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The Berkshires Vacation Rentals

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In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in The Berkshires

Lobby
Vacation Village in the Berkshires

Condo in Williamstown

3.0 star property
8.8 out of 10, Excellent, (2160)
"Great stay and beautiful scenery close to Jiminy’s Peak Ski slopes. They have a heated pool for winter weather and extra outdoor for the summer plus other family oriented amenities"
United States
Karla
$101 nightly
The price is $113
Dec 7 - Dec 8
Total with taxes and fees
Vacation Village in the Berkshires
Exterior
Jiminy Peak Mountain Resort

Condo resort in Hancock

3.0 star property
8.2 out of 10, Very Good, (986)
"This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay."
United States
Amy
$189 nightly
The price is $211
Dec 4 - Dec 5
Total with taxes and fees
Jiminy Peak Mountain Resort
Exterior
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

Apartment in Hancock

9.8 out of 10, Exceptional, (7)
"Everything was wonderful…"
United States
Alyne K.
$233 nightly
The price is $260
Dec 23 - Dec 24
Total with taxes and fees
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Indoor pool, outdoor pool, pool umbrellas, sun loungers
The Ponds at Foxhollow

Condo resort in Lenox

3.0 star property
8.6 out of 10, Excellent, (135)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
United States
Cyril
$125 nightly
The price is $140
Dec 5 - Dec 6
Total with taxes and fees
The Ponds at Foxhollow
Exterior
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Apartment in Hancock

10.0 out of 10, Exceptional, (8)
"We had a wonderful 3 day weekend! Perfect location for families."
United States
Eric B.
$210 nightly
The price is $235
Dec 9 - Dec 10
Total with taxes and fees
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Exterior
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Apartment in Hancock

10.0 out of 10, Exceptional, (23)
"This property is spacious, clean and well- appointed. I would stay here again!"
United States
Amanda M.
$210 nightly
The price is $235
Dec 9 - Dec 10
Total with taxes and fees
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
TV, DVD player, books
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Apartment in Hancock

10.0 out of 10, Exceptional, (3)
"We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!"
United States
Jen B.
$210 nightly
The price is $235
Dec 9 - Dec 10
Total with taxes and fees
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Fridge, microwave, oven, stovetop
Cozy Rustic Apt in 18th c Berkshire Farmhouse

Apartment in Lanesborough

9.6 out of 10, Exceptional, (67)
"Great value, so much better than all the touristy motels in the area!"
United States
Chris G.
$185 nightly
The price is $203
Dec 8 - Dec 9
Total with taxes and fees
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Exterior
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Apartment in Hancock

9.6 out of 10, Exceptional, (30)
"Great and clean property! Very easy to access and good parking too."
United States
Todd A.
$293 nightly
The price is $327
Dec 9 - Dec 10
Total with taxes and fees
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Exterior
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Vacation Home in Hancock

9.8 out of 10, Exceptional, (72)
"Great communication. Lots of games for the kids. Comfortable beds. Great living and game room. "
United States
Samuel R.
$490 nightly
The price is $547
Dec 4 - Dec 5
Total with taxes and fees
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Pool
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

Condo in Hancock

8.0 out of 10, Very Good, (8)
"Perfect spot for Mountain Adventures, property was well equipped with comfortable necessities. It was very clean and spacious for six people, 3 adults and 3 young boys. We would definitely stay again. "
United States
PK N.
$303 nightly
The price is $338
Dec 9 - Dec 10
Total with taxes and fees
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Outdoor dining
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Vacation Home in Sherwood Forest

10.0 out of 10, Exceptional, (4)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$337 nightly
The price is $376
Dec 8 - Dec 9
Total with taxes and fees
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Outdoor dining
2-Bdr Apt In Town, By the Water

Apartment in Williamstown

9.6 out of 10, Exceptional, (11)
"Lovely property, in good shape. Close to many Williamstown attractions."
United States
Scott M.
2-Bdr Apt In Town, By the Water
TV
Florida Mountain Log Cabin

Vacation Home in Florida

2.0 star property
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
$316 nightly
The price is $339
Dec 4 - Dec 5
Total with taxes and fees
Florida Mountain Log Cabin
Interior
UNIQUE - 1BR Country Condo @ Jiminy Peak

Condo in Hancock

10.0 out of 10, Exceptional, (14)
"Clean, comfortable place with nice amenities. "
United States
Mike H.
$504 nightly
The price is $563
Dec 6 - Dec 7
Total with taxes and fees
UNIQUE - 1BR Country Condo @ Jiminy Peak
Exterior
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Vacation Home in Sherwood Forest

9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
$351 nightly
The price is $392
Dec 15 - Dec 16
Total with taxes and fees
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Exterior
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Cabin in Hinsdale

9.8 out of 10, Exceptional, (34)
"Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay"
United States
Lindsey E.
$388 nightly
The price is $433
Dec 8 - Dec 9
Total with taxes and fees
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
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 The Berkshires Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Perfect "
Peter 2-night trip
Posted 2 days ago
Hotel Downstreet, an Ascend Collection Hotel

Find out more about The Berkshires

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