Town of New Lebanon Rentals
From $328 per night (USD)VRBO
Cottage in the Clouds With Mountain Views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Recently renovated 1960's Popular Mechanics kit-home cottage on 63 private acres near the Berkshire's. Enjoy spectacula ...
From $328 per night (USD)VRBO
From $375 per night (USD)Expedia
Restored historic farmhouse on 25 private acres
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
A sunny and spacious farmhouse located in Canaan, NY - at the foot of the Berkshires and the Hudson Valley. This 1870 Sh ...
From $375 per night (USD)Expedia
From $160 per night (USD)VRBO
Near Tanglewood: Historic Summer Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Newly-renovated Berkshire Hills home where rustic charm meets modern elegance. Ideal for families or groups. The open-st ...
From $160 per night (USD)VRBO
From $750 per night (USD)VRBO
Sweeping Mountain Views in the Berkshires
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Mountain views in the Berkshires for every season! Country home in quiet neighborhood on 11 acres surrounded by farms. ...
From $750 per night (USD)VRBO
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A cozy retreat to the farm life.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Welcome to the Shadowbrook Farm Stay. Tucked in the hills of upstate New York, this 1700's Shaker barn has been restored ...
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From $200 per night (USD)VRBO
Hudson River Valley\/Berkshires Rural Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Nice Cape Cod-style home located in the foothills of The Berkshires and just 11 miles northwest of Lenox and Tanglewood. ...
From $200 per night (USD)VRBO
From $400 per night (USD)VRBO
Beautiful 3 BR Berkshire Home - Mountain Views and Privacy on 10 Acres
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful, bright & clean 3 bedroom home is not a 'rental' house (we use it as our family ski house all winter). It sits ...
From $400 per night (USD)VRBO
From $279 per night (USD)VRBO
Berkshires 4br\/2ba, MEMORIAL TO LABOR DAY, '24
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
BERKSHIRES - 4 BR/2BA - Spring &/Or Summer, '24. (Prefer Memorial to Labor Day. PRICE IS BASED ON FULL SEASON RENTAL, BO ...
From $279 per night (USD)VRBO
From $139 per night (USD)VRBO
Historic 1789 Shaker Farmhouse in Berkshires
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 11
Welcome to Shaker Meadows, a historic 18th century Berkshires farm set on 50 acres. The farmhouse has 6 bedrooms, 3 bath ...
From $139 per night (USD)VRBO
From $270 per night (USD)VRBO
Your Dream House: Pine Log Chalet, Sauna, Outdoor Pool
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
This magical very private property, built in 2011 has comfortable sleeping accommodations. The cedar wood sauna and the ...
From $270 per night (USD)VRBO
From $1300 per night (USD)VRBO
Stone Villa: 20 minutes to Tanglewood
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
This property is like nothing you've ever seen. After 2 years of renovation, we welcome you to the Stone Manor --a 150-y ...
From $1300 per night (USD)VRBO
From $350 per night (USD)Expedia
Caretaker's Cottage: 20 minutes to Tanglewood
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This property is like nothing you've ever seen--a gem near the top of Mt. Lebanon with 86-acres of forest, streams, wate ...
From $350 per night (USD)Expedia
From $234 per night (USD)VRBO
Shaker mid century
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
A spacious house on over 2 acres private lot - just for your enjoyment! This is our private vacation house, and we love ...
From $234 per night (USD)VRBO
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Round House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Perched on a hilltop in a Berkshire forest, this bohemian guesthouse is a unique hideaway in a silent, idyllic setting d ...
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From $145 per night (USD)VRBO
Experience the Beauty of the Berkshires and Hudson Valley in Our Historic Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to the Berkshires and step back in time with a stay in our charming historic home, conveniently located near the ...
From $145 per night (USD)VRBO
From $106 per night (USD)Expedia
Loft near Hancock Shaker Village, Birch
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Shaker Meadows, a historic 18th century Berkshires farm. This chalet-style suite in the farm’s charming 1940s ...
From $106 per night (USD)Expedia
From $400 per night (USD)VRBO
Historic New Lebanon Hideaway on 33 Private Acres!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 11
Get the cozy bed and breakfast feel all to yourself at this New Lebanon vacation rental. This sprawling home with 5 beds ...
From $400 per night (USD)VRBO
From $151 per night (USD)VRBO
Hand Hollow Haven - A Home Away From Home
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Make this 3 bedroom Berkshire cottage, with Kitchen, Dining Room, Front Room, Bathroom, and a Deck, your year-round esca ...
From $151 per night (USD)VRBO
From $350 per night (USD)VRBO
Your Dream House: Log Chalet, Sauna, Close To Skiing
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This magical very private property, built in 2011 has comfortable sleeping accommodations. The cedar wood sauna and the ...
From $350 per night (USD)VRBO
From $695 per night (USD)VRBO
A Guest House & Permaculture Sanctuary in the Berkshires
- Bedrooms:
- 9
- Bathrooms:
- 7
- Sleeps:
- 14
We are nestled in a picturesque valley between the Berkshires and the Hudson River Valley, providing a serene backdrop f ...
From $695 per night (USD)VRBO
From $400 per night (USD)VRBO
Froggy Pond - Family-Friendly Home With Incredible Views And A Private Swim Pond
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This is an adorable 3 bedroom house on 38 secluded acres. It is located ten minutes from all the amenities of Jiminy Pea ...
From $400 per night (USD)VRBO
From $410 per night (USD)Expedia
Berkshire Rural Retreat
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Our Berkshire rural retreat has been in our family for three generations where we’ve regularly rejuvenated with hiking, ...
From $410 per night (USD)Expedia
From $125 per night (USD)VRBO
Get away and get back to nature!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Connecting with nature doesn't mean you have to rough it. The Owl's Nest is a cozy campsite located in the heart of the ...
From $125 per night (USD)VRBO
From $125 per night (USD)Expedia
Escape for the weekend!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Connecting with nature doesn't mean you have to rough it. The Owl's Nest is a cozy campsite located in the heart of the ...
From $125 per night (USD)Expedia
From $125 per night (USD)VRBO
Escape from it all. Woods, birds, campfire and fresh air.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Connecting with nature doesn't mean you have to rough it. The Owl's Nest is a cozy campsite located in the heart of the ...
From $125 per night (USD)VRBO
From $240 per night (USD)Expedia
Hilltop House
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 9
About this space Hilltop House is the perfect get away for your family! Located on 15 acres, it is the best place to enj ...
From $240 per night (USD)Expedia
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Haddock + Cotter - Chic Farmhouse and Barn w\/ Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Haddock + Cotter is a beautifully restored chic + charming country home located in Old Chatham, NY. Built in 1834, the h ...
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