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Holiday rentals in New Lebanon

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Top-rated holiday rentals in New Lebanon

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
An open living space with a high wood-beam ceiling is displayed. A large stone fireplace serves as a focal point, surrounded by comfortable seating. A kitchen island with stools offers additional space. Large windows allow natural light to fill the room, enhancing the inviting atmosphere.
Farm stay in New Lebanon

Barn Stay at Shadowbrook Farm

Welcome to the Shadowbrook Farm Stay. Tucked in the hills of upstate New York, this 1700's Shaker barn has been restored into a beautiful guest house. It sits upon a two hundred acre working pasture raised meat farm. This barn was used to hold, and milk cows for two hundred and fifty years. Guests will have access to portions of the farm lands which are highlighted on the maps provided in the Farm Stay manual. If you follow the farm road, you are able to meet every farm animal on the property!

4.95 out of 5 average rating, 277 reviews
Top guest favourite
Cabin in East Nassau

Fall Foliage Luxury Cabin & View Autumn Adventures

Welcome to our mountain retreat, nestled in the heart of nature and brought to you by Den Outdoors. 25 mins to Tanglewood, 35 mins to Jacobs Pillow, 15 mins to Jiminy Peak, 30 mins to The Clark, MASS MoCA, and the Berkshire region. 10 mins to a swimmable lake. 2.5 hrs from NYC and from Boston. Come experience all Autumn has to offer! Stunning views, no visible neighbors, Goodland wood fired hot tub, Breeo Fire pit, large Webber Grill, radiant floor, EV charging, and the MOST STUNNING view!

4.97 out of 5 average rating, 110 reviews
Guest favourite
A white building with a dark roof is set amidst vibrant fall foliage. Golden and orange leaves decorate the trees in the background, while a gravel path leads to the entrance. A bench is positioned in front of the building, inviting relaxation.
Farm stay in New Lebanon

1800s Carriage house in Berkshires / Hudson Valley

The carriage house was built in the 1800s on this Shaker farm. We've renovated it to provide modern convenience (minisplit HVAC, high speed wifi) and reviving original wood floors & antique furniture (from when it was an antique shop in the 1940s). This cozy spot is an ideal location for exploring the Berkshires & Hudson River Valley. 15-40min away from everything you want to do: Tanglewood concerts, plays, museums, hikes, lakes, skiing, wineries/breweries, farms, autumn leaves, historic sites.

4.91 out of 5 average rating, 75 reviews
Top guest favourite
The charming exterior of a renovated farmhouse features a spacious front porch with a red bench and hanging flower baskets. Large windows allow natural light to fill the entryway, while lush green grass and trees frame the property.
Home in Canaan

NEW! Berkshires Farmhouse w/ Firepit & Wood Stove

Welcome to our little slice of heaven upstate. Located just a 5-minute drive to the MA border, a stay at our home in Canaan, NY means access to the best of both Columbia County and the Berkshires. In the summer, enjoy the private Adams Point Beach on Queechy Lake and easy access to Tanglewood. In the winter, explore 4 different local ski resorts and curl up by the cozy wood stove. In between, enjoy the peaceful pond views and secluded location on a dirt road. We can't wait to welcome you!

4.99 out of 5 average rating, 121 reviews
Guest favourite
A wrap-around porch features a small table with two colorful chairs, overlooking a serene lake framed by lush trees and greenery. The view showcases calm water, complemented by distant hills under a clear blue sky.
Home in Canaan

Berkshire Lakefront House with Amazing Views

Enjoy the culture of the Berkshires & Hudson - 15 min from Tanglewood, Norman Rockwell Museum, Shakespeare & Co, PS21, McHaydn Theatre, Mount Greylock, Jiminy Peak Resort, zipline parks, Bousquet & more. Restaurants & market within driving distance and a membership-only beach within a short walk or drive. Great lake views with wrap-around porch. The lake is family-friendly. We welcome couples, solo adventurers, and families. Sorry, no "Group Bookings" - book & pay via one account only.

4.91 out of 5 average rating, 187 reviews
Top guest favourite
A kitchen features light blue cabinetry and a central island with a granite countertop. Above the island, open shelving displays decorative bowls and glassware. A dining table with wooden chairs is positioned nearby, while a cozy seating area is visible in the background.
Place to stay in New Lebanon

20 minutes to Tanglewood

This property is like nothing you've ever seen--a gem near the top of Mt. Lebanon with 75 acres of forest, streams, waterfalls, gardens, and historic ruins on a former Shaker settlement. The newly renovated Caretaker's Cottage has 2 bedrooms, kitchen, living room, and bathroom. The Taconic and Berkshire mountains stretch out before the deck and screened-in porch. Berkshire and Hudson Valley restaurants, shops, and entertainment are all nearby. Owners on site if you need them.

5.0 out of 5 average rating, 37 reviews
Top guest favourite
Home in New Lebanon

Modernized 1860s Getaway w/ Queechy Lake Passes*

Unwind in our quiet, spacious, light-filled, rural home without leaving modern conveniences behind. Located in Historic Lebanon Springs, our newly restored antique home is near both Hudson Valley restaurants and shops and the Berkshire's vast outdoor activities. We took great care to save this home's historic details while creating a fully modernized, comfortable retreat. Every room is thoughtfully curated with local antiques, artwork, and many unique touches you'll enjoy.

5.0 out of 5 average rating, 27 reviews
Top guest favourite
A cozy living area features a plush sofa paired with two comfortable chairs. A round coffee table rests at the center. Large windows allow for natural light, framing views of the outdoors. A vibrant wall art piece adds a touch of color to the neutral decor.
Guest house in Canaan

New-Modern Guesthouse

Tucked away on 10 peaceful acres in the Berkshires/Hudson Valley, our guesthouse is a cozy, design-forward escape surrounded by nature. Sip coffee on the deck or curl up with views of pastures and woods. In autumn, enjoy brilliant foliage and crisp air. In winter sleep in and relax or head to Jiminy Peak or Bousquet for skiing, snowshoe nearby trails, or explore Lenox, Chatham, and Great Barrington. A perfect setting to rest, recharge, and savor the beauty of the season.

5.0 out of 5 average rating, 40 reviews
Top guest favourite
A two-story home is depicted, featuring a grey wooden exterior with multiple windows. A wooden deck with stairs leads to the entrance, surrounded by green grass and vibrant yellow flowers. The clear blue sky complements the inviting structure.
Farm stay in Pittsfield

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or just relax out on the balcony and take in the views.

4.99 out of 5 average rating, 339 reviews
Superhost
An open living space features a spacious bed and seating area, highlighted by natural light from multiple windows. A ceiling fan is present, and modern furnishings are arranged thoughtfully. Light wood flooring complements the neutral tones of the decor, creating a serene atmosphere.
Home in New Lebanon

Ridgeview Retreat | Valley Views • Sleeps 6

Welcome to your perfect getaway in New Lebanon! This open and spacious home offers stunning views of the New Lebanon Valley. Enjoy modern amenities throughout, ensuring a comfortable and enjoyable experience. Just a short drive away, you’ll find skiing adventures at Jiminy Peak and the enchanting ruins at Sassafras Farm, perfect for exploration. Unwind and reconnect with nature in this inviting retreat—your ideal home base for adventure and relaxation awaits!

4.87 out of 5 average rating, 61 reviews
Top guest favourite
Home in Pittsfield

Cozy cottage on peaceful pond

This little slice of heaven is located on the serene Richmond Pond. Right down the street from Balderdash winery and a 15 minute drive to charming downtown Lenox and Tanglewood. In Lenox you can find great dining, shopping, and there is plenty of hiking and biking around this area. This cozy cottage has everything you need for a Berkshire retreat. In the fall cozy up next to the fireplace inside or out take a break and unwind at this Peaceful oasis. 

5.0 out of 5 average rating, 38 reviews
Superhost
A two-story duplex is surrounded by greenery, showcasing a wooden deck with latticework. The exterior is clad in light-colored siding, with green shutters adorning the windows. A landscaped yard features various plants, and a road is visible in the background.
Flat in Canaan

Comfy - Country Family Home- Affordable

Book now!! The fall is approaching. Come enjoy the easy restful place in the Berkshires, Columbia County. We are close to apple picking and hiking, or enjoying the turning of the leaves. Quaint one bedroom duplex in the center of our little town. Shop and dine in Chatham, Lenox, Stockbridge, Great Barrington, Woodstock, Saratoga, or grill on the deck.

4.84 out of 5 average rating, 117 reviews

Popular amenities for New Lebanon holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in New Lebanon

Guest favourite
A spacious house is surrounded by tall trees, showcasing a blend of gray siding and large windows. Lush greenery and ornamental grasses frame the property, while a cozy outdoor barrel sauna and a patio umbrella add inviting touches to the serene landscape.
Home in Canaan

The Little Yellow Door

4.96 out of 5 average rating, 53 reviews
Top guest favourite
A covered porch featuring wooden flooring and a ceiling of natural wood. Two wooden chairs with striped cushions are positioned beside a small table. A rug adds texture, while expansive windows allow views of the outdoor greenery.
Home in New Lebanon

Mountain View Getaway

5.0 out of 5 average rating, 19 reviews
Guest favourite
A charming cottage is nestled among lush greenery, featuring a welcoming front porch with decorative railings. Flower pots line the entrance, adding a touch of color. A white picket fence surrounds the property, offering a sense of privacy and connection to nature.
Cottage in Malden Bridge

Cozy, charming cottage by the creek w/2 queen beds

4.94 out of 5 average rating, 35 reviews
Guest favourite
A serene landscape is displayed, featuring a red barn and a single-story blue house surrounded by lush green grass. Leafless trees and gentle hills create a peaceful backdrop under a partly cloudy sky.
Home in Richmond

Bucolic Pet Friendly Oasis | 10 min to Tanglewood

4.97 out of 5 average rating, 33 reviewsA covered porch showcases a comfortable seating area with a large umbrella providing shade. A wooden swing hangs on one side, while a cozy couch and chair set invite relaxation. Lush greenery surrounds the deck, creating a serene and private atmosphere.
Home in New Lebanon

Color, Trails + Orchards | Historic Home

4.84 out of 5 average rating, 149 reviews
Guest favourite
A two-story yellow wooden house is surrounded by lush greenery, with a patio area featuring an umbrella and outdoor seating. Flower beds add color to the landscape, and tall trees provide shade. The sunset casts a warm glow over the property.
Home in New Lebanon

The Spencer House 7 Bedroom Berkshire Inn

5.0 out of 5 average rating, 24 reviews
Guest favourite
Guest house in Canaan

Berkshires Retreat: Treetop Guest House + Gardens

4.94 out of 5 average rating, 16 reviews
Top guest favourite
Home in New Lebanon

Above the Clouds Mountain Retreat

5.0 out of 5 average rating, 10 reviews

Frequently Asked Questions

  • What are the best places to stay in New Lebanon?

    Guests commonly stay in countryside cottages, historic farm homes, or rustic cabins that highlight the area's rural charm. Many choose locations near natural scenery, walking trails, or village amenities for added convenience.

  • What are the best things to do in New Lebanon with kids?

    Children often enjoy visiting local farms, exploring interactive exhibits at the Shaker Museum, and hiking family friendly nature trails. Seasonal events and hands-on workshops can provide memorable experiences for all ages.

  • What are some of the best things to do in New Lebanon?

    Explore the Shaker Museum, browse local farm markets, or wander along wooded trails. The region also has art spaces and seasonal fairs reflecting the area's agricultural traditions.

  • How is the weather in New Lebanon?

    New Lebanon experiences cold winters around 16-38°F (-9-3°C) with frequent snow, and warm summers peaking near 82-84°F (28-29°C). Spring and fall bring cooler temperatures and colorful countryside scenery, with rainfall spread throughout the year.

  • When is the best time to visit New Lebanon?

    Late spring through early fall is often recommended for comfortable temperatures between 59-84°F (15-29°C), green landscapes, and outdoor events. Winter brings quieter surroundings and snow, which can be appealing for those interested in a more peaceful visit.

  • What are the best places to visit in New Lebanon?

    Explore the Shaker Museum, wander through rural landscapes, or visit locally rooted farm stands. Historic sites and country roads add to the area's quiet charm.

  • What are some hiking trails in New Lebanon?

    New Lebanon has wooded trails suited to a range of skill levels, with options for both short walks and longer hikes. Visitors often explore routes through forests, near rolling fields, or by gentle streams in the countryside.

  • What are some family activities we can do in New Lebanon?

    Families often enjoy hiking local trails, exploring hands-on exhibits at the Shaker Museum, or picking seasonal produce at area farms. Outdoor picnics and nature walks are popular activities, especially during milder months.

  • What are some of the best day trip ideas from New Lebanon?

    Travelers frequently explore the Berkshires region, scenic state parks, or nearby villages with historic sites and art spaces. Outdoor enthusiasts often seek out local lakes, farm markets, or forested trails in the surrounding countryside.

  • Are there any pet friendly accommodations available in New Lebanon?

    Many accommodations in New Lebanon welcome pets, including cabin rentals and country homes. Check individual listings for specific amenities, outdoor spaces, and pet policies before booking.

  • What are some local tips for visiting New Lebanon?

    Layered clothing is useful, as temperatures can shift quickly in the Berkshires area. Many markets and farms have seasonal schedules, so checking ahead can help with planning, and local trails tend to be less crowded on weekdays.

  • What is New Lebanon known for?

    New Lebanon is known for its Shaker heritage, tranquil countryside, and ties to farming traditions. The area attracts those interested in local history and rural landscapes.

  • What are the best hidden gems to explore in New Lebanon?

    Discover small art studios, tucked-away hiking trails, or family owned farm stands around New Lebanon. Exploring back roads often reveals scenic views and quiet spots for reflection.

  • What are the best foods to try in New Lebanon?

    Farm-to-table cuisine is frequently suggested, with fresh cheeses, seasonal produce, and locally baked bread popular in the area. Travelers also enjoy homemade pies, preserves, and dishes using regional ingredients.

  • What should I bring for a trip to New Lebanon?

    Pack layers to accommodate shifting temperatures, waterproof footwear for trails, and a reusable water bottle for outdoor activities. Insect repellent and sunscreen can be helpful for time spent in natural areas, especially during warmer months.

  • What is the nightlife in New Lebanon like?

    New Lebanon has a relaxed atmosphere, with casual taverns, local bars, and occasional live music at community venues. For a more active nightlife, visitors often head to surrounding towns featuring music halls, breweries, or late-night dining.

  • What are the most popular events or festivals in New Lebanon?

    New Lebanon hosts agricultural fairs and artisan markets, particularly in summer and early fall. Folk music gatherings, seasonal celebrations, and community heritage events are also frequently suggested for visitors.

  • Are there family friendly vacation rentals in New Lebanon?

    New Lebanon has a range of family friendly vacation rentals, such as spacious farmhouses and countryside cottages. Many bookings feature large yards or easy access to outdoor activities that families frequently enjoy.

Destinations to explore