Photo by Leah Dalley

Holiday Homes in New Lebanon

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
5 Sept - 7 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Featured Holiday Homes in New Lebanon

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

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (256)
"Host was very friendly and helpful. House was absolutely adorable and decorated well. Plenty of parking. Beautiful, well-maintained property. Great for hikes. Lovely fire pit area and lots of wood. Very convenient location to recreation in The Berkshires. I would stay here again. "
The price is AU$350
includes taxes & fees
16 Sept - 17 Sept
Berkshire Village Carriage House - Super Private!!
NEW RENO Historic Creamery in Berkshires w/hot tub
Terrace/patio

NEW RENO Historic Creamery in Berkshires w/hot tub

10.0 out of 10, Exceptional, (3)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
The price is AU$746
includes taxes & fees
17 Sept - 18 Sept
NEW RENO Historic Creamery in Berkshires w/hot tub
Near Tanglewood: Historic Summer Retreat
Fridge, microwave, oven, stovetop

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (22)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
The price is AU$796
includes taxes & fees
24 Aug - 25 Aug
Near Tanglewood: Historic Summer Retreat
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Terrace/patio

Historic Berkshires Home Near Tanglewood, Trails & Wineries

9.0 out of 10, Wonderful, (17)
"Of all the properties I have stayed at, this home is my favorite! Excited to be able to stay in a such a historical home in a rich historical area! Amanda was a wonderful host! Provided a comfortable stay. The home had all the necessities! The town has delicious places to eat. Grocery store is great! My hope is to return and spend more time here."
The price is AU$802
includes taxes & fees
5 Sept - 6 Sept
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Fridge, microwave, oven, stovetop

Sun Filled Lenox Retreat - Minutes to Tanglewood!

10.0 out of 10, Exceptional, (1)
"Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again."
The price is AU$797
includes taxes & fees
16 Sept - 17 Sept
Sun Filled Lenox Retreat - Minutes to Tanglewood!
All the comforts of home
Property grounds

All the comforts of home

9.0 out of 10, Wonderful, (24)
"Really liked staying at Steven’s place! The hot tub was a great touch. Stayed in Unit 1 - it’s small but perfect for what we needed it for! "
The price is AU$223
includes taxes & fees
2 Sept - 3 Sept
All the comforts of home
Home in Great Barrington
Fridge, microwave, oven, stovetop

Home in Great Barrington

9.8 out of 10, Exceptional, (23)
"Enjoyed our stay!!!"
The price is AU$476
includes taxes & fees
3 Sept - 4 Sept
Home in Great Barrington
Perfect House In Hillsdale, Brings Friends & Fam
Exterior

Perfect House In Hillsdale, Brings Friends & Fam

8.6 out of 10, Excellent, (4)
"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "
The price is AU$803
includes taxes & fees
24 Aug - 25 Aug
Perfect House In Hillsdale, Brings Friends & Fam
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Fridge, microwave, oven, stovetop

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

2.0 star property
9.0 out of 10, Wonderful, (4)
"Very clean and spacious! We enjoyed our stay with our small pup!"
The price is AU$842
includes taxes & fees
11 Sept - 12 Sept
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
North Getaway Cottage
Exterior

North Getaway Cottage

9.6 out of 10, Exceptional, (20)
"Claudia is such a considerate and thoughtful host! We felt so welcome and at ease."
The price is AU$707
includes taxes & fees
4 Sept - 5 Sept
North Getaway Cottage
Bungalow in the Berkshires
Exterior

Bungalow in the Berkshires

10.0 out of 10, Exceptional, (1)
"Renting this house was very last minute because the place we initially booked fell through - and we're so glad it did! The house was charming, cozy, up-to-date, and beautifully decorated. The neighborhood was nice and quiet, and the drive to downtown was short. I highly recommend this house!"
The price is AU$813
includes taxes & fees
24 Aug - 25 Aug
Bungalow in the Berkshires
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 AU$760
includes taxes & fees
10 Sept - 11 Sept
Comfortable Berkshires retreat on mtn resort, SISO
Bright & Airy 1 BDRM Private Apartment
Iron/ironing board, WiFi, bed sheets

Bright & Airy 1 BDRM Private Apartment

The price is AU$323
includes taxes & fees
8 Sept - 9 Sept
Bright & Airy 1 BDRM Private Apartment
3-bedroom house in beautiful Berkshires, close to amenities!
Property grounds

3-bedroom house in beautiful Berkshires, close to amenities!

The price is AU$504
includes taxes & fees
26 Aug - 27 Aug
3-bedroom house in beautiful Berkshires, close to amenities!
The Lakeshore House
Property grounds

The Lakeshore House

10.0 out of 10, Exceptional, (1)
"Excellent stay!"
The price is AU$1,259
includes taxes & fees
7 Sept - 8 Sept
The Lakeshore House
Hancock Village Inn at Jiminy Peak
Exterior

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (12)
"Very kinda hosts, and wonderful house."
The price is AU$1,645
includes taxes & fees
25 Aug - 26 Aug
Hancock Village Inn at Jiminy Peak
Glass Lake Cottage
Outdoor dining

Glass Lake Cottage

10.0 out of 10, Exceptional, (1)
"Glass lake cottage was the perfect relaxing retreat while I was visiting for a wedding at the Old Daley Inn! The place was clean, had a well stocked kitchen and everything I needed. We were lucky to catch a fantastic sunset and enjoyed the view from the large deck. Will definitely be back! "
Glass Lake Cottage
Great Barrington Get Away
Fridge, microwave, oven, stovetop

Great Barrington Get Away

9.4 out of 10, Exceptional, (23)
"The host was very communicative and responsive during our arrival and check out. The listing and everything was as it said we were very pleased with both the location of the home and the actual home itself and the property walking distance to town truly cannot say enough. Thank you for Your hospitality. Our family is very grateful. "
The price is AU$895
includes taxes & fees
3 Sept - 4 Sept
Great Barrington Get Away
Treat yourself at the stunning June Farms Wellness Huts!
Terrace/patio

Treat yourself at the stunning June Farms Wellness Huts!

10.0 out of 10, Exceptional, (8)
"The wellness hut was an amazing getaway. Beautiful interior and design. Loved the little outdoor sauna. Loved the front porch/deck. Would definitely return for another stay."
The price is AU$725
includes taxes & fees
22 Sept - 23 Sept
Treat yourself at the stunning June Farms Wellness Huts!
Honey Comb Hideout 3Br. House Albany
Private kitchen

Honey Comb Hideout 3Br. House Albany

The price is AU$680
includes taxes & fees
23 Aug - 24 Aug
Honey Comb Hideout 3Br. House Albany
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top New Lebanon Hotel Reviews

The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

10/10 Excellent
"We had a good stay at the Black Swann Inn. I think some of the mixed comments can be understood in terms of expectations. It is. It a quaint New England inn with a common room and cushy furniture. It is more like a holiday inn. With that understanding it does its job - it is clean, comfortable and has the bonus of outdoor space on the lake with Adirondack chairs and boat rentals. "
Matthew 1-night trip
Posted 22 hours ago
The Black Swan Lee - Lenox, Ascend Hotel Collection