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Holiday houses 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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Top Guest favourite
A tiny home features a private hot tub on the deck, illuminated by soft LED lights. The structure is surrounded by natural wood paneling, with doors leading into the cozy interior, where warm light spills out, creating an inviting ambiance.
Tiny home in Chatham
4.99 out of 5 average rating, 371 reviews

Boutique TINY home+private HOT TUB-walk to Main St

Sept. SPECIAL(Mon-Thurs): Includes Prosecco, s’mores kit, firepit supplies. Blush is a romantic boutique tiny home getaway in Chatham, NY—just 2.5 hrs from NYC. Enjoy a private hot tub, firepit, dreamy loft lounge, plush queen bed, full kitchen & curated luxe design throughout. Tucked into a peaceful private oasis, yet only a 2-min walk to Main St. restaurants, brewery, shops & theater. Perfect for couples seeking a unique Hudson Valley getaway near hiking, galleries, great dining. @artparkhomes

LocationFamilyIndoor spaces

Top Guest favourite
A striking octagonal home is illuminated at dusk, showcasing wrap-around glass windows that blend with the surrounding woodland. The exterior features natural stone accents, and a warm glow from a light at the entrance creates a welcoming ambiance amidst a snowy landscape.
Chalet in Otis
4.95 out of 5 average rating, 480 reviews

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

ValueFamilyHiking

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
4.95 out of 5 average rating, 273 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!

LocationFamilyOutdoor spaces

Guest favourite
Cabin in East Nassau
4.97 out of 5 average rating, 101 reviews

Luxury Cabin - Fall Foliage & 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 and chairs, Webber Grill, radiant floor, WFH space, and EV charging!

LocationFamilyOutdoor spaces

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
4.91 out of 5 average rating, 186 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.

LocationFamilyDecor

Guest favourite
An open living space features a large sectional sofa surrounding a central glass coffee table. A decorative chandelier hangs from the exposed wooden beams. Natural light streams in through multiple floor-to-ceiling windows, revealing views of the surrounding greenery.
Barn in East Chatham
4.96 out of 5 average rating, 111 reviews

Luxury Barn Retreat Near Hudson & the Berkshires

Set on eight private acres where New York meets the Berkshires, this architect-designed retreat combines dramatic contemporary design with warmth and comfort. Soaring ceilings, a chef’s kitchen, designer interiors, peaceful outdoor spaces and nearby lake access create the perfect escape. Ideal for couples, families with children or close friends, it’s a short drive from Hudson, Chatham, Great Barrington, Tanglewood and countless other destinations for shopping, dining, hiking and more.

FamilyValueHospitality

Guest favourite
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
4.91 out of 5 average rating, 70 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.

FamilyValueKitchen

Top Guest favourite
Home in Lee
4.99 out of 5 average rating, 313 reviews

Berkshire Mountain retreat with Urban eco-luxuries

600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relaxing our wood-fired hot tub- we hope you enjoy your stay and will visit us again.

LocationFamilyCondition

Top Guest favourite
Home in Lebanon Springs
5 out of 5 average rating, 23 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.

ValueFamilyCleanliness

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
4.99 out of 5 average rating, 326 reviews

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.

LocationValueSolo travel

Guest favourite
Tiny home in New Marlborough
4.94 out of 5 average rating, 190 reviews

Bedroom Forest View I Sauna I Fire-pit I Trails

Escape to a secluded custom built tiny house nestled amongst old pines and the Umpachene River. Inside, rustic charm meets modern comfort with 2 lux queen-sized beds, a well-equipped kitchen and bathroom, a massive bedroom forest view and a private sauna. Outside the home you can find a cozy fire-pit, trails that lead down to the river, and a dining table for all your meals. Go out for a day of hiking and exploring, and come back to unwind to sounds of nature.

ValueFamilyBackyard

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, 60 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!

FamilyValueShared spaces

Popular amenities for New Lebanon holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in New Lebanon

Top Guest favourite
An outdoor scene features a clear blue sky above a heated saltwater pool set within a spacious green yard. Surrounding trees provide a natural backdrop, and a small shed is visible next to the pool, which is enclosed by a wooden fence.
Home in New Lebanon
4.99 out of 5 average rating, 70 reviews

Berkshire Mountain home views, pool, Queechy Lake

FamilyLocationKitchen

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
5 out of 5 average rating, 37 reviews

20 minutes to Tanglewood

LocationFamilyHospitality

Guest favourite
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 Lebanon Springs
4.85 out of 5 average rating, 144 reviews

Cozy Berkshire Hills Escape | Near Tanglewood

ValueFamilyAccuracy

Top Guest favourite
The historic stone church exterior is framed by lush greenery and a manicured lawn. Towering above, the bell tower features intricate architectural details. A wooden fence surrounds the property, leading to a pathway that invites exploration of the beautiful grounds.
Home in Lanesborough
4.98 out of 5 average rating, 86 reviews

Historic Stone Church in The Berkshires

FamilyValueAccuracy

Guest favourite
Guesthouse in Canaan
5 out of 5 average rating, 13 reviews

Berkshires Retreat: Treetop Guest House + Gardens

FamilyLocationBeach

Guest favourite
Home in New Lebanon
5 out of 5 average rating, 6 reviews

Above the Clouds Mountain Retreat

LocationFamilyView

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
5 out of 5 average rating, 16 reviews

Mountain View Getaway

LocationFamilyParking

Guest favourite
Earthen home in Canaan
5 out of 5 average rating, 10 reviews

Guest Eco Studio w/ Pool & Sauna on 100+ Acres

LocationPoolHospitality

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