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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, 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!

Top guest favorite
An A-frame cabin is nestled within a forested area, featuring a striking black exterior and a sloping roof with wooden accents. Tall grasses and shrubs surround the entrance, creating a natural backdrop. A gravel path leads to the cabin, framed by lush greenery.
Cabin in Saugerties
4.97 out of 5 average rating, 165 reviews

Luxury A-Frame Cabin in the Woods with Sauna

🔨 Heads up: We’re currently making improvements to the property and there’s a chance of construction activity nearby on weekdays between 8am–4pm for the next few months. Evenings, nights, and weekends are completely peaceful and unaffected. 🏡 Modern A-frame in the Catskills with woodland views. Cedar barrel sauna, outdoor shower, smokeless fire table, and wrap-around deck. Queen bedroom with forest views, outdoor fireplace, fast Wi-Fi. Minutes to trailheads, waterfalls, and farmers markets.

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, 184 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.

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
4.91 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.

Top guest favorite
Home in Lee
4.99 out of 5 average rating, 312 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.

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 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.

Top guest favorite
Home in Lebanon Springs
5 out of 5 average rating, 20 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.

Top guest favorite
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, 322 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.

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!

Top guest favorite
Home in Pittsfield
5 out of 5 average rating, 31 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. 

Top guest favorite
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, 368 reviews

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

Blush at Art Park Homes is a romantic boutique tiny home getaway in Chatham, NY—just 2.5 hrs from NYC & Boston. 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

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

Summer Mountain Retreat + Views, Fire Pit, Hot Tub

Escape to your modern mountain retreat—perfect for Summer getaways! Just 15 mins to Tanglewood, MASS MoCA & The Clark, and close to scenic hikes, waterfalls, farm stands, breweries, and charming small towns. Soak in the wood-fired hot tub, enjoy evenings around the Breeo fire pit, cook fresh seasonal meals, and unwind in peaceful privacy. With EV charging and a quiet workspace, it’s ideal for refreshing escapes or Summer adventures.

Popular amenities for New Lebanon vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great vacation rentals in New Lebanon

Guest favorite
Two white Adirondack chairs are positioned on a grassy slope, facing a vibrant sunset over distant mountain silhouettes. The warm hues of the setting sun create a serene backdrop, with trees framing the scene and a peaceful atmosphere enveloping the area.
Chalet in Canaan
4.9 out of 5 average rating, 21 reviews

Sunset Ridge Chalet•Berkshires• Queechy Lake•HRV

A spacious living area displays exposed wooden beams, complemented by large windows allowing natural light. A cozy seating arrangement includes a sofa and wooden chairs, while a decorative rug enhances the ambiance. A striking spiral staircase leads to the upper level, adding architectural interest.
Home in New Lebanon
4.67 out of 5 average rating, 18 reviews

Historic New Lebanon Hideaway on 33 Private Acres!

Guest favorite
The cozy cabin, constructed from natural wood, is surrounded by lush greenery and colorful flower beds. An inviting front porch is framed by railing and steps. Two windows and a door create a symmetrical facade, while a serene landscape enhances the cabin's rural charm.
Cabin in East Nassau
4.94 out of 5 average rating, 51 reviews

The Kinderhook Cabin on the Kinderhook creek.

Top guest favorite
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

Guest favorite
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, 143 reviews

Cozy Berkshire Hills Escape | Near Tanglewood

Top guest favorite
Home in East Jewett
5 out of 5 average rating, 17 reviews

Creekside Couple's Escape w/ Hot Tub Sauna & More!

Top guest favorite
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, 83 reviews

Historic Stone Church in The Berkshires

Guest favorite
Guesthouse in Canaan
5 out of 5 average rating, 12 reviews

Berkshires Retreat: Treetop Guest House + Gardens

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