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Lanesborough Vacation Rentals

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Vacation 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, (231)
"A beautiful lodge nestled in the woods surrounded by an abundance of trails to hike. "
The price is ￥22,821
￥34,919 total
includes taxes & fees
Dec 30 - Dec 31
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, (104)
"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
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 ￥22,665
￥33,915 total
includes taxes & fees
Dec 24 - Dec 25
Cozy Rustic Apt in 18th c Berkshire Farmhouse
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, (85)
"It was gorgeous, and we had a wonderful cozy time. "
Hearts Desire is a furnished whole house in a small, colorful garden center.
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, (1750)
"Nice and quiet family get a way"
The price is ￥29,308
￥33,714 total
includes taxes & fees
Jan 1 - Jan 2, 2025
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, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is ￥29,543
￥32,408 total
includes taxes & fees
Jan 5 - Jan 6, 2025
Jiminy Peak Mountain Resort
Peace and quiet on the lake
Interior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (200)
"My family and I really enjoyed our stay at the lake. My kids enjoyed playing outside in the snow. We had such a quality family time playing board games, watching movies and drinking hot cocoa. Justin was such a great host and really helpful when needed. We’re definitely coming back!"
Peace and quiet on the lake
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, (209)
"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
Berkshires Cabin 2 Mi to Appalachian Trail!
TV, fireplace, books

Berkshires Cabin 2 Mi to Appalachian Trail!

9.6 out of 10, Exceptional, (10)
"The hosts were extremely responsive and helpful, providing us with hiking ideas, questions regarding the house and suggesting best shopping spots for incidentals. The living room was cozy, seating five comfortably. The kitchen was well stocked so cooking a Thanksgiving meal was a pleasure. We thoroughly enjoyed ourselves."
Berkshires Cabin 2 Mi to Appalachian Trail!
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!
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, (127)
"A cozy spot to watch the snow come down!"
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Bear Creek Cabin
Exterior

Bear Creek Cabin

9.8 out of 10, Exceptional, (22)
"It was beautiful to wake up the first morning to see freshly fallen snow! Easy to get to, lots for the kids to do, wonderful place to share with my family for Thanksgiving! Only thing that I would change is having wood in the wood holder by the stove so that we didn’t have to carry it in. Would recommend to others. "
The price is ￥50,019
￥78,396 total
includes taxes & fees
Dec 24 - Dec 25
Bear Creek Cabin
Berkshire Lake access
Lake

Berkshire Lake access

10.0 out of 10, Exceptional, (48)
"The house worked was exceptionally clean and worked great for us. The landowner was exceptionally helpful in providing suggestions. We loved visiting the Norman Rockwell Museum and walking around Lenox. Thanks for everything!"
Berkshire Lake access
Beautiful 5-Star Private Estate! Inquire about our Early Booking Reduced Rates!
Fridge, microwave, oven, stovetop

Beautiful 5-Star Private Estate! Inquire about our Early Booking Reduced Rates!

9.6 out of 10, Exceptional, (85)
"We had fun! Game room great! Spacious and comfortable. Never got to enjoy outdoors, so maybe another trip in the future!"
Beautiful 5-Star Private Estate! Inquire about our Early Booking Reduced Rates!
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
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.

9.6 out of 10, Exceptional, (18)
"There was plenty of room for four families. Beds were comfy. If you plan on cooking you might want to bring your own knives and pans. Teflon pans were scraped . Only metal utensil available to flip pancakes. "
Amore Estate - beautiful room with many places to explore and relax in.
Chic Pittsfield Home With A View!
Property grounds

Chic Pittsfield Home With A View!

9.0 out of 10, Wonderful, (9)
"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!
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, (117)
"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
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
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, (231)
"A beautiful lodge nestled in the woods surrounded by an abundance of trails to hike. "
The price is ￥22,821
￥34,919 total
includes taxes & fees
Dec 30 - Dec 31
Berkshire Village Carriage House - Super Private!!
Hotel Downstreet
Hypo-allergenic bedding, laptop workspace, blackout drapes

Hotel Downstreet

3.0 star property
8.6 out of 10, Excellent, (1001)
"Stayed for a weekend wedding and it was a great location. Room was large "
The price is ￥18,148
￥20,271 total
includes taxes & fees
Jan 6 - Jan 7, 2025
Hotel Downstreet
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1004)
"This hotel was awesome! We enjoyed the hot tub along with the fireplace in our room! "
The price is ￥15,146
￥16,917 total
includes taxes & fees
Jan 2 - Jan 3, 2025
The Yankee, Trademark Collection by Wyndham
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 vacation rentals in Lanesborough?

Yes, we have vacation rentals close to the most popular sights in Lanesborough, or you can go with a more secluded option if you'd like a relaxing place to 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 vacation rentals in Lanesborough?

Berkshire Village Carriage House - Super Private!!: Visitors give good reviews to this Lanesborough vacation home rental, which is located in the mountains and has a garden, a barbecue grill, 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 the books in this rental home to help you unwind.

How many vacation rentals are there in Lanesborough?

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

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 larger area, you’ll find Jiminy Peak Mountain Resort and Berkshire Museum.

What are vacation rentals like in Lanesborough?

Vacation rentals are private properties you can book for a couple days or more in Lanesborough. Vacation rentals provide amenities like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a small group gathering.