Great Barrington Vacation Rentals

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Browse Select Great Barrington Vacation Homes

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Exterior

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

9.6 out of 10, Exceptional, (18)
"Very nice, as expected! "
The price is CA $264
CA $515 total
includes taxes & fees
Nov 24 - Nov 25
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Amore Estate - beautiful room with many places to explore and relax in.
Fridge, microwave, oven, stovetop

Amore Estate - beautiful room with many places to explore and relax in.

9.8 out of 10, Exceptional, (17)
"Beautiful, spacious house in a great location!"
Amore Estate - beautiful room with many places to explore and relax in.
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
Property grounds

Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

10.0 out of 10, Exceptional, (49)
"We had such a great time at this house with our family. We were able to check in early and the place was clean and packed full of supplies for us to use during our stay such as plates, napkins, shampoo/conditioner, hair dryer, coffee, etc.! We brought fishing rods and fished off the dock. We also used the kayaks to go out on the lake and it was so much fun! Anytime we messaged Michael and Beverly they responded within minutes! We were able to check out late and it was the easiest check out I’ve...
The price is CA $419
CA $715 total
includes taxes & fees
Dec 4 - Dec 5
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
Secluded Family Home in Serene Stockbridge Woods
Fridge, microwave, oven, stovetop

Secluded Family Home in Serene Stockbridge Woods

10.0 out of 10, Exceptional, (18)
"We spent a short weekend here in Stockbridge to attend the Naumkeag Pumpkin Show. The kids (2 + 4) were in amazement the entire time. The house was a fantastically creative environment with books, games, toys, and a massive yard with swings. A+ would stay again."
Secluded Family Home in Serene Stockbridge Woods
Spectacular views and close to Great Barrington.
Smart TV, fireplace

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (225)
"One of the best properties i've ever stayed at "
The price is CA $200
CA $309 total
includes taxes & fees
Nov 25 - Nov 26
Berkshire Village Carriage House - Super Private!!
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Dining

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

10.0 out of 10, Exceptional, (116)
"As with our previous several stays, we thoroughly enjoyed the comfort and location of the house. We had a great time and can’t wait to do it all over again next Summer. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!
Beach

Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!

10.0 out of 10, Exceptional, (90)
"Beautiful spot on the lake. Great house. "
Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Exterior

4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

10.0 out of 10, Exceptional, (146)
"Beautiful fall colors surrounding the lake. "
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Tranquil 3-BR Waterfront Retreat
Exterior

Tranquil 3-BR Waterfront Retreat

9.8 out of 10, Exceptional, (10)
"Very clean and nicely decorated. Comfortable vibe. Came to relax and enjoy the fall colors. It looks bigger in the pictures, but was plenty big for the 4 of us. Having laundry was a plus, and enjoyed the ping pong table Loved the duvet covers…so soft. Upstairs bathroom could use a mirror in a better place, as blow drying hair and putting on makeup would be difficult, but just didn’t bother. Hope to go again next fall. "
Tranquil 3-BR Waterfront Retreat
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
Fridge, microwave, oven, stovetop

Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!

10.0 out of 10, Exceptional, (134)
"Everything about this property makes it a wonderful get-away … gorgeous woodland and trails on property, quiet and remote but with all the comforts of a spacious home. The barn renovation is perfect - the right balance of original charm and modern amenities. The hot tub and sauna, and outdoor fire pit, made it a 100% fun and relaxing weekend for my family. This property truly is a slice of paradise! "
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Interior

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.4 out of 10, Exceptional, (36)
"Fun girl’s weekend in the Berkshires! We will be back! Loved the rental and had lots of space! Beds were comfy and we had a great time. "
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow
Fridge, microwave, oven, stovetop

Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow

10.0 out of 10, Exceptional, (90)
"Very clean, spacious, and comfortable. Property manager’s information was helpful."
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow
Family House On Highland Lake with Dock
Fridge, microwave, oven, stovetop

Family House On Highland Lake with Dock

10.0 out of 10, Exceptional, (23)
"Stayed for labor day with family from out of state. Plenty of room for 4 adults and 4 kids, Could have easily fit more. Had a great time on the dock and having fires in the back yard. "
Family House On Highland Lake with Dock
Modern-Chic Athens Home - Fish, Ski & Swim!
Fridge, microwave, stovetop, coffee/tea maker

Modern-Chic Athens Home - Fish, Ski & Swim!

9.8 out of 10, Exceptional, (15)
"Nice host and home! The owner was very responsive when i pointed out a minor issue in the bathroom. We took off one star because, as a group, we felt the cleaning fee was too high, especially considering you are required to clean before you leave."
Modern-Chic Athens Home - Fish, Ski & Swim!
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Fridge, microwave, oven, stovetop

NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

10.0 out of 10, Exceptional, (31)
"The castle house is fantastic. Spacious, beautifully decorated and equipped. There is no meal you can't craft from this kitchen. The house is super quiet,the beds are comfy, towels plush...close to Great Barrington. I can't say enough good things. Book it."
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Cozy log cabin in Lake Community.
Terrace/patio

Cozy log cabin in Lake Community.

10.0 out of 10, Exceptional, (18)
"It was quiet, cozy, spacious and clean!! So very inviting and we did not want to leave!!"
Cozy log cabin in Lake Community.
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond
Property grounds

Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond

10.0 out of 10, Exceptional, (33)
"We had a wonderful time at this property! It was perfect for what we wanted- a place to ourselves in nature with beautiful views. Host was great! Would definitely recommend! "
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond
Bluebird Valley Farmhouse
Beach

Bluebird Valley Farmhouse

10.0 out of 10, Exceptional, (59)
"If ever in the area again, we will definitely stay at Bluebird Farmhouse. It is so charming with wonderful artwork throughout this warm and comfortable home. A beautiful setting with a very well equipped home providing everything you need. We were in town for a wedding and thoroughly enjoyed our stay at this special farmhouse!!"
Bluebird Valley Farmhouse
Mountain View Getaway
Outdoor dining

Mountain View Getaway

10.0 out of 10, Exceptional, (45)
"My daughter, granddaughter and I spent a wonderful weekend at this home. We enjoyed every second of the view, wildlife, peacefulness, and each other. We built puzzles, cooked wonderful meals, and relaxed. Beautiful home, perfectly kept, fun amenities, and wonderful hosts! We highly recommend."
Mountain View Getaway
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.
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Other property types in Great Barrington

The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Interior

The Freeman - Newly Renovated 14K SF Estate on 40 Acres

10.0 out of 10, Exceptional, (31)
"We loved the Freeman estate for our wedding!! Daniel and Anna were super helpful and the property was amazing! The house had so many amenities it was beyond our expectations. Our guests were astounded by the home and the surrounding property, would HIGHLY recommend to anyone and everyone. "
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Private Estate, Heated YEARROUND Outdoor Pool
Fridge, microwave, oven, stovetop

Private Estate, Heated YEARROUND Outdoor Pool

10.0 out of 10, Exceptional, (13)
"The country setting provided a quiet retreat. The home is well equipped: plenty of beds, multiple gathering places, pool with towels (although it was pretty cold until the pool guy came and provided help). The outdoor grill provides additional cooking space. The home is within easy driving to many places of interest. We had a nice week at this home."
Private Estate, Heated YEARROUND Outdoor Pool
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
TV, fireplace, DVD player, books

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (41)
"We had expectations of a peaceful rustic cabin in the woods, and this rental checked almost all of the boxes! The quaint town of Great Barrington was just close enough for convenience, but the house was rural enough to help us all relax and enjoy the quiet. We loved the dock and the firepit, and the house was well-stocked with firewood, towels, and toiletries. "
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
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.
Beautiful view of the beach with palm trees

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