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Lanesborough Vacation Rentals

Q: What are some of the best vacation rentals in Lanesborough?

Experience Three Sisters Sanctuary in Goshen, MA : This vacation home rental outside of Lanesborough is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay.

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Dates

November 2026

December 2026

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Our top choices for Lanesborough vacation rentals

1. Berkshire Mountain Lodge

Pittsfield

Susan J

AED 397 total

includes taxes & fees

6 Dec - 7 Dec

2. Vacation Village in the Berkshires

Williamstown

Carol

AED 370 total

includes taxes & fees

12 Nov - 13 Nov

A cozy living room with a large window, wooden walls, and a television.

3. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Hancock

Maura D.

AED 781 total

includes taxes & fees

12 Nov - 13 Nov

A bedroom with a wooden bed frame, a large window, and a painting of mountains on the wall.

4. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Hancock

patricia f.

AED 781 total

includes taxes & fees

12 Nov - 13 Nov

A bedroom with a large bed, two bedside tables, a painting, and a clock on the wall.

5. Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Hancock

Neil J.

AED 781 total

includes taxes & fees

12 Nov - 13 Nov

A cozy living room with a fireplace, leather sofa, and a television.

6. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Hancock

Ann

AED 781 total

includes taxes & fees

12 Nov - 13 Nov

A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

7. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Hancock

David

AED 781 total

includes taxes & fees

12 Nov - 13 Nov

A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

8. Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

Hancock

Eileen O.

AED 781 total

includes taxes & fees

12 Nov - 13 Nov

A row of multi-story buildings with a uniform architectural style, likely a hotel or resort, set against a backdrop of green hills and trees.

9. Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

Hancock

Dana

AED 781 total

includes taxes & fees

12 Nov - 13 Nov

A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

10. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Dalton

Marcia O.

AED 1,106 total

includes taxes & fees

12 Nov - 13 Nov

11. Berkshires Apartment at the Stephentown Hotel

Stephentown

Nicole O.

AED 725 total

includes taxes & fees

12 Nov - 13 Nov

A ski resort with multiple buildings and a crowd of people skiing.

12. 1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

Hancock

Thomas S.

AED 781 total

includes taxes & fees

12 Nov - 13 Nov

13. Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat

Hancock

shannon m.

AED 781 total

includes taxes & fees

12 Nov - 13 Nov

A bedroom with a Minecraft-themed bedspread, pillows, and wall decor.

14. Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

Hancock

Wendy D.

AED 781 total

includes taxes & fees

12 Nov - 13 Nov

15. Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Hancock

Kristina L.

AED 781 total

includes taxes & fees

12 Nov - 13 Nov

A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

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

New Lebanon

Joanna P.

AED 723 total

includes taxes & fees

16 Nov - 17 Nov

A bedroom with a bed, two bedside lamps, a window with curtains, and a wall with five framed paintings.

17. Ski On/Off Winter Mountain Suite Jiminy Peak-- Sleeps4- Home Away From Home

Hancock

Rony N.

AED 781 total

includes taxes & fees

12 Nov - 13 Nov

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

18. 1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

Hancock

Alyne K.

AED 781 total

includes taxes & fees

12 Nov - 13 Nov

19. Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Hancock

Shmaya G.

AED 1,087 total

includes taxes & fees

12 Nov - 13 Nov

20. Comfortable Berkshires retreat on mtn resort, SISO

Hancock

Amit

AED 1,800 total

includes taxes & fees

12 Nov - 13 Nov

View all properties

Find vacation rentals that suit your style

Top Lanesborough Hotel Reviews

A multi-story hotel with a classic facade, large windows, and a prominent entrance.

Hotel On North

Pittsfield

10/10 Excellent

The Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than the cookie cutter faux luxury I usually find in expensive hotels. The quirky design features such as vintage furniture and painted floors are a great juxtaposition to the perfect bed linens and...

Steve

Vacation Village in the Berkshires

Williamstown

10/10 Excellent

Anonymous traveler

Berkshire Mountain Lodge

Pittsfield

10/10 Excellent

Elliott

Two Adirondack chairs facing a river with a forested hill in the background.

The Yankee Inn

Lenox

10/10 Excellent

We had a fantastic stay at the Yankee! Our adjoining rooms were clean, large and comfortable. We loved that the rooms had a fireplace and balcony! All the amenities were appreciated. The breakfast had so many offerings, including fresh fruit and two kinds of eggs. The front desk staff (especially George) were professional, helpful and friendly. This was our first stay at the Yankee, but it won't be the last!

Colleen

A hotel patio with outdoor seating and a fire pit.

Hilton Garden Inn Lenox Pittsfield

Pittsfield

10/10 Excellent

A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

10/10 Excellent

Gregory

A bedroom with a bed, a television, a heater, and a door.

Williamstown Motel

Williamstown

10/10 Excellent

Grantley

A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

The Central Downtown Inn & Suites

Pittsfield

10/10 Excellent

Beautiful room, very conveniently located right next to a main strip of little shops, theaters and restaurants. We brought all of our own food and were able to store it safely, roomy refrigerator provided- and all cooking utensils, pots, pans, plates... Everything provided. There was a dvd player, and we were able to have movie nights, and a back balcony to enjoy coffee on the porch or read a book in a heavily wooded area which provided a nice shady view to block the parking lot. The front desk...

Anonymous traveler

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

Courtyard by Marriott Lenox Berkshires

Lenox

10/10 Excellent

Alyssa

A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

Berkshires Untold

Lenox

10/10 Excellent

High end feel at a budget friendly price. The room was boho fun but needs a few tweaks. I still give it 5 stars but wish that they had a variety of pillows on the bed, they were very nice but too thick for a stomach or back sleeper. There is a full mini bar with prices only available by QR reader, there is a free bottle of still water but since it was not marked i wasn’t sure what it was or if it was free. There is a fun wardrobe with robes but no place but the floor to put your suit case. Oh...

Jill

A garden with a swing set, a blue chair, and a flower bed.

Maple Terrace Motel

Williamstown

10/10 Excellent

Eric

A lodge with a large building and a dock by a lake, surrounded by forest.

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

10/10 Excellent

Sheila

A patio area with wooden chairs and tables, surrounded by dense greenery and trees.

Willows Motel Williamstown

Williamstown

10/10 Excellent

Sandra

A wooden cabin with a porch and steps leading to a door, surrounded by snow.

Jiminy Peak Mountain Resort

Hancock

10/10 Excellent

Lloyd A.

A large, two-story house with a front porch and a well-maintained garden with various flowers and shrubs.

Harbour House Inn

Cheshire

10/10 Excellent

Anonymous traveler

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?

Experience Three Sisters Sanctuary in Goshen, MA: This vacation home rental outside of Lanesborough is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay.

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?

Pontoosuc Lake and Mount Greylock State Reservation Visitor Center are a couple of lovely local spots to get outside and enjoy nature. While here, Mount Greylock State Reservation and Cheshire Reservoir are other places worth a visit.

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.

Lanesborough Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Lanesborough vacation rentals

1. Berkshire Mountain Lodge

2. Vacation Village in the Berkshires

3. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

4. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

5. Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

6. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

7. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

8. Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

9. Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

10. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

11. Berkshires Apartment at the Stephentown Hotel

12. 1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

13. Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat

14. Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

15. Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

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

17. Ski On/Off Winter Mountain Suite Jiminy Peak-- Sleeps4- Home Away From Home

18. 1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

19. Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

20. Comfortable Berkshires retreat on mtn resort, SISO

Find vacation rentals that suit your style

Top Lanesborough Hotel Reviews

Hotel On North

10/10 Excellent

Frequently Asked Questions

Can I find vacation rentals in Lanesborough?

What are some of the best vacation rentals in Lanesborough?

How many vacation rentals are there in Lanesborough?

What can I see and do in Lanesborough?

What are vacation rentals like in Lanesborough?