The Berkshires Vacation Rentals

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Browse Select The Berkshires Vacation Homes

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Exterior
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
10.0 out of 10, Exceptional, (63)
"It was an amazing stay. The host was very proactive and helpful. "
The price is CA $366
CA $743 total
includes taxes & fees
Nov 24 - Nov 25
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
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.
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
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
Golf
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
10.0 out of 10, Exceptional, (105)
"We really enjoyed our stay at Julie’s home. We will definitely to look to stay here again the next time we visit the area. Highly recommended! "
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
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
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
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
4BR Home w/ Yard & BBQ, 5 min walk to downtown Lee
Outdoor dining
4BR Home w/ Yard & BBQ, 5 min walk to downtown Lee
9.6 out of 10, Exceptional, (5)
"This house had everything one could need for a quick getaway or longer stay. It was very comfortable and situated conveniently to Lee, Lenox and Stockbridge. We spent 3 days exploring and found many things to do. I expect to return and we would rent this house again in a heartbeat."
4BR Home w/ Yard & BBQ, 5 min walk to downtown Lee
Berkshires sanctuary w/ outdoor living area & fire pit. Minutes from Tanglewood!
Property grounds
Berkshires sanctuary w/ outdoor living area & fire pit. Minutes from Tanglewood!
10.0 out of 10, Exceptional, (2)
"Delightful property, worked well for our needs"
Berkshires sanctuary w/ outdoor living area & fire pit. Minutes from Tanglewood!
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
Cheerful 3-bedroom cottage with woodstove
Property grounds
Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (30)
"Delightful home in very quiet neighborhood near hiking trails. House had every amenity you might need (except tissues). Less than 20 minutes drive from Sheffield. Great restaurants in town. We very much enjoyed our stay in this house in the country and would highly recommend it to anyone wanting to stay in the area."
The price is CA $331
CA $708 total
includes taxes & fees
Nov 24 - Nov 25
Cheerful 3-bedroom cottage with woodstove
Wellspring by AvantStay | Indoor Pool + Views
Exterior
Wellspring by AvantStay | Indoor Pool + Views
10.0 out of 10, Exceptional, (8)
"The location is absolutely beautiful, the pool was great, and there was plenty of room for everyone. This was our second time staying at this house and we will be back."
Wellspring by AvantStay | Indoor Pool + Views
Find your Sanctuary at The Rectory at Stockbridge
Dining
Find your Sanctuary at The Rectory at Stockbridge
10.0 out of 10, Exceptional, (6)
"The host, Samantha, was ideal! She was communicative, accomodating, and attentive. The place was perfect, right in the heart of town"
The price is CA $908
CA $1,498 total
includes taxes & fees
Nov 24 - Nov 25
Find your Sanctuary at The Rectory at Stockbridge
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Terrace/patio
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
9.2 out of 10, Wonderful, (5)
"The property was spacious and inviting for all of us. The location was perfect. The property manager was very open to suggestions for making some small improvements. "
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Hancock Village Inn at Jiminy Peak
Miscellaneous
Hancock Village Inn at Jiminy Peak
9.8 out of 10, Exceptional, (8)
"We loved this large, well-kept home. The house has tons of room, so even though we had a large group, everyone found space and we never felt crowded. The kitchen/dining area is a great space for gathering and sharing a meal. And, the younger members of our group loved the hot tub and large yard for playing in. The owner was extremely easy to communicate with. We hope to be back!"
The price is CA $905
CA $1,549 total
includes taxes & fees
Nov 25 - Nov 26
Hancock Village Inn at Jiminy Peak
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 The Berkshires

Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1746)
"The pool/clubhouse was a bit chaotic but the overall experience of this location was fantastic. It was lovely."
The price is CA $236
CA $273 total
includes taxes & fees
Nov 26 - Nov 27
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is CA $208
CA $228 total
includes taxes & fees
Nov 25 - Nov 26
Jiminy Peak Mountain Resort
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
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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