Holiday Homes in The Berkshires

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Featured Holiday Homes in The Berkshires

Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (232)
"A beautiful lodge nestled in the woods surrounded by an abundance of trails to hike. "
The price is AU$371
includes taxes & fees
5 Jan - 6 Jan
Berkshire Village Carriage House - Super Private!!
Antique Farmhouse Totally Restored
Exterior

Antique Farmhouse Totally Restored

10.0 out of 10, Exceptional, (83)
"I'd describe the house as elegantly eclectic. The owner is clearly a collector of interesting items which they arrange in a way that enhance (rather than potentially clutter) the interior. The kitchen and living spaces are open and easy to mingle around. The four bedrooms and three bathrooms easily and comfortably accommodated two couples and two singles. Our stay could not have been better! "
Antique Farmhouse Totally Restored
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.
Peace and quiet on the lake
Interior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (201)
"My family and I really enjoyed our stay at the lake. My kids enjoyed playing outside in the snow. We had such a quality family time playing board games, watching movies and drinking hot cocoa. Justin was such a great host and really helpful when needed. We’re definitely coming back!"
Peace and quiet on the lake
Private Estate, Heated Yearround Outdoor Pool
Fridge, microwave, oven, stovetop

Private Estate, Heated Yearround Outdoor Pool

10.0 out of 10, Exceptional, (14)
"Beautiful property, well-appointed, and comfortable for extended family of 12."
Private Estate, Heated Yearround Outdoor Pool
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Interior

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.4 out of 10, Exceptional, (38)
"The home was convenient to hiking, shopping and dining. It is on a busy street and can be a bit tricky getting in and out of driveway. Inside the home was warm and welcoming. The kitchen had all cooking pans and tools we needed to make meals. There is a great grocery store right down the road. The beds were comfortable and the bathrooms were clean. The hostess was very helpful and attentive when we had a question about the heat. Be aware the staircase to upstairs bedrooms and 2nd bathroom are...
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Interior

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.6 out of 10, Exceptional, (10)
"As advertised "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Majestic Mountain Side Sheffield/Great Barrington/SKI
Smart TV

Majestic Mountain Side Sheffield/Great Barrington/SKI

Majestic Mountain Side Sheffield/Great Barrington/SKI
Quintessential 6-BR Berkshires Lodge
Exterior

Quintessential 6-BR Berkshires Lodge

9.8 out of 10, Exceptional, (8)
"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "
Quintessential 6-BR Berkshires Lodge
Peaceful, Post and Beam Loft, Sleeps 9
1 bedroom, iron/ironing board, WiFi, bed sheets

Peaceful, Post and Beam Loft, Sleeps 9

10.0 out of 10, Exceptional, (14)
"House and grounds are large! Firepit is great! Local hiking and restaurants were fantastic! Enjoyed the large rooms and decor and artworks and prints."
Peaceful, Post and Beam Loft, Sleeps 9
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, (147)
"Highly recommend this house. Wonderful location, plenty of beds for a group. Great communication with the host."
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
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.

9.6 out of 10, Exceptional, (19)
"There was plenty of room for four families. Beds were comfy. If you plan on cooking you might want to bring your own knives and pans. Teflon pans were scraped . Only metal utensil available to flip pancakes. "
Amore Estate - beautiful room with many places to explore and relax in.
Hearts Desire is a furnished whole house in a small, colorful garden center.
Exterior detail

Hearts Desire is a furnished whole house in a small, colorful garden center.

10.0 out of 10, Exceptional, (86)
"It was gorgeous, and we had a wonderful cozy time. "
Hearts Desire is a furnished whole house in a small, colorful garden center.
A Grand property in Historic Stockbridge
Fridge, microwave, oven, stovetop

A Grand property in Historic Stockbridge

10.0 out of 10, Exceptional, (93)
"Property was beautiful and walkable to town. House is old but very nice. Large enough to accommodate 9 women! Loved sitting outside enjoying perfect weather! All in all had a wonderful experience!"
A Grand property in Historic Stockbridge
Dancing Horse Lodge
Fridge, microwave, oven, stovetop

Dancing Horse Lodge

9.4 out of 10, Exceptional, (38)
"We had a great stay with our family. Clean and close to where my daughter lives."
Dancing Horse Lodge
Minutes from downtown Great Barrington, Convenient location
Exterior

Minutes from downtown Great Barrington, Convenient location

10.0 out of 10, Exceptional, (43)
"Lovely home in a great location which fit our needs well. It was in great condition and quite comfortable.Wish we had more time to enjoy as there is so much to do in the area."
Minutes from downtown Great Barrington, Convenient location
Stockbridge Home: Walk to Town Beach!
Fridge, microwave, stovetop, dishwasher

Stockbridge Home: Walk to Town Beach!

9.8 out of 10, Exceptional, (10)
"A friend and I stayed at this property when the Trauma Healing Immersion event at Kripalu had them fully booked. As someone who normally stays at Kripalu when attended events I was hesitant to find property close enough to create an experience that was still as full of peace and solace as I am used to. This property was just what the dr. ordered. I love the bathroom remodel! It was quiet and peaceful which was just what we needed after a long day of lecture and experiential training. "
Stockbridge Home: Walk to Town Beach!
Stunning lake views and privacy only mins. to downtown Lenox, Stockbridge, Lee.
Property grounds

Stunning lake views and privacy only mins. to downtown Lenox, Stockbridge, Lee.

10.0 out of 10, Exceptional, (21)
"clean, wonderful views of the lake. "
Stunning lake views and privacy only mins. to downtown Lenox, Stockbridge, Lee.
5 Minutes from Catamount Ski Area
Outdoor dining

5 Minutes from Catamount Ski Area

9.0 out of 10, Wonderful, (20)
"Older house with lots of character. We were there during a hot and humid spell and the upstairs was on the stuffy side but we were able to open most of the windows and get decent ventilation. There is a mini-split with AC in the kitchen but we had a hard time getting it to cool most of the house. We were in the area for a concert at Tanglewood and it was an easy drive. Overall a great little spot just probably a more comfortable stay in the fall and winter."
5 Minutes from Catamount Ski Area
Gorgeous Lake Ashmere Home with Private Hot Tub & Lake Views, Screened Porch
TV, books, offices, printers

Gorgeous Lake Ashmere Home with Private Hot Tub & Lake Views, Screened Porch

10.0 out of 10, Exceptional, (18)
"We enjoyed a long weekend at this beautiful home. We had plenty of room for us to spread out. The kitchen is well stocked. They had games in the basement which were an added bonus. The beds were comfortable. We enjoyed relaxing on the porch in the evenings. We would definitely stay here again."
Gorgeous Lake Ashmere Home with Private Hot Tub & Lake Views, Screened Porch
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, (1751)
"So enjoyed this property and all the staff was always there to help in anyway!"
The price is AU$348
includes taxes & fees
5 Jan - 6 Jan
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, (922)
"It’s challenging to read the reviews and know what to expect for this hotel. One main reason for that is because each unit is owned by different owners. Some units may have been renovated more recently than other units. I booked 3 rooms. One unit had an old electric stove with coils while the other had a newer electric stove. 1 had a toaster oven while the others did not. We brought food to cook, but kept it simple because we didn’t know what cooking pots and utensils would be available. One...
The price is AU$334
includes taxes & fees
5 Jan - 6 Jan
Jiminy Peak Mountain Resort
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
TV, fireplace, DVD player

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (39)
"We had a wonderful stay. The cabin was clean and comfortable! "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
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.