New Lebanon holiday rentals

We found 458 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:6 Nov - 13 Nov

Dining room with butcher block table
Terrace/patio
Property grounds
Screened in porch
Exceptional
(101 reviews)

Vacation in a Berkshire Farmhouse

West Stockbridge

8% off
AU$3,790
for 7 nights, 1 home
AU$541 per night
includes taxes & fees
Vacation in a Berkshire Farmhouse
Dining
Private kitchen
Private kitchen
Interior
Exceptional
(5 reviews)

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

Williamstown

20% off
AU$2,916
for 7 nights, 1 room
AU$417 per night
includes taxes & fees
Dog Friendly Country Farmhouse, 2 bed / 2 bath; 1.5 miles from Jiminy Peak
Enclosed porch- view into back yard- dining/game table
Kitchen with counter seating for 4- door on the right to garage
Outdoor dining
Property grounds
Exceptional
(9 reviews)

Sophisticated Lenox Retreat by Evergreen Home

Lenox

11% off
AU$5,404
for 7 nights, 1 home
AU$772 per night
includes taxes & fees
Sophisticated Lenox Retreat by Evergreen Home
Kitchen with stainless steel appliances
Fully screened porch!
Front Staircase
Dining Room w/ Doors to Screened Porch Dining Area
Exceptional
(7 reviews)

Berkshires Colonial on 2 Acres by Evergreen Home

Richmond

12% off
AU$5,399
for 7 nights, 1 home
AU$771 per night
includes taxes & fees
Berkshires Colonial on 2 Acres by Evergreen Home
Interior
Living area
Interior
Exterior detail
Exceptional
(35 reviews)

Renovated Pittsfield Colonial by Evergreen Home

Pittsfield

11% off
AU$6,002
for 7 nights, 1 home
AU$857 per night
includes taxes & fees
Renovated Pittsfield Colonial by Evergreen Home
View from the lawn by the water
view from the 2nd bedroom
Workstation with a view!
Open plan dining area with water views and access to the sunroom
Exceptional
(65 reviews)

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield

8% off
AU$6,908
for 7 nights, 1 home
AU$987 per night
includes taxes & fees
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Interior
Property grounds
Exterior
Interior
Exceptional
(10 reviews)

Mountain View Retreat in Hudson Valley near Berkshire Attractions

Old Chatham

8% off
AU$2,584
for 7 nights, 1 cottage
AU$369 per night
includes taxes & fees
Mountain View Retreat in Hudson Valley near Berkshire Attractions
Living area
Interior
Dining
Exterior
Exceptional
(7 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
AU$3,849
for 7 nights, 1 cabin
AU$550 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
Country Inn heated pool & outdoor hot tub is open all year.  Towels are provided
Spring at Jiminy Peak 2019
View from ski room to trail thru woods to Grouse Run - fantastic location!!
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
AU$7,869
for 7 nights, 1 home
AU$1,124 per night
includes taxes & fees
Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
Exterior
Interior
Living area
Interior
Exceptional
(40 reviews)

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

Stephentown

8% off
AU$2,426
for 7 nights, 1 home
AU$347 per night
includes taxes & fees
A MAGIC SPOT: Booking all year. The perfect spring/summer mountaintop location.
Kitchen
Living Room
Property grounds
Back Porch
Exceptional
(27 reviews)

Secluded Family Home in Serene Stockbridge Woods

South Lee

8% off
AU$4,409
for 7 nights, 1 home
AU$630 per night
includes taxes & fees
Secluded Family Home in Serene Stockbridge Woods
Kitchen
Interior
Interior
Kitchen
Excellent
(14 reviews)

Canary Lodge - Berkshires Mountain Retreat - 6 Guests

West Stockbridge

8% off
AU$5,453
for 7 nights, 1 home
AU$779 per night
includes taxes & fees
Canary Lodge - Berkshires Mountain Retreat - 6 Guests
The Country Store
The Deck at Christiansen's Tavern
Outdoor Pool near The Country Store
Outdoor dining
Exceptional
(24 reviews)

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

Hancock

8% off
AU$7,308
for 7 nights, 1 home
AU$1,044 per night
includes taxes & fees
Five-Star Family Friendly Townhouse in the Heart of Jiminy Peak
50 inch TV for family movie night!
BBQ dinner not included :)
Exterior
Interior
Exceptional
(10 reviews)

Family Fun in The Berkshires at Beautiful Hygge House

Richmond

8% off
AU$5,161
for 7 nights, 1 home
AU$737 per night
includes taxes & fees
Family Fun in The Berkshires at Beautiful Hygge House
Bathroom
Interior
Interior
Room
Exceptional
(6 reviews)

Historic Stone Church in The Berkshires

Lanesborough

8% off
AU$3,869
for 7 nights, 1 home
AU$553 per night
includes taxes & fees
Historic Stone Church in The Berkshires
Interior
Dining
Entry and living room
Living Room, wow!
Exceptional
(14 reviews)

New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.

Richmond

17% off
AU$3,554
for 7 nights, 1 apartment
AU$508 per night
includes taxes & fees
New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.
Beaver Pond Pool/clubhouse
new backyard table
kitchen and laundry room area
another view of same bedroom as well as makeup table
Exceptional
(17 reviews)

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

Lanesborough

23% off
AU$5,091
for 7 nights, 1 apartment
AU$727 per night
includes taxes & fees
3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
Custom Chef's Kitchen with high end appliances from Bertazzoni and Fisher & Paykel
Private kitchen
Quarter & Rift sawn white oak floors
Gorgeous open concept living room
Exceptional
(11 reviews)

The Penthouse, Downtown Lenox by Evergreen Home

Lenox

11% off
AU$6,432
for 7 nights, 1 apartment
AU$919 per night
includes taxes & fees
The Penthouse, Downtown Lenox by Evergreen Home
Views from the back of the 16 acres on the property
View from 2nd floor balcony (after leaves have fallen)
Smart TV in Downstairs room with view of entrance to house and doors to room
Entrance into house with wood burning stove to right and staircase
Exceptional
(72 reviews)

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

Williamstown

12% off
AU$3,380
for 7 nights, 1 home
AU$483 per night
includes taxes & fees
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • 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)
  • Kennedy Park (8.5 mi / 13.6 km)
  • Wyndhurst Golf & Club (10.7 mi / 17.2 km)
  • Furnace Brook Winery at Hilltop Orchards (4.8 mi / 7.8 km)
  • Waubeeka Golf Links (15.5 mi / 25 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)
  • Kennedy Park (8.5 mi / 13.6 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)

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. Stayz 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 Stayz 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 Stayz 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 Stayz. 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, Stayz 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, Stayz 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 Stayz.
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 Stayz. 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 Stayz, 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.

More holiday ideas