New Lebanon holiday homes

We found 463 holiday rentals — enter your dates for availability
Discover a selection of 12 homes and other holiday rentals in New Lebanon that are perfect for your trip. Holiday homes provide the best amenities for your stay with friends, family or just your pet, such as parking and air conditioning. No matter what you're looking for, you'll find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – New Lebanon

Showing deals for:20 Nov - 27 Nov

Queen bedroom
Terrace/patio
Dining room with butcher block table
Property grounds
Exceptional
(102 reviews)

Vacation in a Berkshire Farmhouse

West Stockbridge

8% off
NZ$4,842
for 7 nights, 1 home
NZ$692 per night
includes taxes & fees
Vacation in a Berkshire Farmhouse
Property grounds
Private kitchen
Dining
Interior
Exceptional
(5 reviews)

Dog Friendly Country Farmhouse, 2 bed / 2 bath; 1.5 miles from Jiminy Peak

Williamstown

20% off
NZ$3,458
for 7 nights, 1 room
NZ$494 per night
includes taxes & fees
Dog Friendly Country Farmhouse, 2 bed / 2 bath; 1.5 miles from Jiminy Peak
Outdoor dining
Kitchen with counter seating for 4- door on the right to garage
View from entry into living room- perfect spot for relaxing!
Property grounds
Exceptional
(9 reviews)

Sophisticated Lenox Retreat by Evergreen Home

Lenox

11% off
NZ$6,791
for 7 nights, 1 home
NZ$970 per night
includes taxes & fees
Sophisticated Lenox Retreat by Evergreen Home
Outdoor dining
Living area
Interior
Interior
Exceptional
(35 reviews)

Renovated Pittsfield Colonial by Evergreen Home

Pittsfield

11% off
NZ$7,564
for 7 nights, 1 home
NZ$1,081 per night
includes taxes & fees
Renovated Pittsfield Colonial by Evergreen Home
Open plan dining area with water views and access to the sunroom
view from the 2nd bedroom
View of the lower deck from the sunroom
View from the lawn by the water
Exceptional
(65 reviews)

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield

8% off
NZ$8,310
for 7 nights, 1 home
NZ$1,187 per night
includes taxes & fees
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Property grounds
Interior
Exterior
Dining
Exceptional
(7 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
NZ$4,646
for 7 nights, 1 cabin
NZ$664 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
View from ski room to trail thru woods to Grouse Run - fantastic location!!
Spring at Jiminy Peak 2019
Country Inn heated pool & outdoor hot tub is open all year.  Towels are provided
Night skiing view from living room
Exceptional
(46 reviews)

Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.

Hancock

12% off
NZ$9,532
for 7 nights, 1 home
NZ$1,362 per night
includes taxes & fees
Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
Interior
Interior
Living area
Room
Exceptional
(40 reviews)

A MAGIC SPOT: Booking all year. The perfect spring/summer mountaintop location.

Stephentown

8% off
NZ$2,876
for 7 nights, 1 home
NZ$411 per night
includes taxes & fees
A MAGIC SPOT: Booking all year. The perfect spring/summer mountaintop location.
Front Gardens
Living Room
Property grounds
Back Porch
Exceptional
(27 reviews)

Secluded Family Home in Serene Stockbridge Woods

South Lee

8% off
NZ$5,368
for 7 nights, 1 home
NZ$767 per night
includes taxes & fees
Secluded Family Home in Serene Stockbridge Woods
Property grounds
Interior
Kitchen
Interior
Excellent
(14 reviews)

Canary Lodge - Berkshires Mountain Retreat - 6 Guests

West Stockbridge

8% off
NZ$6,593
for 7 nights, 1 home
NZ$942 per night
includes taxes & fees
Canary Lodge - Berkshires Mountain Retreat - 6 Guests
The Country Store
The Deck at Christiansen's Tavern
Outdoor dining
Outdoor Pool near The Country Store
Exceptional
(25 reviews)

Five-Star Family Friendly Townhouse in the Heart of Jiminy Peak

Hancock

8% off
NZ$8,856
for 7 nights, 1 home
NZ$1,265 per night
includes taxes & fees
Five-Star Family Friendly Townhouse in the Heart of Jiminy Peak
Room
Interior
Interior
Bathroom
Exceptional
(6 reviews)

Historic Stone Church in The Berkshires

Lanesborough

8% off
NZ$4,715
for 7 nights, 1 home
NZ$674 per night
includes taxes & fees
Historic Stone Church in The Berkshires
another view of kitchen
new backyard table
another view of same bedroom as well as makeup table
kitchen and laundry room area
Exceptional
(17 reviews)

3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY

Lanesborough

22% off
NZ$6,160
for 7 nights, 1 apartment
NZ$880 per night
includes taxes & fees
3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
Gorgeous open concept living room
Private kitchen
Custom Chef's Kitchen with high end appliances from Bertazzoni and Fisher & Paykel
Quarter & Rift sawn white oak floors
Exceptional
(11 reviews)

The Penthouse, Downtown Lenox by Evergreen Home

Lenox

11% off
NZ$7,994
for 7 nights, 1 apartment
NZ$1,142 per night
includes taxes & fees
The Penthouse, Downtown Lenox by Evergreen Home
Large Smart HDTV with electric fireplace in living room, showing dining room
View from 2nd floor balcony (after leaves have fallen)
Entrance into house with wood burning stove to right and staircase
Smart TV in Downstairs room with view of entrance to house and doors to room
Exceptional
(72 reviews)

2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

Williamstown

12% off
NZ$4,308
for 7 nights, 1 home
NZ$615 per night
includes taxes & fees
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
  • Peace of mind

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  • More quality time

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Historical New Lebanon will entice you

Enjoy the history and other features of New Lebanon. This city is well-known for its restaurants and shopping. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in New Lebanon

Are you hoping to discover attractions to see in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes New Lebanon a fun spot to go on holiday. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Bousquet Ski Area (6.9 mi / 11.1 km)
  • Jiminy Peak Mountain Resort (8.3 mi / 13.3 km)
  • Wyndhurst Golf & Club (10.7 mi / 17.2 km)
  • Waubeeka Golf Links (15.5 mi / 25 km)
  • Furnace Brook Winery at Hilltop Orchards (4.8 mi / 7.8 km)
  • Kennedy Park (8.5 mi / 13.6 km)

Exploring the natural landscape of New Lebanon

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in New Lebanon. These are some of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Queechy Lake (4 mi / 6.5 km)
  • Stockbridge Bowl (9.8 mi / 15.7 km)
  • The Mount (10.6 mi / 17.1 km)
  • Mount Greylock State Reservation Visitor Center (11.2 mi / 18 km)
  • Berkshire Botanical Garden (11.7 mi / 18.8 km)
  • Naumkeag Museum (12.8 mi / 20.5 km)

Travelling to and around New Lebanon

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 6 mi (9.7 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Hudson, NY (HCC-Columbia County), which is 19.9 mi (32.1 km) away.

Frequently asked questions

What is the best area to stay in New Lebanon when booking a holiday home?
If you're thinking of a getaway to New Lebanon, Lebanon Springs is one of the most desirable neighbourhoods to stay. Whether you opt for a cottage, condo or different type of property, you'll always have the entire place to yourself.
What is the most popular type of holiday home accommodation in New Lebanon?
According to our data, houses are the most desirable holiday property type in New Lebanon. But of course, everyone's idea of the perfect trip isn't the same. Bookabach has holiday homes of all sizes and shapes, and we'll help you to find the perfect fit.
How much does it cost to rent a holiday home in New Lebanon?
A number of factors determine how much you'll pay for a holiday home in New Lebanon, such as the time of year, property type and length of stay. Still, all Bookabach homes have something in common — incredible value. Just enter your travel dates to find your ideal fit.
How much does it cost to rent a beach house in New Lebanon?
Prices for beach houses in New Lebanon can differ depending on the size and style of the property and when you're travelling. All you have to do is enter your travel dates into Bookabach and the number of guests to see available options and prices. From there you can use our filters to narrow down your search by ratings, amenities, nearby activities and more.
Are there pet-friendly holiday homes in New Lebanon?
Pack a travel bag for your beloved pooch because New Lebanon has seven stays that open their doors to pets. Let your happy hound join in with the family fun at one of our pet-friendly holiday homes on Bookabach. Simply enter your dates then check the "Pets allowed" filter box.
What are popular home amenities in New Lebanon?
Some of the most popular home amenities people are searching for in New Lebanon include nearby museums, an electric car charging station and a firepit. Whether you're travelling with pals, family or even pets, Bookabach holiday homes provide the best amenities for chilling out with the people you cherish the most.
Are there large group holiday homes in New Lebanon?
With four New Lebanon holiday homes that can host five or more people, you can invite a few extra family members or pals along. Whether you're planning an informal gathering or a birthday party, Bookabach will help you find the ideal space to match the occasion.
Are there holiday homes in New Lebanon that welcome kids?
With seven family-friendly holiday homes to choose from in New Lebanon, now is a fantastic time to introduce your kids to the wonders of travel. Simply check our "Properties good for families" filter to locate stays that come with amenities ideal for travelling families, like full kitchens, outdoor spaces, entertainment areas and hot tubs.
What are the top attractions for families in New Lebanon?
If you're holidaying with the kids, make sure you put these family-friendly attractions in New Lebanon on your list of things to see:
  • Mount Lebanon Shaker Village
  • New Lebanon Library
Can I find two-bedroom holiday homes in New Lebanon?
You can pick from two two-bedroom properties in New Lebanon. Settle the kids into the second room or fill it with a couple of your favourite people. There's space for whoever's lucky enough to be joining your adventure.
Are there holiday homes with WiFi in New Lebanon?
You'll find three holiday homes with WiFi in New Lebanon. If you'd like to disconnect from daily life while on holiday, but still want to be connected to the internet, these getaways have just what you need. Narrow your search by applying the WiFi filter on Bookabach.
How can I find holiday homes with air conditioning in New Lebanon?
Decide on your travel dates and then use the filter tool to view holiday homes with air conditioning in New Lebanon on Bookabach. With five air-conditioned properties to choose from here, you can look forward to a cool and comfy break.
How old do you have to be to rent a holiday home in New Lebanon?
The minimum age allowed can differ between properties on Bookabach, so be sure to look at the rules of the holiday home in New Lebanon you want to book. But typically, it's 16, 18 or 21.
How long can I rent a holiday home in New Lebanon for?
How long you can book a holiday home in New Lebanon is up to the property. Just enter your preferred dates to display a list of options offering extended stays. With a range of features like air conditioning and full kitchens, as well as some offering discounted weekly or monthly prices, you're sure to get the perfect place to call your home away from home in New Lebanon.