Photo by Leah Dalley

New Lebanon Holiday Rentals

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in New Lebanon

Near Tanglewood: Historic Summer Retreat
Fridge, microwave, oven, stovetop

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (15)
"This was a beautiful, spacious, and peaceful place for us in our friends to get together. It was centrally located to everything we wanted to do. Amanda was wonderful in her communications and everything was clean and ready for us."
The price is HK$1,245
HK$2,902 total
includes taxes & fees
25 Nov - 26 Nov
Near Tanglewood: Historic Summer Retreat
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, (1746)
"Property was beautiful, great staff "
The price is HK$1,313
HK$1,519 total
includes taxes & fees
25 Nov - 26 Nov
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, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is HK$1,160
HK$1,272 total
includes taxes & fees
25 Nov - 26 Nov
Jiminy Peak Mountain Resort
Micosta Leisure Inn
Balcony

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (89)
"Fantastic place to stay! So homey, comfortable, and peaceful. Steven was a fabulous host, and his property is wonderful - in a beautiful garden. The room is large and beyond well equipped. No reason to pay more to stay downtown Hudson. We’re on a month-long New England road trip, and this has been our favorite stay! "
The price is HK$899
HK$971 total
includes taxes & fees
26 Nov - 27 Nov
Micosta Leisure Inn
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (225)
"One of the best properties i've ever stayed at "
The price is HK$1,113
HK$1,721 total
includes taxes & fees
25 Nov - 26 Nov
Berkshire Village Carriage House - Super Private!!
Private Estate, Heated YEARROUND Outdoor Pool
Fridge, microwave, oven, stovetop

Private Estate, Heated YEARROUND Outdoor Pool

10.0 out of 10, Exceptional, (13)
"The country setting provided a quiet retreat. The home is well equipped: plenty of beds, multiple gathering places, pool with towels (although it was pretty cold until the pool guy came and provided help). The outdoor grill provides additional cooking space. The home is within easy driving to many places of interest. We had a nice week at this home."
Private Estate, Heated YEARROUND Outdoor Pool
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
TV, fireplace, DVD player, books

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (41)
"We had expectations of a peaceful rustic cabin in the woods, and this rental checked almost all of the boxes! The quaint town of Great Barrington was just close enough for convenience, but the house was rural enough to help us all relax and enjoy the quiet. We loved the dock and the firepit, and the house was well-stocked with firewood, towels, and toiletries. "
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Berkshires Cabin 2 Mi to Appalachian Trail!
TV, fireplace, books

Berkshires Cabin 2 Mi to Appalachian Trail!

9.8 out of 10, Exceptional, (9)
"Enjoyed the foliage and some nice hikes. House was comfortable and clean. Owner was responsive and helpful. We arrived at night and had trouble locating the property when our gps failed. Owner was helpful guiding us to the house. I suggest arriving in the light of day. "
Berkshires Cabin 2 Mi to Appalachian Trail!
Berkshire Lake access
Lake

Berkshire Lake access

10.0 out of 10, Exceptional, (47)
"The house was very clean and the yard is large. It's a great place for family vacations."
Berkshire Lake access
Quintessential 6-BR Berkshires Lodge
Exterior

Quintessential 6-BR Berkshires Lodge

9.8 out of 10, Exceptional, (8)
"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "
Quintessential 6-BR Berkshires Lodge
Beautiful One-of-a Kind Private Estate! Pool, Gym, Arcade, Trails, Pond, Library
Fridge, microwave, oven, stovetop

Beautiful One-of-a Kind Private Estate! Pool, Gym, Arcade, Trails, Pond, Library

9.6 out of 10, Exceptional, (84)
"This large home has many comfortable bedrooms, some very large suites. The kitchen is very well stocked. Our family had a wonderful stay. The pool was great, and a center of our enjoyment. Kids also enjoyed the game room."
Beautiful One-of-a Kind Private Estate! Pool, Gym, Arcade, Trails, Pond, Library
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Dining

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

10.0 out of 10, Exceptional, (116)
"As with our previous several stays, we thoroughly enjoyed the comfort and location of the house. We had a great time and can’t wait to do it all over again next Summer. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
3 Bedroom Lakefront Home with Hot Tub & Fireplace
View from property

3 Bedroom Lakefront Home with Hot Tub & Fireplace

10.0 out of 10, Exceptional, (107)
"Very glad to have found Nana’s Place. It’s been perfect for us every time. Thank you!"
3 Bedroom Lakefront Home with Hot Tub & Fireplace
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, (16)
"We were a big group..16 adults and 7 children. The families with children were well situated with nearby or adjacent rooms. Everyone had comfortable rooms which afforded privacy and quiet times. Each room had its own beautiful newly renovated bathrooms ( with great water pressure). The living and dining rooms were large and comfortable. The dining table was a loooong table with benches all around which easily sat our crowd. The backyard was gorgeous with beautiful views of the distant mountains....
The Kemble- Built by a US Secretary of State in Lenox
Stockbridge Home, Come Experience The Berkshires!
Fridge, microwave, oven, stovetop

Stockbridge Home, Come Experience The Berkshires!

10.0 out of 10, Exceptional, (24)
"We enjoyed everything about this lovely house in the Berkshires--the latest appliances, thoughtful details (throws on all the beds and sofas), a great backyard. Would highly recommend! "
Stockbridge Home, Come Experience The Berkshires!
Chic Pittsfield Home With A View!
Property grounds

Chic Pittsfield Home With A View!

8.8 out of 10, Excellent, (8)
"Great view from the property, lovely house and yard. Coiuldn't have been a better stay. "
Chic Pittsfield Home With A View!
The Winthrop Estate - 12K SF 32 Acres
Exterior

The Winthrop Estate - 12K SF 32 Acres

10.0 out of 10, Exceptional, (4)
"Everyone enjoyed the stay"
The Winthrop Estate - 12K SF 32 Acres
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Exterior

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

10.0 out of 10, Exceptional, (23)
"My partner and I really enjoyed our relaxing stay at this quaint cottage. It was clean, comfortable, and tucked away in a very quiet area. It was easy to get to restaurants and theaters in Pittsfield / Lenox / Stockbridge. The hot tub was also a great way to spend a cozy fall afternoon!"
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
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.

9.8 out of 10, Exceptional, (17)
"Beautiful, spacious house in a great location!"
Amore Estate - beautiful room with many places to explore and relax in.
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Terrace/patio

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

9.4 out of 10, Exceptional, (59)
"Cute and comfy place, great location. We walked to dinner twice and enjoyed how convenient this place was to all of the Berkshires. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
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.
Don't see what you're looking for?
See all available properties in New Lebanon
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in New Lebanon you may be interested in

Hyatt Place Albany/Downtown
Reception

Hyatt Place Albany/Downtown

3.0 star property
8.8 out of 10, Excellent, (717)
"Great location. The hotel was clean and the room was cozy!! "
The price is HK$860
HK$980 total
includes taxes & fees
7 Dec - 8 Dec
Hyatt Place Albany/Downtown
Comfort Inn Glenmont - Albany South
Lobby

Comfort Inn Glenmont - Albany South

2.5 star property
7.8 out of 10, Good, (891)
"Great spot and just 8 minutes to downtown Albany. I had a good night sleep 😴 enjoy"
The price is HK$710
HK$809 total
includes taxes & fees
22 Dec - 23 Dec
Comfort Inn Glenmont - Albany South
Hotel Downstreet
Hypo-allergenic bedding, laptop workspace, blackout curtains

Hotel Downstreet

3.0 star property
8.6 out of 10, Excellent, (1043)
"Great location, wonderful staff, fun pool and cool art. Would definitely stay again! "
The price is HK$904
HK$1,009 total
includes taxes & fees
5 Dec - 6 Dec
Hotel Downstreet
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until December 4 with our Black Friday deals. Stay by December 15, 2025.
Unlock Black Friday deals

Frequently asked questions

Can I find holiday rentals in New Lebanon?

Yes, there are holiday rentals close to the most popular sights in New Lebanon, or you can select a more secluded option if you're looking for a relaxing stay. New Lebanon is known for its restaurants and shopping.

What are some of the best holiday rentals that New Lebanon has to offer?

Berkshire Village Carriage House - Super Private!!: This holiday home rental outside of New Lebanon is located in the mountains, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of books in this rental home to help you unwind.

How many holiday rentals are there in New Lebanon?

Expedia has 8 holiday rentals for your stay in New Lebanon.

What’s there to see and do in New Lebanon?

Shatford Memorial Park and Japanese Knotweed are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Mount Lebanon Shaker Village and New Lebanon Library.

What’s a holiday rental in New Lebanon like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in New Lebanon. Holiday rentals feature amenities like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from public hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for a small group gathering.