA / Sleeps 10 | Quick view
“ Very Good ” 2 Reviews

Details

Reviews

(2)

Shaker Hill is a quirky rambling farmhouse located less than 3 hours from NYC and Boston. Hidden away down a 400’ unpaved driveway on 30 acres of fields and forest in the heart of the Berkshires, Shaker Hill is totally private and surrounded by 30 acres of rolling fields, diverse wetlands, wildlife and forest. It…
  • Mountain Views
  • Internet Access
  • Outdoor Dining Area
  • A/C or climate control
  • Central heating
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(2)

Big house, private, but a few drawbacks

Left on Sep 11, 2014 for a stay in August 2014

This is a very large house, more than adequate in size for a group of ten people. It has a big yard and a spectacular view of the mountains, especially from an upstairs window. The playroom is a nice touch for those with kids. There are two staircases, which is also nice.

I was under the impression that there were four full bathrooms (which I took to mean with showers). When we arrived, we…

PreviousNext property

$172

3 BR / 2 BA / Sleeps 6

1 / 16

$172

Book

Charming get-a-way in Great Barrington Berkshires

3 BR / 2 BA / Sleeps 6 | Quick view

Details

Charming get-a-way in a friendly residential neighborhood in Great Barrington. Our home is sunny and bright, with an eat-in-kitchen, casual living room and dining area with beautiful picture windows, three comfortable bedrooms, and 1.5 bathrooms. Fully furnished with an eclectic mix of modern and older finds from the …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly - ask
  • Suitable for children

PreviousNext property

$243

2 BR / 2 BA / Sleeps 4

1 Reviews

$243

Book

Cozy and clean in Gt Barrington- 1 week in summer!

2 BR / 2 BA / Sleeps 4 | Quick view
“ Very Good ” 1 Reviews

Details

Reviews

(1)

Our home is located in Great Barrington, given the title of the #1 Best Small Town in America by Smithsonian Magazine. There are many great restaurants, shopping, the Mahaiwe theater, a cineplex, golf, natural foods Co-op, a State Forest, yoga studio, and more. There are about twelve (12!) hiking trails in Great …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Porch
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(1)

Easy, comfortable summer getaway!

Left on Feb 02, 2015 for a stay in August 2013

My cousin and I thoroughly enjoyed our stay. The house was cozy and very convenient for our needs. Having a laundry room just off the kitchen was great when we came back from the lake, the bedrooms were airy with cross ventilation and the screened in porch was a great place to linger over coffee in the morning. The location is also wonderful! It is only a 5 minute drive to lake Mansfield, 7or 8 …

PreviousNext property

$250

2 BR / 1 BA / Sleeps 5

2 Reviews

$250

Book

1940's Cabin with fantastic 180o mountain views!!

2 BR / 1 BA / Sleeps 5 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

Please note that this property is not winterized so it's not available this winter of 2012. I am winterizing this spring & the property will be available on a year around basis stating on 5/15/2013. Please go to (website: hidden) listing #219964 to see my reviews, I am new to flipkey. Located in South Egremont, 3 …
  • Mountain Views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly

Details

Reviews

(2)

What a wonderful cabin! What an amazing location! - The perfect log cabin getaway

Left on May 20, 2013 for a stay in May 2013

This was a perfect weekend for us. I am very picking when choosing a cabin rental because I want it to be "just right--" to fit into all of my ideal visions of the quintessential cozy cabin. Jonathan's Luka Lodge has it-- you feel totally isolated and yet you're only minutes away from delicious restaurants and gourmet shopping. The furnishings and decor are subdued and add to the rustic but …

PreviousNext property

$200

2 BR / 1 BA / Sleeps 4

1 / 10

$200

Book

Berkshire Schoolhouse Cottage

2 BR / 1 BA / Sleeps 4 | Quick view

Details

Welcome to our School House Cottage located in the heart of the Berkshires. Set in front of the ledges of Warner Mountain, this historic home was originally a three room schoolhouse. An addition in the 1960's transformed it into a private home which it remained for many years. Now updated, the cottage has become a …
  • Internet Access
  • Housekeeping Optional
  • A/C or climate control
  • Parking
  • Books
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

PreviousNext property

$225

1 BR / 1 BA / Sleeps 3

12 Reviews

$225

Book

Berkshires: Romantic Cottage with spectacular view

1 BR / 1 BA / Sleeps 3 | Quick view
“ Excellent ” 12 Reviews

Details

Reviews

(12)

Berkshires: Romantic Berkshires Cottage with Stunning Views (Great Barrington) The Berkshires in spring, summer and fall are alive with beauty, and now is the time to plan your restoring getaway in this idyllic studio cottage with its glorious views of the rolling hills and verdant meadows.. Nature lovers, artists…
  • Mountain Views
  • Shared outdoor pool (unheated)
  • Internet Access
  • Central heating
  • Parking
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly

Details

Reviews

(12)

Peaceful and relaxing weekend

Left on Sep 06, 2011 for a stay in August 2011

My husband and I stayed here while visiting Great Barrington for the weekend. The space is immaculate and very quaintly designed. There is ample space to spread out. Bed is comfortable, full bath is very clean and towels are provided. No stovetop, but a full fridge and kitchen sink. Not much need for a kitchen since downtown is just minutes away and offers plenty of excellent restaurants. The …

PreviousNext property

$230

1 BR / 1 BA / Sleeps 2

1 / 16

$230

Book

Cill Aodain Cabin

1 BR / 1 BA / Sleeps 2 | Quick view

Details

One bedroom, one bathroom cottage on beautiful country road. Private garden and screened-in porch. Two miles to shops and restaurants of downtown Great Barrington. Enjoy nearby skiing, cycling, fishing, hiking and golf. The Space: Quaint cottage with wood burning stove. Ideal base for enjoying the best of the …
  • Mountain Views
  • Internet Access
  • Fireplace
  • Deck
  • Parking
  • Pet friendly
  • Suitable for children - ask

PreviousNext property

$188

4 BR / 2 BA / Sleeps 10

1 / 12

$188

Inquire

Lakefront Berkshires Ski/Summer House, Great Views

4 BR / 2 BA / Sleeps 10 | Quick view

Details

Located in a wooded area overlooking a pristine lake, this woodsy style contemporary is a sportsman's paradise. It's a short drive to skiing (Jiminy Peak, Butternut, Catamount) and cultural attractions, (Tanglewood, National Music Center, Aston Magna, etc.) or you can fish, swim, boat, hike, or lounge on the deck and …
  • Waterfront
  • Ocean or water views
  • Mountain Views
  • Internet Access
  • Fireplace
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

PreviousNext property

$643

6 BR / 6 BA / Sleeps 12

1 / 25

$643

Book

Berkshire Estate: Exquisitely furnished 7,000sf

6 BR / 6 BA / Sleeps 12 | Quick view

Details

This home is uniquely and magnificently furnished by a retired couple that spent 18 years traveling and living abroad. Even local real estate agents have called the house “special”. It has 7,000 sf of living space (3 floors) with plenty of places to be together or to be alone (as one so chooses). It is on 9 …
  • Mountain Views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children - ask
  • Suitable for the elderly - ask

Looking for more rentals?


We're showing only results that match your dates and preferences.


See all 17 Great Barrington rentals, all 111 Berkshires rentals, or start a new search.


There are no more results in Great Barrington. Top of page