Photo by Caitlin Reese

Lanesborough Holiday Rentals

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Holiday Rentals in Lanesborough

Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (220)
"A quick weekend! Repeat guests! Place is always immaculate- and easy check in/check out. "
The price is HK$1,111
HK$1,710 total
includes taxes & fees
11 Nov - 12 Nov
Berkshire Village Carriage House - Super Private!!
Charming historic cottage on scenic road to Mt. Greylock
Outdoor dining
Charming historic cottage on scenic road to Mt. Greylock
10.0 out of 10, Exceptional, (103)
"Great cottage, pretty much at the foot of Mount Greylock - very spacious and comfortable - in the country but close to many of the towns of the Berkshires - the hosts Cheryl and Rich were very kind and informative about the area -thank you Cheryl and Rich - I hope to return sometime -"
Charming historic cottage on scenic road to Mt. Greylock
Hearts Desire is a furnished whole house in a small, colorful garden center.
Exterior detail
Hearts Desire is a furnished whole house in a small, colorful garden center.
10.0 out of 10, Exceptional, (81)
"Hearts Desire has become my home away from home when visiting my daughter at Williams. Further, she and her friends can come visit for a home cooked meal. Great location and the hot tub with coffee in the AM or with an old fashion in the evening became a ritual. Also great viewing of the fall colors. Will continue to make this my home when I visit New England. "
Hearts Desire is a furnished whole house in a small, colorful garden center.
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Miscellaneous
Cozy Rustic Apt in 18th c Berkshire Farmhouse
9.6 out of 10, Exceptional, (60)
"Beautiful property with flower farm, pick your own berries and vegetable farm stand. Rustic log cabin feel with all amenities needed with kitchen."
The price is HK$1,127
HK$1,679 total
includes taxes & fees
11 Nov - 12 Nov
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1743)
"The suite was clean, comfortable, and ready when I arrived."
The price is HK$1,312
HK$1,517 total
includes taxes & fees
8 Nov - 9 Nov
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (914)
"Nice fall view"
The price is HK$1,158
HK$1,270 total
includes taxes & fees
8 Nov - 9 Nov
Jiminy Peak Mountain Resort
Pristine Home In Becket Woods
Fridge, microwave, oven, stovetop
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
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Exterior
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (208)
"The Cabin Had All The Amenities You Would Need and With A Quiet and Serene Area. For Me It Was Relaxing Stay!"
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Peace and quiet on the lake
Interior
Peace and quiet on the lake
9.6 out of 10, Exceptional, (195)
"My husband and I loved our stay there.. The house was very clean with a beautiful scenic back yard. Enjoyed the porch and the view of the lake. Easy check in and check out.. I would highly recommend this place."
Peace and quiet on the lake
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
TV, fireplace, DVD player, books
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
7.2 out of 10, Good, (41)
"We had expectations of a peaceful rustic cabin in the woods, and this rental checked almost all of the boxes! The quaint town of Great Barrington was just close enough for convenience, but the house was rural enough to help us all relax and enjoy the quiet. We loved the dock and the firepit, and the house was well-stocked with firewood, towels, and toiletries. "
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Berkshires Cabin 2 Mi to Appalachian Trail!
TV, fireplace, books
Berkshires Cabin 2 Mi to Appalachian Trail!
9.8 out of 10, Exceptional, (9)
"Enjoyed the foliage and some nice hikes. House was comfortable and clean. Owner was responsive and helpful. We arrived at night and had trouble locating the property when our gps failed. Owner was helpful guiding us to the house. I suggest arriving in the light of day. "
Berkshires Cabin 2 Mi to Appalachian Trail!
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Exterior
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
9.6 out of 10, Exceptional, (125)
"We stayed two days but were mostly for sleep and sightseeing/visits. Certainly fit the bill for our needs. Would recommend to friends "
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Berkshire Lake access
Lake
Berkshire Lake access
10.0 out of 10, Exceptional, (47)
"The house was very clean and the yard is large. It's a great place for family vacations."
Berkshire Lake access
Bear Creek Cabin
Exterior
Bear Creek Cabin
9.8 out of 10, Exceptional, (20)
"Nestled on the woods Perfect for our family wedding 15 min away"
The price is HK$3,109
HK$4,680 total
includes taxes & fees
10 Nov - 11 Nov
Bear Creek Cabin
Beautiful One-of-a Kind Estate! Pool, Gym, Trails & More! 1,000 off 2025 stays!
Fridge, microwave, oven, stovetop
Beautiful One-of-a Kind Estate! Pool, Gym, Trails & More! 1,000 off 2025 stays!
9.6 out of 10, Exceptional, (84)
"This large home has many comfortable bedrooms, some very large suites. The kitchen is very well stocked. Our family had a wonderful stay. The pool was great, and a center of our enjoyment. Kids also enjoyed the game room."
Beautiful One-of-a Kind Estate! Pool, Gym, Trails & More! 1,000 off 2025 stays!
Quintessential 6-BR Berkshires Lodge
Exterior
Quintessential 6-BR Berkshires Lodge
9.8 out of 10, Exceptional, (8)
"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "
Quintessential 6-BR Berkshires Lodge
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Dining
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
10.0 out of 10, Exceptional, (116)
"As with our previous several stays, we thoroughly enjoyed the comfort and location of the house. We had a great time and can’t wait to do it all over again next Summer. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Amore Estate - beautiful room with many places to explore and relax in.
Fridge, microwave, oven, stovetop
Amore Estate - beautiful room with many places to explore and relax in.
9.8 out of 10, Exceptional, (16)
"Clean, house has plenty of room. Lovely property. "
Amore Estate - beautiful room with many places to explore and relax in.
The Kemble- Built by a US Secretary of State in Lenox
Exterior detail
The Kemble- Built by a US Secretary of State in Lenox
10.0 out of 10, Exceptional, (16)
"We were a big group..16 adults and 7 children. The families with children were well situated with nearby or adjacent rooms. Everyone had comfortable rooms which afforded privacy and quiet times. Each room had its own beautiful newly renovated bathrooms ( with great water pressure). The living and dining rooms were large and comfortable. The dining table was a loooong table with benches all around which easily sat our crowd. The backyard was gorgeous with beautiful views of the distant mountains....
The Kemble- Built by a US Secretary of State in Lenox
Stockbridge Home, Come Experience The Berkshires!
Fridge, microwave, oven, stovetop
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (23)
"This was the perfect spot for two California couples exploring the Berkshires. The home was warm and inviting, with enough room not to feel crowded. A welcome respite after a day of hiking, museum tours and shopping. All of which were conveniently near by... It was lovely. "
Stockbridge Home, Come Experience 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.
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Other types of properties in Lanesborough you may be interested in

Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (220)
"A quick weekend! Repeat guests! Place is always immaculate- and easy check in/check out. "
The price is HK$1,111
HK$1,710 total
includes taxes & fees
11 Nov - 12 Nov
Berkshire Village Carriage House - Super Private!!
The Red Lion Inn
Outdoor pool, pool loungers
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (1000)
"The Autumn display, the charming setting The seating arrangement in the lobby Lended itself to conversation. "
The price is HK$1,135
HK$1,616 total
includes taxes & fees
14 Nov - 15 Nov
The Red Lion Inn
Life House Berkshires
Lobby
Life House Berkshires
3.5 star property
9.0 out of 10, Wonderful, (434)
"Fun and funky spot with very friendly and helpful staff. "
The price is HK$839
HK$938 total
includes taxes & fees
11 Nov - 12 Nov
Life House 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.

Frequently asked questions

Can I find holiday rentals in Lanesborough?

Yes, there are holiday rentals close to the most popular sights in Lanesborough, or you can select a more secluded option if you're looking for a relaxing stay. Lanesborough is known for its ski areas and forests. Make sure you have time to check out the sporting events while you're in the area.

What are some of the best holiday rentals that Lanesborough has to offer?

Berkshire Village Carriage House - Super Private!!: This highly rated holiday home rental in Lanesborough is located in the mountains, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of books in this rental home to help you unwind.

How many holiday rentals are there in Lanesborough?

Choose from 12 Expedia holiday rentals in Lanesborough for a memorable holiday.

What can I see and do in Lanesborough?

Mount Greylock State Reservation Visitor Center and Mount Greylock State Reservation are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Jiminy Peak Mountain Resort and Berkshire Museum.

What are holiday rentals like in Lanesborough?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Lanesborough. Holiday rentals feature amenities like laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for family trips or small group gatherings.