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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 320 Vacation Homes in New Lebanon with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (239)
"Property was very nice Kirchen could use some additons -starting with a ladle "
The price is AED 551
AED 841 total
includes taxes & fees
25 Feb - 26 Feb
Berkshire Village Carriage House - Super Private!!
Spectacular views and close to Great Barrington.
Private kitchen

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.
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna
Pool

Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

10.0 out of 10, Exceptional, (24)
"Beautiful, remote property perfect for large groups! We'll definitely try get back there in the summer!"
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna
Beautiful Berkshire Farm House on 160+ Acres
Exterior

Beautiful Berkshire Farm House on 160+ Acres

10.0 out of 10, Exceptional, (37)
"The house was great. Plenty of bedrooms to fit our party of 16 (mix of kids and adults). Very comfortable hang out spaces and places to play games. The barn with the basketball court was awesome also! We got a lot of use out of that. The house was clean and everything worked well except that the dishwasher was broken. That was unfortunate, but these things happen, and we made due. The owner said that it would be fixed in a week or so, so hopefully not an issue for anyone else. Owner was...
Beautiful Berkshire Farm House on 160+ Acres
Amore Estate - beautiful room with many places to explore and relax in.
October MNT FARM!!

Amore Estate - beautiful room with many places to explore and relax in.

9.4 out of 10, Exceptional, (21)
"Fantastic, large house with tons of places to explore in the house and on the property. We came for a long weekend with 3 families and both the adults and kids felt quickly at home and really enjoyed our stay. We cannot wait to some back!"
Amore Estate - beautiful room with many places to explore and relax in.
Comfortable Berkshires retreat on mtn resort, SISO
Exterior

Comfortable Berkshires retreat on mtn resort, SISO

The price is AED 1,183
AED 2,472 total
includes taxes & fees
24 Feb - 25 Feb
Comfortable Berkshires retreat on mtn resort, SISO
4 Bdrm Modern Victorian with Tree House and playground
Gorgeous chef with 6 burner professional gas range

4 Bdrm Modern Victorian with Tree House and playground

9.8 out of 10, Exceptional, (106)
"Great house"
4 Bdrm Modern Victorian with Tree House and playground
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Comfortable New Decor in Living Room Equipped w Smart TV and Deck

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

10.0 out of 10, Exceptional, (66)
"Location was very Close to trail"
The price is AED 1,153
AED 2,229 total
includes taxes & fees
24 Feb - 25 Feb
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Home in Great Barrington
Interior

Home in Great Barrington

9.6 out of 10, Exceptional, (19)
"Our family had a wonderful experience and stay. "
The price is AED 790
AED 1,219 total
includes taxes & fees
19 Mar - 20 Mar
Home in Great Barrington
Country Living just minutes from Everything!
It may be cold outside, but it's warm & cozy inside!

Country Living just minutes from Everything!

10.0 out of 10, Exceptional, (27)
"Very nice, very clean property. Everything you need. Communication with owner is excellent. My family and I were extremely comfortable here!"
Country Living just minutes from Everything!
Hearts Desire is a furnished whole house in a small, colorful garden center.
Exterior

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

10.0 out of 10, Exceptional, (88)
"We thoroughly enjoyed our stay at “Hearts Desire”! Everything was set up for our relaxation and enjoyment! The weather outside was terrible but the atmosphere in the house was warms and so comfortable. We were able to enjoy watching the tv which sometimes doesn’t give many choices in some other stays. We are definitely getting the game “Fake News or Not”! Lots of fun. If we plan on visiting the area again, we will definitely return! Thank you!"
Hearts Desire is a furnished whole house in a small, colorful garden center.
BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!
Start Your Day Right - Enjoy Complimentary Fresh Bagels From Around the Corner!

BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!

2.0 star property
8.8 out of 10, Excellent, (3)
"Property is lovely and very well maintained. We stayed for over 10 days and it was a perfect home away from home. Owners are very kind and accommodating — when I couldn’t find a hair dryer one was delivered to the house within a couple of hours. They also offered to relocate us if we were bothered by the nearby forest fire, which was not necessary. I hope we’ll have the opportunity to stay again."
BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!
Hudson Valley and The Berkshires getaway
Kitchen and dining room

Hudson Valley and The Berkshires getaway

10.0 out of 10, Exceptional, (5)
Hudson Valley and The Berkshires getaway
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Marina

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.
Hancock Village Inn at Jiminy Peak
Hancock Village Inn in Winter

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (9)
"Annual mother/son ski and food fest!Lots of fun with family and friends. Plenty of space for everyone.. Kitchen wascwell"
The price is AED 2,196
AED 3,898 total
includes taxes & fees
25 Feb - 26 Feb
Hancock Village Inn at Jiminy Peak
Quintessential 6-BR Berkshires Lodge

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (11)
"The house was perfect for us. Spacious, clean, comfortable. Beds comfortable. Bathrooms really nice. The road in the development is dirt, a 4wd is needed as stated. It was muddy and rutty on arrival, then snow and ice , but do-able. Great house. Would recommend "
Quintessential 6-BR Berkshires Lodge
Chic Pittsfield Home With A View!

Chic Pittsfield Home With A View!

8.6 out of 10, Excellent, (10)
"This property was just as shown in the listing and met our needs very well. It was well appointed and had many inviting areas to gather and relax in. The kitchen was well equipped and easy to use. Some very nice touches with closets and bathroom storage areas that made staying there user friendly. "
Chic Pittsfield Home With A View!
Wellspring by AvantStay | Indoor Pool + Views
Welcome!

Wellspring by AvantStay | Indoor Pool + Views

10.0 out of 10, Exceptional, (10)
"We all enjoyed our stay. The house and indoor pool were wonderful. There are plenty of comfortable places to sit and enjoy the gorgeous views. We loved the location which is both close to Lenox restaurants, as well as, the southern Berkshires for food markets and activities for kids. The property manager was attentive, and the owner was very responsive. We loved our week at this family friendly property and highly recommend it. "
Wellspring by AvantStay | Indoor Pool + Views
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Breakfast Nook - wake up to the best sunshine ever!

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

10.0 out of 10, Exceptional, (118)
"Property as described. Great location to towns. Larger interior space than anticipated. Great Kitchen for a group of 5 to cook, chat and enjoy! Overall a warm and spacious home for old college friends to reunite. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
5 Minutes from Catamount Ski Area
Dining

5 Minutes from Catamount Ski Area

9.0 out of 10, Wonderful, (21)
"Cozy spot after skiing. "
5 Minutes from Catamount Ski Area
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 New Lebanon

Near Tanglewood: Historic Summer Retreat
Living area

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (19)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
The price is AED 441
AED 1,192 total
includes taxes & fees
27 Feb - 28 Feb
Near Tanglewood: Historic Summer Retreat
Experience the Beauty of the Berkshires and Hudson Valley in Our Historic Home
Outdoor dining

Experience the Beauty of the Berkshires and Hudson Valley in Our Historic Home

9.2 out of 10, Wonderful, (10)
"Simply loved the property! Enjoyed relaxing on the porch and sitting by the waterfall. Location was central to other sites we wanted to visit, too! We lost power overnight in the storm but made it work. Owner kept in contact with us and even started working on alternatives for us! Ran to get batteries for the lantern the house had and ice for the cooler to save our food! A few more candles and flashlights would have been great, but otherwise, a gem! Thku for your hospitality!"
Experience the Beauty of the Berkshires and Hudson Valley in Our Historic Home
Vacation Village in the Berkshires
Exterior

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1766)
"Great place for a family vacation. Property very clean, quiet, and well organized "
The price is AED 400
AED 476 total
includes taxes & fees
4 Mar - 5 Mar
Vacation Village in the Berkshires
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.