Lanesborough Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Nov 21 - Nov 22
Tomorrow
Nov 22 - Nov 23
This weekend
Nov 21 - Nov 23
Next weekend
Nov 28 - Nov 30

Vacation Rentals in Lanesborough

Interior
Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location

Vacation Home in Lanesborough

9.6 out of 10, Exceptional, (74)
"Beautiful house and location that was perfect for a family weekend. Would 100% recommend!"
United States
Shaun L.
Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location
Terrace/patio
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!

Vacation Home in Lanesborough

10.0 out of 10, Exceptional, (6)
"Everything was just as advertised and we really enjoyed the view and the hot tub. Perfect spot for a quick getaway! "
United States
Cindy B.
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
1 bedroom, WiFi, bed sheets
Charming Apt in 18th c Berkshire Farmhouse

Apartment in Lanesborough

9.4 out of 10, Exceptional, (39)
"It’s a nice comfortable apartment with a good kitchen. We were traveling to see a concert and some art at Mass MOCA. Patrick is a friendly and welcoming host."
United States
Roy
The price is ￥21,250
￥31,976 total
includes taxes & fees
Nov 22 - Nov 23
Charming Apt in 18th c Berkshire Farmhouse
Lobby
Vacation Village in the Berkshires

Condo in Williamstown

3.0 star property
8.8 out of 10, Excellent, (2138)
"We came here because it was off season, great price, and it had an indoor pool. "
United States
Monica
The price is ￥11,629
￥14,713 total
includes taxes & fees
Nov 23 - Nov 24
Vacation Village in the Berkshires
Exterior
Jiminy Peak Mountain Resort

Condo resort in Hancock

3.0 star property
8.2 out of 10, Very Good, (986)
"This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay."
United States
Amy
The price is ￥23,399
￥26,137 total
includes taxes & fees
Nov 22 - Nov 23
Jiminy Peak Mountain Resort
Exterior
Huttopia Berkshires

Camping in Williamstown

1.0 star property
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
The price is ￥28,805
￥32,174 total
includes taxes & fees
Dec 13 - Dec 14
Huttopia Berkshires
Indoor pool, outdoor pool, pool umbrellas, sun loungers
The Ponds at Foxhollow

Condo resort in Lenox

3.0 star property
8.6 out of 10, Excellent, (134)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
United States
Cyril
The price is ￥18,953
￥21,171 total
includes taxes & fees
Dec 5 - Dec 6
The Ponds at Foxhollow
Exterior detail
Taborton Harvest Boulder Pines Cabin in the woods

Cabin in Sand Lake

10.0 out of 10, Exceptional, (13)
"Loved the earthiness and serenity of the cabin and great room. Everything built and made and maintained by the Adamos- truly a haven "
United States
Joanna R.
The price is ￥19,676
￥29,004 total
includes taxes & fees
Nov 22 - Nov 23
Taborton Harvest Boulder Pines Cabin in the woods
Game room
Pet Friendly Riverfront Home in Great Barrington

Vacation Home in Great Barrington

9.2 out of 10, Wonderful, (5)
The price is ￥30,105
￥44,354 total
includes taxes & fees
Nov 23 - Nov 24
Pet Friendly Riverfront Home in Great Barrington
Exterior detail
The Kemble- Built by a US Secretary of State in Lenox

Villa in Lenox

10.0 out of 10, Exceptional, (17)
"Perfect house for our family reunion. Everything was perfect."
United States
Michael C.
The Kemble- Built by a US Secretary of State in Lenox
Interior
Peace and quiet on the lake

Vacation Home in Sherwood Forest

9.6 out of 10, Exceptional, (228)
"This property provides direct access to a lovely lake for kayaking and swimming. It is also a terrific location for Berkshire musts such as Jacob's Pillow and Tanglewood. The owner is quickly responsive to questions and directions for check in were easy to follow. The house has strong WiFi for any work days you have while traveling. Highly recommend and look forward to staying there again in the future! "
United States
Leslie K.
Peace and quiet on the lake
Exterior
Bear Creek Cabin

Cabin in Charlemont

10.0 out of 10, Exceptional, (42)
"We enjoyed our stay!!"
United States
Hillary S.
The price is ￥62,964
￥94,245 total
includes taxes & fees
Nov 22 - Nov 23
Bear Creek Cabin
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi

Vacation Home in Lee

8.0 out of 10, Very Good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is ￥66,899
￥124,486 total
includes taxes & fees
Dec 1 - Dec 2
Spacious 5-bedroom house in charming Lee with WiFi
Interior
Charming 3-bedroom Cabin for nature lovers

Cabin in Stephentown

7.0 out of 10, Good, (2)
"It’s a duplex, half of an old farm house. The bedrooms are all up a steep staircase to the second floor. The only bathroom is on the main floor with the kitchen and LR. It was clean but had a mild old house smell. It’s out in the country with a great view from the enclosed porch and the open deck. The kitchen was well stocked with appliances and everything worked. It needs more seating and lights in the LR. "
United States
Bill B.
The price is ￥24,399
￥50,321 total
includes taxes & fees
Nov 23 - Nov 24
Charming 3-bedroom Cabin for nature lovers
Exterior
Hancock Village Inn Near Jiminy Peak

Vacation Home in Hancock

10.0 out of 10, Exceptional, (15)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is ￥94,289
￥174,892 total
includes taxes & fees
Dec 2 - Dec 3
Hancock Village Inn Near Jiminy Peak
Exterior
Amazing Estate! 1,500-2,500 OFF NOW w/ Early Booking on 2026 week-long vacation!

Vacation Home in Old Chatham

9.6 out of 10, Exceptional, (93)
"What a lovely property. Laurie was so kind and helpful checking us in, and the house was so fun. Would absolutely stay here again. "
United States
Daniel R.
Amazing Estate! 1,500-2,500 OFF NOW w/ Early Booking on 2026 week-long vacation!
Outdoor dining
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Vacation Home in Pittsfield

9.8 out of 10, Exceptional, (149)
"We had a fabulous stay at this lovely home in the Berkshires! The house was well equipped with everything needed to make our stay with our family so enjoyable. Great communication with the host in helping to resolve a small issue with loss of power on 2nd floor but was easily resolved."
United States
Sarah A.
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Dining
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Vacation Home in Stockbridge

10.0 out of 10, Exceptional, (133)
"Clean house, well appointed, great location, responsive owner"
United States
sara m.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Property grounds
Experience Three Sisters Sanctuary in Goshen, MA

Vacation Home in Goshen

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had such a great time staying here as always. "
United States
David F.
Experience Three Sisters Sanctuary in Goshen, MA
Property grounds
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Vacation Home in Hinsdale

9.8 out of 10, Exceptional, (19)
"Rich was an amazing host. Beautiful lake and sunsets. I would love to stay there again"
United States
maria f.
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Lanesborough Hotel Reviews

The Williams Inn

The Williams Inn

10/10 Excellent
"Bb"
Stephen 2-night trip
Posted 4 days ago
The Williams Inn

Find out more about Lanesborough

Search for holiday rentals in Lanesborough on Expedia! You can easily find your home rentals, villas, holiday apartments in Lanesborough using one of the methods below:

  • View our selection of featured holiday rentals in Lanesborough
  • Use the map to find apartments and other holiday homes in the Lanesborough neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Lanesborough while they last

Look no further and take a look at our great range of rental properties in Lanesborough!

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?

Pet Friendly Riverfront Home in Great Barrington: This vacation home rental outside of Lanesborough is located on a river and has a fireplace, a garden, and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms in addition to a kitchen with a stovetop and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Lanesborough?

Choose from 11 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 Crane Museum of Papermaking and Jiminy Peak Mountain Resort.

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.