Town of New Lebanon Rentals
From $184 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 $184 per night (USD)VRBO
From $311 per night (USD)Expedia
Historic Berkshires Home Near Tanglewood, Trails & Wineries
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to the Hudson Valley and Berkshires this summer with a stay in our beautifully restored 1800s home, ideally locat ...
From $311 per night (USD)Expedia
From $379 per night (USD)VRBO
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond
- Bedrooms:
- 1
- 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 $379 per night (USD)VRBO
From $165 per night (USD)VRBO
Berkshires Charming 4br/2ba, Fireplaces, scr porch Now-9/7/25, OR 9/7/25-5/15/26
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
BERKSHIRES - 4 BR/2BA, Avail Now-9/7/25, OR 9/7/25-5/15/26- CHARMING, BEAUTIFULLY DECORATED (CHECK PHOTOS PLEASE) 1,800 ...
From $165 per night (USD)VRBO
From $383 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 $383 per night (USD)VRBO
From $922 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 $922 per night (USD)VRBO
From $464 per night (USD)VRBO
Restored historic farmhouse on 25 private acres
- Bedrooms:
- 2
- 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 $464 per night (USD)VRBO
From $1521 per night (USD)VRBO
20 minutes to Jiminy Peak and Bousquet Mountain
- Bedrooms:
- 5
- 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 $1521 per night (USD)VRBO
From $314 per night (USD)VRBO
20 minutes to Jiminy Peak and Bousquet Mountain
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This property is like nothing you've ever seen--a gem near the top of Mt. Lebanon with 75-acres of forest, streams, wate ...
From $314 per night (USD)VRBO
From $686 per night (USD)VRBO
Haddock and Cotter a Charming Countryside Stay with Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This beautifully restored 1834 farmhouse blends historic charm with chic, modern comfort. Perfect for hosting family and ...
From $686 per night (USD)VRBO
From $157 per night (USD)VRBO
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 $157 per night (USD)VRBO
From $295 per night (USD)Expedia
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 $295 per night (USD)Expedia
From $1637 per night (USD)VRBO
Guesthouse & Permaculture Sanctuary in the Berkshires
- Bedrooms:
- 8
- 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 $1637 per night (USD)VRBO
From $494 per night (USD)VRBO
Historic New Lebanon Hideaway on 33 Private Acres!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Get the cozy bed and breakfast feel all to yourself at this New Lebanon vacation rental. This sprawling home with 5 beds ...
From $494 per night (USD)VRBO
From $778 per night (USD)VRBO
Den Outdoors Cabin With STUNNING Adirondack Views - EV charging available
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Set on a sprawling 7-acre property, this tranquil retreat offers the perfect blend of rustic charm and modern comfort. ...
From $778 per night (USD)VRBO
From $278 per night (USD)VRBO
Berkshire Hideaway w/ Fire Pit & Playground!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Near Wineries & Historical Sites | Screened Porch | Peaceful Location Fine wines, scenic landscapes, and quality family ...
From $278 per night (USD)VRBO
From $874 per night (USD)VRBO
Spacious 7 bedroom house, Near jiminy Peak in Hancock ma , In the Berkshires
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 15
Discover this delightful 7-bedroom gem in New Lebanon. This fabulous house boasts 1 king bed, 3 queen beds, 2 twin beds, ...
From $874 per night (USD)VRBO
From $172 per night (USD)Expedia
NEW RENO - Historic Loft w/views of the Berkshires
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Shaker Meadows, a historic 18th century Berkshires farm. This newly renovated chalet-style suite in the farm’ ...
From $172 per night (USD)Expedia
From $167 per night (USD)VRBO
NEW RENO - Chalet-style farm loft near Tanglewood
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Welcome to Shaker Meadows, a historic 18th century Berkshires farm. This newly renovated chalet-style loft in the farm’s ...
From $167 per night (USD)VRBO
From $239 per night (USD)Expedia
Airy Upstate Getaway with a View
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your perfect getaway in New Lebanon! This open and spacious home offers stunning views of the New Lebanon Val ...
From $239 per night (USD)Expedia
From $157 per night (USD)VRBO
Beautiful 2-bedroom apartment in New Lebanon
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to this apartment in picturesque New Lebanon. This cozy retreat features 2 bedrooms with a queen and full bed, a ...
From $157 per night (USD)VRBO
From $99 per night (USD)VRBO
Spacious 1-bedroom apartment in peaceful East Chatham with WiFi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Your peaceful apartment in East Chatham with one comfortable bedroom featuring a queen bed. Enjoy the convenience of 1 1 ...
From $99 per night (USD)VRBO
From $345 per night (USD)VRBO
Artists’ Hideaway in Old Chatham
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Hilltop Oasis, a one-of-a-kind retreat where rustic textures meet modern comfort in the heart of Old Chatham. ...
From $345 per night (USD)VRBO
From $345 per night (USD)Expedia
Artists’ Hideaway in Old Chatham
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Hilltop Oasis, a one-of-a-kind retreat where rustic textures meet modern comfort in the heart of Old Chatham. ...
From $345 per night (USD)Expedia