Holiday Rentals in Berkshire County

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Featured Holiday Rentals in Berkshire County

Our top choices for Berkshire County holiday rentals

Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1993)
"Beautiful location!"
The price is €92
includes taxes & fees
21 Sept - 22 Sept
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, (973)
"I loved everything, pretty clean. The play areas are so cool. "
The price is €152
includes taxes & fees
15 Sept - 16 Sept
Jiminy Peak Mountain Resort
Huttopia Berkshires
Restaurant

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (4)
"Perfect place for a relaxing getaway! We loved everything! "
The price is €93
includes taxes & fees
9 Sept - 10 Sept
Huttopia Berkshires
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (128)
"We were 4 adult friends sharing a 2-bedroom and enjoyed the size of the space and the location of the condo was under a 10 min drive to all the sights"
The Ponds at Foxhollow
The Kemble- Built by a US Secretary of State in Lenox
Exterior detail

The Kemble- Built by a US Secretary of State in Lenox

10.0 out of 10, Exceptional, (17)
"Loved the property. Perfect for our gathering."
The Kemble- Built by a US Secretary of State in Lenox
Hancock Village Inn at Jiminy Peak
Exterior

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (13)
"Amazing Inn. Cozy and everything we needed. "
The price is €973
includes taxes & fees
9 Sept - 10 Sept
Hancock Village Inn at Jiminy Peak
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Exterior

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (222)
"Cabin was exactly what we were looking for in a weekend away. Great location, quiet, and had everything we needed. Hope to go back again soon! "
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
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.

9.0 out of 10, Wonderful, (27)
"Beautiful, spacious house in a great location!"
Amore Estate - beautiful room with many places to explore and relax in.
Private Island - Largest Fresh Water Reservoir in Mass
Interior

Private Island - Largest Fresh Water Reservoir in Mass

8.8 out of 10, Excellent, (8)
"We had a great time. The owner Bill was a great host."
Private Island - Largest Fresh Water Reservoir in Mass
Comfortable Berkshires retreat on mtn resort, SISO
A heated pool

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is €414
includes taxes & fees
9 Sept - 10 Sept
Comfortable Berkshires retreat on mtn resort, SISO
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Outdoor dining

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (146)
"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Guesthouse Cabin vacation rentals in Berkshire County
Dining

Guesthouse Cabin vacation rentals in Berkshire County

10.0 out of 10, Exceptional, (9)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
The price is €654
includes taxes & fees
30 Sept - 1 Oct
Guesthouse Cabin vacation rentals in Berkshire County
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Property grounds

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.8 out of 10, Exceptional, (18)
"Very friendly hosts, great location. "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Contemporary Berkshire Home with Views of Taconic Golf Course
Smart TV, fireplace, DVD player, books

Contemporary Berkshire Home with Views of Taconic Golf Course

10.0 out of 10, Exceptional, (6)
Contemporary Berkshire Home with Views of Taconic Golf Course
Florida Mountain Log Cabin!
TV

Florida Mountain Log Cabin!

2.0 star property
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
The price is €381
includes taxes & fees
9 Sept - 10 Sept
Florida Mountain Log Cabin!
Park Street Penthouse Apartment
Games room

Park Street Penthouse Apartment

9.4 out of 10, Exceptional, (10)
"The penthouse was beautiful and spacious. The Host Lea was very congenial and offered great suggestions for the location. I will definitely be coming back "
The price is €234
includes taxes & fees
18 Sept - 19 Sept
Park Street Penthouse Apartment
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Smart TV, fireplace, DVD player

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

10.0 out of 10, Exceptional, (27)
"Spacious, welcoming, so well stocked, we felt lucky to find the property."
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
2200sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
Property grounds

2200sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

9.8 out of 10, Exceptional, (69)
"Beautiful location, very spacious, comfortable and clean."
2200sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Fridge, microwave, oven, stovetop

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

10.0 out of 10, Exceptional, (54)
"We loved Manor Lane! It had every amenity you could ask for. The house is fun and charming and there are thoughtful touches everywhere you look! We had fun watching movies in the living room, playing games in the lounge, cooking family meals in the spectacular kitchen and playing tennis in the sunshine. A perfect 10!"
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Enjoy comfortable elegance in this secluded grand home located in town
Exterior

Enjoy comfortable elegance in this secluded grand home located in town

10.0 out of 10, Exceptional, (72)
"Great location for access to both Tanglewood and Lenox center. "
Enjoy comfortable elegance in this secluded grand home located in town
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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Top Berkshire County Hotel Reviews

Find out more about Berkshire County

Find out more about Berkshire County

Holiday Homes in Berkshire County

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