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Check prices for these dates

Next weekend
31 Jan - 2 Feb
In two weeks
7 Feb - 9 Feb
In one month
21 Feb - 23 Feb
In two months
21 Mar - 23 Mar
18th century Berkshires farmhouse on 12 acres, impeccably updated.
Terrace/patio

18th century Berkshires farmhouse on 12 acres, impeccably updated.

18th century Berkshires farmhouse on 12 acres, impeccably updated.
Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys!
Books

Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys!

9.6 out of 10, Exceptional, (14)
"Apartment was clean, bright with comfortable beds. Great location for Berkshires visit, close to Tanglewood and all places fun. Only drawback for us (me and two college friends) was that we brought food for breakfasts and it’s not set up for eating in. No sink in the small kitchen so paper plates and plastic utensils are provided. Small but useful refrigerator. Only a microwave. Small coffee maker but Jodi nicely provided lots of coffee so we weren’t ornery in the morning! Brought in picnic food...
Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys!
Charming Farmhouse - quiet, private & peaceful
Property grounds

Charming Farmhouse - quiet, private & peaceful

9.6 out of 10, Exceptional, (62)
"Was a beautiful old farm house, very private location and exactly what we where looking for!"
Charming Farmhouse - quiet, private & peaceful
Experience a charming 3 bedroom farm stay close to winter activity.
Exterior

Experience a charming 3 bedroom farm stay close to winter activity.

10.0 out of 10, Exceptional, (26)
"Old house with new amenities - love the charm of this western MA home. Our family of five stayed here for a nearby wedding and it was effortless including checkout! Host was very accommodating as well."
The price is HK$1,597
HK$2,600 total
includes taxes & fees
23 Jan - 24 Jan
Experience a charming 3 bedroom farm stay close to winter activity.
Country living with hill town views above the clouds!
Property grounds

Country living with hill town views above the clouds!

Country living with hill town views above the clouds!
Large, family-friendly farmhouse located in the beautiful Berkshires
Outdoor dining

Large, family-friendly farmhouse located in the beautiful Berkshires

9.8 out of 10, Exceptional, (31)
"The Hart's family have a beautiful home full of wonderful historical artifacts, comfortable furniture, and well stocked kitchen and bathrooms. We loved the wide plank floors, working fireplace, and modern day wifi. Thank you for sharing this wonderful property."
Large, family-friendly farmhouse located in the beautiful Berkshires
Charming Farmhouse; 2 Bed / 2 Bath, only 1.5 miles to Jiminy Peak. Pet Friendly.
Property grounds

Charming Farmhouse; 2 Bed / 2 Bath, only 1.5 miles to Jiminy Peak. Pet Friendly.

9.0 out of 10, Wonderful, (2)
"A very quaint and well appointed house in a lovely neighborhood."
Charming Farmhouse; 2 Bed / 2 Bath, only 1.5 miles to Jiminy Peak. Pet Friendly.
Stunning views on 545 acres at end of dirt road
Property grounds

Stunning views on 545 acres at end of dirt road

10.0 out of 10, Exceptional, (48)
"This house and property are amazing! Everything was clean, well stocked and there were even hiking trails. Owners were easy to communicate with and helpful!"
Stunning views on 545 acres at end of dirt road
Rural charm a mile from Berkshire East Ski Resort and 29 miles from Mt. Snow.
Property grounds

Rural charm a mile from Berkshire East Ski Resort and 29 miles from Mt. Snow.

10.0 out of 10, Exceptional, (12)
"Our group met at this charming, comfortable home for a family reunion. Charlemont is a quintessential New England town that offers gorgeous views and plenty of outdoor activities. We grew up close by, and skied Berkshire East, so it was fun to revisit the area. The host was happy to share her local knowledge and more than accommodating. We'd highly recommend staying at The Parsonage."
Rural charm a mile from Berkshire East Ski Resort and 29 miles from Mt. Snow.
Historic 1817 Berkshire Farmhouse- Close to Everything!
Aerial view

Historic 1817 Berkshire Farmhouse- Close to Everything!

10.0 out of 10, Exceptional, (1)
"A sweet little farm house perfect for a long weekend getaway. We love the lofty primary bed room and excellent mattress, exposed beams and well-supplied and modern kitchen. Great location between Lee and Lenox, made it easy to get all around the Berkshires. All the equipment and appliances m the house were clean and updated. Quiet neighborhood, lovely and large state forest right close by. "
Historic 1817 Berkshire Farmhouse- Close to Everything!
Farmhouse on Otis Pond
Property grounds

Farmhouse on Otis Pond

10.0 out of 10, Exceptional, (1)
"We had a wonderful time at the farmhouse. It is a charming old home. Our son loved being able to wake up and go fishing. The owner quickly responded to any questions. I loved sitting on the porch swing and listening to the birds."
Farmhouse on Otis Pond
18th century 3-bedroom renovated farmhouse in peaceful Whately with WiFi, AC
Microwave, oven, stovetop, dishwasher

18th century 3-bedroom renovated farmhouse in peaceful Whately with WiFi, AC

10.0 out of 10, Exceptional, (1)
"We were happy to find such a large, comfortable home. The owner was very helpful. Lovely stay"
18th century 3-bedroom renovated farmhouse in peaceful Whately with WiFi, AC
1847 New Marlborough Farmhouse. a 4-BR home right in our quiet village.
Private kitchen

1847 New Marlborough Farmhouse. a 4-BR home right in our quiet village.

1847 New Marlborough Farmhouse. a 4-BR home right in our quiet village.
Charming 3-bedroom farmhouse in fantastic Northfield with WiFi, AC
Interior

Charming 3-bedroom farmhouse in fantastic Northfield with WiFi, AC

2.0 star property
The price is HK$1,751
HK$3,084 total
includes taxes & fees
24 Jan - 25 Jan
Charming 3-bedroom farmhouse in fantastic Northfield with WiFi, AC
10 Minutes to Ski Butternut! Dogs Welcome!
Exterior

10 Minutes to Ski Butternut! Dogs Welcome!

10 Minutes to Ski Butternut! Dogs Welcome!
Secluded 19th century Farmhouse with mountain views
Exterior

Secluded 19th century Farmhouse with mountain views

10.0 out of 10, Exceptional, (1)
"We had a great time on our recent trip to Berkshires. It was due largely in part because of some excellent and charming accomodations at Jeff's family farmhouse. Our large group loved the farmhouse's layout, old world charm and beautiful property."
Secluded 19th century Farmhouse with mountain views
Beautiful Berkshires Farmhouse with game room and plenty of room
Fridge, microwave, oven, stovetop

Beautiful Berkshires Farmhouse with game room and plenty of room

Beautiful Berkshires Farmhouse with game room and plenty of room
ONTARA....
Exterior

ONTARA....

ONTARA....
New 4500 sq ft modern 5 bed-5.5 bath on Housatonic River and walk to Stockbridge
Fridge, microwave, oven, stovetop

New 4500 sq ft modern 5 bed-5.5 bath on Housatonic River and walk to Stockbridge

2.0 star property
10.0 out of 10, Exceptional, (6)
"We recently rented this house for two weeks in order to spend time under the same roof with our grown children and baby grandson - and we couldn't have had a more enjoyable time! The house provided ample space for us to gather in small groups or larger ones whether we were indoors, outside on the deck or in the yard. The location in town was ideal for pushing the baby stroller along all the sidewalks as well as easily accessing all the shops and restaurants. With the Red Lion Inn only a block...
New 4500 sq ft modern 5 bed-5.5 bath on Housatonic River and walk to Stockbridge
Renovated Berkshires Farmhouse - minutes from hiking, swimming, and Tanglewood
Exterior

Renovated Berkshires Farmhouse - minutes from hiking, swimming, and Tanglewood

Renovated Berkshires Farmhouse - minutes from hiking, swimming, and Tanglewood
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 Western Massachusetts

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, (1757)
"It had a great pool and hot tub. also right near the ski area, jiminey Peak."
The price is HK$1,459
HK$1,678 total
includes taxes & fees
28 Jan - 29 Jan
Vacation Village in the Berkshires
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)
"A nice cabin in the woods. Only issue was rodents at the property. We had four sighting in three days. Would stay again if they resolved the mouse problem."
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
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, (33)
"We had a wonderful stay for our mother’s birthday with her 4 children and 10 of her 12 grandchildren. There was plenty to do for everyone especially with a 75 year difference in ages!!"
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.