Photo by Caitlin Reese

Search Vacation Homes in Lanesborough

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Compare 228 Vacation Homes in Lanesborough with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (239)
"Property was very nice Kirchen could use some additons -starting with a ladle "
The price is SAR 563
SAR 855 total
includes taxes & fees
17 Feb - 18 Feb
Berkshire Village Carriage House - Super Private!!

Peace and quiet on the lake

9.6 out of 10, Exceptional, (208)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
Peace and quiet on the lake

Charlemont Retreat on Chickley River w/ EV Charger

9.6 out of 10, Exceptional, (25)
"Our group was 7 adults and 1 dog for a ski weekend and we were very pleased with our stay. The house was clean, cozy, well-stocked, and comfortable for all of us to cook, eat and socialize together. We loved the ample supply of board games, clean and modern bathrooms, the wood burning stove, and historic charm of the house. The host was very responsive and made it easy to contact him if we needed anything. We would absolutely consider this property again when visiting in the future. "
Charlemont Retreat on Chickley River w/ EV Charger

Berkshires Lakefront Retreat

10.0 out of 10, Exceptional, (5)
"I booked the weekend for my girlfriends birthday with a couple of her friends. The game room was a massive hit as was the propane fireplace outside. We also enjoyed watching the snow fall on the frozen lake. William was very responsive to messages and calls. We enjoyed our stay immensely and are hoping to come back in the summer"
Berkshires Lakefront Retreat

Amore Estate - beautiful room with many places to explore and relax in.

9.4 out of 10, Exceptional, (21)
"Fantastic, large house with tons of places to explore in the house and on the property. We came for a long weekend with 3 families and both the adults and kids felt quickly at home and really enjoyed our stay. We cannot wait to some back!"
Amore Estate - beautiful room with many places to explore and relax in.

Comfortable Berkshires retreat on mtn resort, SISO

The price is SAR 1,208
SAR 2,524 total
includes taxes & fees
23 Feb - 24 Feb
Comfortable Berkshires retreat on mtn resort, SISO

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

10.0 out of 10, Exceptional, (65)
"Great stay! Kids and adults both loved it and very easy to access the slopes. "
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Country Living just minutes from Everything!

10.0 out of 10, Exceptional, (27)
"Very nice, very clean property. Everything you need. Communication with owner is excellent. My family and I were extremely comfortable here!"
Country Living just minutes from Everything!

Hearts Desire is a furnished whole house in a small, colorful garden center.

10.0 out of 10, Exceptional, (88)
"We have been staying here at least once a year to ski at the nearby mountains for the past several years. The home is spotless and the amenities are top notch. The house has everything you need to cook a great meal, a huge TV for a cozy movie night, comfortable king beds and the awesome, squeaky clean hot tub. The home is far enough out of town so you feel like you're getting away, while being minutes away from attractions, restaurants and stores. Thank you for sharing your home! We're already...
Hearts Desire is a furnished whole house in a small, colorful garden center.

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.6 out of 10, Exceptional, (10)
"As advertised "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (13)
"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...
Pristine Home In Becket Woods

Two Brooks Lodge | Hot Tub | Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

8.8 out of 10, Excellent, (28)
"Rustic but not too rustic, great location, excellent hot tub, plenty of blankets, well-appointed kitchen. Would definitely stay again. "
The price is SAR 525
SAR 1,183 total
includes taxes & fees
18 Feb - 19 Feb
Two Brooks Lodge | Hot Tub | Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (9)
"Annual mother/son ski and food fest!Lots of fun with family and friends. Plenty of space for everyone.. Kitchen wascwell"
The price is SAR 2,430
SAR 4,113 total
includes taxes & fees
25 Feb - 26 Feb
Hancock Village Inn at Jiminy Peak

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (11)
"The house was perfect for us. Spacious, clean, comfortable. Beds comfortable. Bathrooms really nice. The road in the development is dirt, a 4wd is needed as stated. It was muddy and rutty on arrival, then snow and ice , but do-able. Great house. Would recommend "
Quintessential 6-BR Berkshires Lodge

Chic Pittsfield Home With A View!

8.6 out of 10, Excellent, (10)
"This property was just as shown in the listing and met our needs very well. It was well appointed and had many inviting areas to gather and relax in. The kitchen was well equipped and easy to use. Some very nice touches with closets and bathroom storage areas that made staying there user friendly. "
Chic Pittsfield Home With A View!

Wellspring by AvantStay | Indoor Pool + Views

10.0 out of 10, Exceptional, (10)
"We all enjoyed our stay. The house and indoor pool were wonderful. There are plenty of comfortable places to sit and enjoy the gorgeous views. We loved the location which is both close to Lenox restaurants, as well as, the southern Berkshires for food markets and activities for kids. The property manager was attentive, and the owner was very responsive. We loved our week at this family friendly property and highly recommend it. "
Wellspring by AvantStay | Indoor Pool + Views

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

10.0 out of 10, Exceptional, (118)
"Property as described. Great location to towns. Larger interior space than anticipated. Great Kitchen for a group of 5 to cook, chat and enjoy! Overall a warm and spacious home for old college friends to reunite. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (19)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
The price is SAR 533
SAR 1,318 total
includes taxes & fees
24 Feb - 25 Feb
Near Tanglewood: Historic Summer Retreat

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.4 out of 10, Exceptional, (40)
"We have stayed here twice and it is a great spot, located a few minute drive north of downtown Lenox. The house is cozy yet spacious and is great for our family to stay in while visiting family in the area. We used the kitchen to cook a meal during one of the stays and we had everything we needed. There is an air hockey table in the basement which the kids enjoyed. The house is on a main road, but it was still easy enough to pull in and out of and the noise of the road did not bother us at all....
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Stunning lake views and privacy only mins. to downtown Lenox, Stockbridge, Lee.

10.0 out of 10, Exceptional, (22)
"This was our third year in a row staying at this house for our annual ski trip with 4 adults and 6 kids. It is always immaculate and has great common rooms for all of us. Kari and Glenn think of everything and Glenn even came to shovel the walkway and driveway for us during a snow storm (without even having to enter the house). We look forward to our time at this beautiful property every year! "
Stunning lake views and privacy only mins. to downtown Lenox, Stockbridge, Lee.
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.
Don't see what you're looking for?
See all available properties in Lanesborough
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Lanesborough

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (239)
"Property was very nice Kirchen could use some additons -starting with a ladle "
The price is SAR 563
SAR 855 total
includes taxes & fees
17 Feb - 18 Feb
Berkshire Village Carriage House - Super Private!!

Charming historic cottage on scenic road to Mt. Greylock

10.0 out of 10, Exceptional, (107)
"We had a great stay- no complaints! Very close to Jiminy Peak, where we were skiing, and the house was very comfortable. Thank you!"
Charming historic cottage on scenic road to Mt. Greylock

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1760)
"Great place "
The price is SAR 431
SAR 511 total
includes taxes & fees
23 Feb - 24 Feb
Vacation Village in the Berkshires
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.