Lanesborough, MA Vacation Homes from ￥32,405

A tower with a green glass dome and intricate carvings.

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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 Lebanon

Joanna P.

￥32,868 total

includes taxes & fees

Oct 19 - Oct 20

2. Comfortable Berkshires retreat on mtn resort, SISO

Hancock

Amit

￥85,590 total

includes taxes & fees

Oct 18 - Oct 19

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!

Pittsfield

Stephen L.

￥77,858 total

includes taxes & fees

Oct 25 - Oct 26

A spacious living room with a dining area, a kitchen, and a large window.

4. 1800s Carriage house in Berkshires / Hudson Valley

New Lebanon

Leslie H.

￥35,593 total

includes taxes & fees

Nov 15 - Nov 16

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

Stephentown

Robert B.

￥89,280 total

includes taxes & fees

Oct 28 - Oct 29

A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

6. Hancock Village Inn Near Jiminy Peak

Hancock

Price F.

￥171,062 total

includes taxes & fees

Oct 20 - Oct 21

A white two-story house with a porch, surrounded by trees and a hill.

7. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

Canaan

Christine C.

￥74,997 total

includes taxes & fees

Oct 18 - Oct 19

A wooden kitchen with a central island, bar stools, and a dining table with chairs.

8. Cozy Home in Pownal VT

Pownal

Jess M.

￥32,405 total

includes taxes & fees

Oct 20 - Oct 21

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.

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

Richmond

￥109,210 total

includes taxes & fees

Nov 15 - Nov 16

A patio with a wooden table and benches, a grill, and a garden with trees and flowers.

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

New Lebanon

Anonymous traveler

￥90,775 total

includes taxes & fees

Oct 27 - Oct 28

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

Sherwood Forest

William C B.

￥50,329 total

includes taxes & fees

Nov 3 - Nov 4

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

Williamstown

Michelle B.

￥97,782 total

includes taxes & fees

Oct 26 - Oct 27

A living room with a sofa, armchairs, a coffee table, and a television.

13. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

Patricia O.

￥100,381 total

includes taxes & fees

Oct 30 - Oct 31

A kitchen with white cabinets, a wooden dining table, and pendant lights.

14. A roomy remodeled retreat close to MassMoCA

North Adams

Diane

￥76,605 total

includes taxes & fees

Oct 20 - Oct 21

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.

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

Sherwood Forest

Sharon K.

￥59,302 total

includes taxes & fees

Oct 27 - Oct 28

A modern living room with a sofa, armchair, coffee table, and TV.

16. Spacious Central Berkshires Home for Groups

Lee

neil s.

￥94,921 total

includes taxes & fees

Oct 19 - Oct 20

A two-story house with a porch, surrounded by trees and snow.

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

Bennington

Malika R.

￥55,136 total

includes taxes & fees

Oct 20 - Oct 21

A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

18. Greylock Cabin

Florida

Margaret M.

￥68,687 total

includes taxes & fees

Nov 12 - Nov 13

A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

19. Secluded Family Home in Serene Stockbridge Woods

Stockbridge

Ofer C.

￥102,040 total

includes taxes & fees

Oct 20 - Oct 21

A hallway with a wooden floor, a white wall with framed pictures, a staircase, and a door with a window.

20. Stylish Mid-century Modern Berkshires Cape

Lee

H B.

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Top Lanesborough Hotel Reviews

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"We were able to get rental as a last minute deal for a villa here and we're very pleased with the property. The two rooms were very spacious each with its own bathroom, one with jacuuzi. Was quiet and you don't see or hear neighbor next to you. The rooms were quite roomy. All amenities in kitchen and nice livingroom/dining area. Nice outdoor seating with table and nice view of mountains. Only issue encountered was figuring out how the showers worked, figured it out by pulling down a round lever on bottom of faucet. Very clean and spacious, nice experience."

Courtyard by Marriott Lenox Berkshires

8/10 Good

"Property was clean and in excellent shape overall. Pros: Food at the Bistro was excellent quality, and large portions. Room was clean and comfortable, slept well while staying there. Onsite laundry was a very helpful option and the washer and dryer, while expensive at $4.00 a load, were in excellent condition and did the job very well. Pool and hot tub were excellent. Cons: The light switches governing the various lights in the room were a little confusing at first. The free HBO had severe buffering issues, making watching anything on it tough. The controls for the automatic curtain open/shut were broken, making one start the open and shut manually. Overall, the Pros well outweighed the Cons."

Vacation Village in the Berkshires

10/10 Excellent

"The staff was very helpful. The were lots of activities offered including the pool, hot tub, movie theater , and renting movies for free. The unit was very spacious and comfortable. We could hear the people above us stomping around a bit but that’s to be expected."

Jiminy Peak Mountain Resort

8/10 Good

"Everything was great here except our keys did not work so I had to go back to front desk for new keys on check in. Then on our 2nd morning we went to breakfast and came back to keys not working again. Front desk was helpful and reprogrammed them right away so not a huge deal. The hotel also has pretty thin walls so noise travels. Luckily our neighbors for the weekend were mostly quiet. I wish we knew John Harvards was closed till Thanksgiving but the other pub was great with an excellent beer selection on tap, great service & live entertainment every night. I wish there was free breakfast but thats not a big deal. I would recommend this place especially if you like to ski. We will consider this location for future Berkshire trips as its a fairly good central county location. Just keep in mind most shopping and restaurants are about 15-20+ minutes away."

Find out more about Lanesborough

Lanesborough Vacation Homes information

Number of reviews	240
Accommodation	303 Vacation Homes
Lowest Price	￥32,405
Highest Price	￥171,062

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Lanesborough vacation homes

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

2. Comfortable Berkshires retreat on mtn resort, SISO

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

4. 1800s Carriage house in Berkshires / Hudson Valley