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Vacation rentals in New Lebanon

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Top-rated vacation rentals in New Lebanon

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

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Guest favorite
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
4.95 out of 5 average rating, 277 reviews

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!

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Top guest favorite
Cabin in East Nassau
4.97 out of 5 average rating, 109 reviews

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!

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Top guest favorite
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
4.99 out of 5 average rating, 120 reviews

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!

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Guest favorite
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
4.91 out of 5 average rating, 187 reviews

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.

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Guest favorite
A well-appointed bedroom features a spacious bed with a solid headboard and neutral bedding. Two bedside lamps provide soft lighting, casting a warm glow. Wooden paneling complements the carpeted floor, creating a cozy atmosphere in the loft suite.
Farm stay in New Lebanon
4.89 out of 5 average rating, 81 reviews

NEW RENO - Chalet-style farm loft near Tanglewood

Welcome to Shaker Meadows, a historic 18th century Berkshires farm. This newly renovated chalet-style loft in the farm’s 1940s creamery has a full kitchen, & deck looking out onto the Berkshire mountains. Explore winding paths around 50 acres of farmland & hills or drive 10 mins to Hancock Shaker Village, 15 mins to Tanglewood/Jiminy Peak—a wonderful base for exploring the art, music, and history of the Berkshires. Great for couples, families, & solo adventurers. Kid- and pet-friendly.

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Guest favorite
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
4.97 out of 5 average rating, 33 reviews

Bucolic Pet Friendly Oasis | 10 min to Tanglewood

Escape to our peaceful retreat on 5 private acres. Large picture windows envelope you in the gorgeous surroundings, and the tree lined property creates a sense of utter tranquility. Bask in the breeze on the sun porch, curl up by the wood burning stove, or enjoy a lounge on the deck. Centrally located in the Berkshires: ⭐️ 10 minutes to Tanglewood/Lenox ⭐️ 7 minutes from West Stockbridge/ I-90 ⭐️ 20 minutes to Great Barrington, Stockbridge & Pittsfield Enjoy our oasis all year r

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Top guest favorite
A red brick cottage is set against a backdrop of lush green grass and trees. The home features a gabled roof and large windows. A small, decorative arbor with climbing plants stands in the foreground, providing an inviting entrance to the property.
Home in Canaan
4.97 out of 5 average rating, 91 reviews

Crossings Cottage

Welcome to Crossings Cottage! Conveniently located in the heart of the bucolic Berkshires right on the Massachusetts, New York State line. This beautiful property sits tucked down a country road just 1 mile from the Mass Pike and New York State Thruway, making it very easy to access. The Cottage sits on 50+ acres with panoramic views of the property off the back deck. Its location is only 8 miles from Tanglewood, Lenox, and Stockbridge! Home Range Winery is only a 5 minute walk!

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Top guest favorite
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
5.0 out of 5 average rating, 37 reviews

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.

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Top guest favorite
Home in New Lebanon
5.0 out of 5 average rating, 27 reviews

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.

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Top guest favorite
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
5.0 out of 5 average rating, 19 reviews

Mountain View Getaway

Relax with the whole family at this peaceful place to stay. Enjoy beautiful views of Pittsfield State Forest. Super close to Tanglewood, the Berkshires, Jiminy Peak, Balderdash Winery, Ramblewild, Queechy Lake, Shaker Ridge Trails, Williams College, and much more. The house is on 2 1/2 acres. It is a charming, cozy, and welcoming home with plenty of outdoor space. Families will love sitting by the fire pit and roasting marshmallows. Dogs are welcome for a small fee.

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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
4.87 out of 5 average rating, 61 reviews

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!

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Top guest favorite
Home in Pittsfield
5.0 out of 5 average rating, 37 reviews

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. 

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Popular amenities for New Lebanon vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great vacation rentals in New Lebanon

Top guest favorite
A spacious front porch features several wooden rocking chairs and a swing, positioned against stone columns. The floor is lined with wooden planks, and greenery is visible in the background. Sunlight filters through the trees, creating a serene outdoor seating area.
Home in Old Chatham
5.0 out of 5 average rating, 35 reviews

Monk's Bunk, Old Chatham

LocationFamilyOutdoor spaces

A 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
4.84 out of 5 average rating, 149 reviews

Cozy Berkshire Hills Escape | Near Tanglewood

LocationFamilyQuiet

Top guest favorite
A view of the cottage is framed by lush greenery and trees. The vibrant red exterior of the cottage contrasts against the surrounding open fields. A grassy area with a small seating arrangement is visible, inviting relaxation amidst nature.
Guesthouse in Canaan
4.93 out of 5 average rating, 220 reviews

Airy cottage with meadow views in The Berkshires

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Guest favorite
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
5.0 out of 5 average rating, 24 reviews

The Spencer House 7 Bedroom Berkshire Inn

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Guest favorite
Guesthouse in Canaan
4.94 out of 5 average rating, 16 reviews

Berkshires Retreat: Treetop Guest House + Gardens

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Top guest favorite
Home in New Lebanon
5.0 out of 5 average rating, 7 reviews

Spring Hill Cottage in New Lebanon

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Top guest favorite
Home in New Lebanon
5.0 out of 5 average rating, 10 reviews

Above the Clouds Mountain Retreat

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Top guest favorite
Home in Canaan
4.95 out of 5 average rating, 44 reviews

Secluded Mountain and Lake View in Canaan, NY

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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