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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Lanesborough vacation homes

A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

1. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is AED 257
AED 764 total
includes taxes & fees
20 Oct - 21 Oct
NEW RENO - Chalet-style farm loft near Tanglewood
Pool

2. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.8 out of 10, Excellent, (12 reviews)
"Host was proactive in communication and answer each and every question."
United States
Amit
The price is AED 657
AED 2,067 total
includes taxes & fees
14 Nov - 15 Nov
Comfortable Berkshires retreat on mtn resort, SISO
A wooden deck with a table and chairs, surrounded by a white railing.

3. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
8.4 out of 10, Very good, (10 reviews)
"Very comfortable and clean accommodations in a nice neighborhood, and a great deck to appreciate the view."
United States
Stephen L.
The price is AED 988
AED 1,810 total
includes taxes & fees
25 Oct - 26 Oct
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
A spacious living room with a dining area, a kitchen, and a large window.

4. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
The price is AED 312
AED 827 total
includes taxes & fees
9 Nov - 10 Nov
1800s Carriage house in Berkshires / Hudson Valley
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

5. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.8 out of 10, Exceptional, (8 reviews)
"A lovely house! Very convenient for a Tanglewood weekend."
United States
Robert B.
The price is AED 646
AED 2,075 total
includes taxes & fees
20 Oct - 21 Oct
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A white two-story house with a porch, surrounded by trees and a hill.

6. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "
United States
Christine C.
The price is AED 727
AED 1,729 total
includes taxes & fees
20 Oct - 21 Oct
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

7. Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (22 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is AED 2,117
AED 3,976 total
includes taxes & fees
20 Oct - 21 Oct
Hancock Village Inn Near Jiminy Peak
A wooden kitchen with a central island, bar stools, and a dining table with chairs.

8. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (11 reviews)
"Absolutely wonderful place to stay. Quiet, clean, comfortable and close to a lot of things while feeling secluded. Owner communicated quickly and entry was easy. Loved every minute of our stay."
United States
Jeri R.
The price is AED 426
AED 753 total
includes taxes & fees
20 Oct - 21 Oct
Cozy Home in Pownal VT
A bedroom with a bed, a nightstand, a lamp, a chair, and a dresser.

9. Mayas Shangrila

Mayas Shangrila
2.0 star property
Richmond
The price is AED 2,983
AED 4,260 total
includes taxes & fees
31 Oct - 1 Nov
Mayas Shangrila
A modern living room with a grey sectional sofa, a brown leather ottoman, a woven rug, a dining table with chairs, and a view through large windows.

10. Ellie’s Overlook, best view in the Berkshires!

Ellie’s Overlook, best view in the Berkshires!
Richmond
The price is AED 1,157
AED 2,538 total
includes taxes & fees
25 Oct - 26 Oct
Ellie’s Overlook, best view in the Berkshires!
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

11. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.4 out of 10, Exceptional, (3 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is AED 242
AED 1,132 total
includes taxes & fees
3 Nov - 4 Nov
Real Estate: Therapy - Lake, Laundry, Love it
A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

12. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Williamstown
10.0 out of 10, Exceptional, (2 reviews)
"Easy breezy, short walk to walk into town/Williams Campus. Down to Earth, yet sophisticated vibe, great art scene. "
United States
Michelle B.
The price is AED 1,116
AED 2,273 total
includes taxes & fees
20 Oct - 21 Oct
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
A kitchen with white cabinets, a wooden dining table, and pendant lights.

13. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (61 reviews)
"Cute and comfy home. We enjoyed the unique decor and lack of TVs everywhere. It was a great break from all the crazy. Lots of conversation and togetherness."
United States
Diane
The price is AED 841
AED 1,768 total
includes taxes & fees
28 Oct - 29 Oct
A roomy remodeled retreat close to MassMoCA
A patio with a wooden table and benches, a grill, and a garden with trees and flowers.

14. NEW RENO Historic Creamery in Berkshires w/hot tub

NEW RENO Historic Creamery in Berkshires w/hot tub
New Lebanon
10.0 out of 10, Exceptional, (8 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveler
The price is AED 1,021
AED 2,109 total
includes taxes & fees
27 Oct - 28 Oct
NEW RENO Historic Creamery in Berkshires w/hot tub
A living room with a sofa, armchairs, a coffee table, and a television.

15. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
10.0 out of 10, Exceptional, (11 reviews)
"We had a lovely stay! The home was so well equipped and comfortable. Beautiful area, great restaurant choices and staying here made our Miraval experience perfect."
United States
Patricia O.
The price is AED 1,167
AED 2,329 total
includes taxes & fees
20 Oct - 21 Oct
Sun Filled Lenox Retreat - Minutes to Tanglewood!
A cozy living room with a wooden bookshelf, a sofa set, a dining table with chairs, and a patterned rug.

16. Mayas Shangrila - Historic 200-Year-Old Farmhouse on 4 Secluded Acres in the Berkshires

Mayas Shangrila - Historic 200-Year-Old Farmhouse on 4 Secluded Acres in the Berkshires
Richmond
The price is AED 3,309
AED 4,619 total
includes taxes & fees
21 Oct - 22 Oct
Mayas Shangrila - Historic 200-Year-Old Farmhouse on 4 Secluded Acres in the Berkshires
A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

17. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (10 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AED 536
AED 1,382 total
includes taxes & fees
26 Oct - 27 Oct
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A modern living room with a sofa, armchair, coffee table, and TV.

18. Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
9.6 out of 10, Exceptional, (4 reviews)
"house was very clean, spacious and well equipped with everything we needed. Great communication with the host. Perfect location for our trip to Tanglewood."
United States
neil s.
The price is AED 1,074
AED 2,201 total
includes taxes & fees
20 Oct - 21 Oct
Spacious Central Berkshires Home for Groups
A two-story house with a porch, surrounded by trees and snow.

19. Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
Bennington
8.6 out of 10, Excellent, (36 reviews)
"The location was quite and peaceful. We enjoyed our stay and were suprised how great the wifi was for the location."
United States
Malika R.
The price is AED 676
AED 1,421 total
includes taxes & fees
23 Oct - 24 Oct
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

20. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
10.0 out of 10, Exceptional, (30 reviews)
"We had a wonderful time, we’d be happy to come back again "
United States
Ofer C.
The price is AED 1,253
AED 2,372 total
includes taxes & fees
20 Oct - 21 Oct
Secluded Family Home in Serene Stockbridge Woods
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Lanesborough Hotel Reviews

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

8/10 Good
"Cuisine bien équipée beau site. Un peu vieillot. La porte du lave vaisselle était brisée mais il fonctionnait tout de même bien. On avait un bac avec sel et poivre et sucre en plus que des filtres et sachets à café. Un beau gros four/air fryer dans la chambre également qui était très pratique. Des couverts pour 6 personnes.Jy retournerais sans hésitation . Le lit était confortable. Les oreillers un peu moins"
Gabriel 2-night trip
Posted 2 hours ago
Jiminy Peak Mountain Resort