A tower with a green glass dome and intricate carvings.

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Lanesborough holiday rentals

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

1. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,685 reviews)
"Love this place for a weekend getaway."
United States
Jacob
The price is £89
includes taxes & fees
30 Sept - 1 Oct
Vacation Village in the Berkshires
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,160 reviews)
"Absolutely wonderful room with many amenities with short drive to Tanglewood and restaurant options."
United States
Jay
The price is £84
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge
A snow-covered outdoor area with a fire pit, tables, and chairs.

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

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"Loved this spot. Beautiful view of the mountain. Beyond easy checkin and check out process. Everything you need is on the mountain - we didnt have to leave all weekend. Highly recommend! "
United States
Maura D.
The price is £172
includes taxes & fees
29 Sept - 30 Sept
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
A rustic wooden interior with various stalls selling items like books, snacks, and wine.

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

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"The apartment itself is very clean and perfect for what we needed - a quick 2 night stay. The pool, hot tub and Jiminy Peak right there was great. Howie, the owner, was excellent with communication. Not his fault, the Country Inn itself is a bit outdated yet front desk assistants were so nice and friendly."
United States
Ann
The price is £172
includes taxes & fees
30 Sept - 1 Oct
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
A rustic wooden interior with shelves stocked with various products, a 'Tree-Free' sign, and a section with bottled beverages.

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

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (3 reviews)
"Stayed one night at one of my favorite ski spots. Will be back again!"
United States
Neil J.
The price is £169
includes taxes & fees
29 Sept - 30 Sept
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Four people seated at a table with food and drinks, wearing winter sports helmets.

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

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Hancock
9.8 out of 10, Exceptional, (9 reviews)
"A great, comfy suite! We had a great stay! "
United States
Wendy D.
The price is £169
includes taxes & fees
29 Sept - 30 Sept
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

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

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Hancock
9.8 out of 10, Exceptional, (25 reviews)
"We stayed here twice this season and it was wonderful. The unit was clean, conveniently located and was fully equipped with all the essentials, making our stay comfortable and seamless from start to finish. We will definitely be back!"
United States
Kristina L.
The price is £169
includes taxes & fees
29 Sept - 30 Sept
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

8. 1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Hancock
9.4 out of 10, Exceptional, (6 reviews)
"Convenience to slopes and restaurants really great….,had a nice stay"
United States
Thomas S.
The price is £172
includes taxes & fees
29 Sept - 30 Sept
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

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

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Hancock
9.4 out of 10, Exceptional, (18 reviews)
"Nice Place"
United States
Tom C.
The price is £169
includes taxes & fees
29 Sept - 30 Sept
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
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

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Dalton
9.8 out of 10, Exceptional, (33 reviews)
"We were on a girls backpacking trip and this was the perfect location right off the trail to clean up, get some great rest and grab dinner. The people are so friendly in Dalton and this place had everything we needed!"
United States
Allie T.
The price is £268
includes taxes & fees
8 Oct - 9 Oct
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
A large building with a covered entrance and multiple windows, surrounded by snow-covered ground and parked cars.

11. WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Hancock
8.6 out of 10, Excellent, (18 reviews)
"Great stay! Perfect location by the pool and nicely renovated as advertised!"
United States
Matthew B.
The price is £169
includes taxes & fees
29 Sept - 30 Sept
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

12. 2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Hancock
9.8 out of 10, Exceptional, (6 reviews)
"Excellent communication with our host and property exactly as described. Easy check in/check out."
United States
Jillian G.
The price is £249
includes taxes & fees
1 Oct - 2 Oct
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Pool

13. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very good, (10 reviews)
"The owner was responsive. The heater worked well. The living spaces are as advertised. Traveling with 5 adults and a toddler; the layout is great. Convenient location for day trips and hiking."
United States
Maura L.
The price is £410
includes taxes & fees
2 Oct - 3 Oct
Comfortable Berkshires retreat on mtn resort, SISO
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

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

Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Hancock
9.6 out of 10, Exceptional, (33 reviews)
"The suite was a great. Comfortable, clean and decorated very nicely. Bed was very comfortable with nice linens and pillows. "
United States
Eileen O.
The price is £169
includes taxes & fees
29 Sept - 30 Sept
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

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

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"Awesome location went for a solo trip w the purpose of spending time alone in nature with myself and god got exactly that calm quiet beautiful scenic area great room and service would book again"
United States
Varun M.
The price is £161
includes taxes & fees
29 Sept - 30 Sept
NEW RENO - Chalet-style farm loft near Tanglewood
A living room with a sofa, armchairs, a TV, a fireplace, and a large window.

16. Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views

Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
Hancock
8.0 out of 10, Very good, (1 review)
"I chose this place at the very last minute. It was all that I expected and wanted and more: two bedrooms with three beds, a comfortable living space, two full bathrooms, kitchen with all the basic necessities, TV in each bedroom and in the living room, a dining table and chairs, an outside porch with table, a big open space, and grill, easy parking and access, quiet, .and access to two pools. The place was well tended: clean, with towels and extras blankets ready. Howard, the owner, checked on...
United States
Cecilia S.
The price is £278
includes taxes & fees
27 Oct - 28 Oct
Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
A Country Inn with a large, welcoming entrance and multiple parking spaces.

17. 1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Hancock
8.8 out of 10, Excellent, (8 reviews)
"Everything was wonderful…"
United States
Alyne K.
The price is £169
includes taxes & fees
29 Sept - 30 Sept
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
A wooden deck with a table and chairs, surrounded by a white railing.

18. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
8.4 out of 10, Very good, (10 reviews)
"Very comfortable and clean accommodations in a nice neighborhood, and a great deck to appreciate the view."
United States
Stephen L.
The price is £409
includes taxes & fees
13 Oct - 14 Oct
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
A lakeside picnic area with a bench and umbrella, surrounded by autumn-colored trees.

19. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (39 reviews)
"The house was very clean! The hot tub was great! From checking in and checking out the host made everything so easy. We will definitely stay again!"
United States
Kyle R.
The price is £322
includes taxes & fees
29 Sept - 30 Sept
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
A spacious living room with a wooden floor, a sofa, a coffee table, and a lamp. There is a dining area in the background with a table and chairs.

20. Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.6 out of 10, Exceptional, (15 reviews)
"Our stay was beautiful! The check in process was super easy and the building was easy to access. The apartment was very clean and it was a lovely stay."
United States
Margaret C.
The price is £211
includes taxes & fees
1 Oct - 2 Oct
Penthouse Apartment on Park Street
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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Top Lanesborough Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"This was a nice clean convenient hidden gem. Situated on the water, a little cool right now , but the beginning of fall follege was very pretty. Staff was polite and helpful. I would return."
Anthony 2-night trip
Posted less than an hour ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Find out more about Lanesborough

Everything you need to know about Lanesborough holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Lanesborough holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Lanesborough holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Lanesborough holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Lanesborough. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Lanesborough holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Lanesborough holiday rentals we have selected for you start as low as £84 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Lanesborough rentals

At Expedia, we put the best Lanesborough holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Lanesborough rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Lanesborough holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Lanesborough. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Experience Three Sisters Sanctuary in Goshen, MA: This holiday 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 holiday rentals are there in Lanesborough?

Choose from 11 Expedia holiday rentals in Lanesborough for a memorable holiday.

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 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.