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Lanesborough Holiday Rentals

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Holiday Rentals in Lanesborough

Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2093)
"Great place!"
United States
Nicole
The price is AU$174
includes taxes & fees
2 Nov - 3 Nov
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (983)
"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 AU$240
includes taxes & fees
26 Oct - 27 Oct
Jiminy Peak Mountain Resort
Florida Mountain Log Cabin!
2.0 star property
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is AU$631
includes taxes & fees
23 Oct - 24 Oct
Florida Mountain Log Cabin!
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AU$586
includes taxes & fees
28 Oct - 29 Oct
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
9.6 out of 10, Exceptional, (8)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is AU$611
includes taxes & fees
27 Oct - 28 Oct
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Charming 2-bedroom house in beautiful countryside of Cummington, Ma
2.0 star property
The price is AU$442
includes taxes & fees
23 Oct - 24 Oct
Charming 2-bedroom house in beautiful countryside of Cummington, Ma
The Greylock Cabin - True Cabin in the woods on 30 acres. Pet-Friendly
10.0 out of 10, Exceptional, (3)
"Wonderful view, peaceful quiet area, cosy cabin."
United States
Anonymous traveller
The price is AU$687
includes taxes & fees
28 Oct - 29 Oct
The Greylock Cabin - True Cabin in the woods on 30 acres. Pet-Friendly
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
9.8 out of 10, Exceptional, (33)
"Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay"
United States
Lindsey E.
The price is AU$707
includes taxes & fees
23 Oct - 24 Oct
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Downtown | Waterfront | Walk to Shops
10.0 out of 10, Exceptional, (6)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is AU$427
includes taxes & fees
23 Oct - 24 Oct
Downtown | Waterfront | Walk to Shops
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
10.0 out of 10, Exceptional, (8)
"Great location. Howie is very communicative. Wish we could have stayed longer. "
United States
Una D.
The price is AU$376
includes taxes & fees
28 Oct - 29 Oct
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Bear Creek Cabin
10.0 out of 10, Exceptional, (41)
"We enjoyed our stay!!"
United States
Hillary S.
The price is AU$928
includes taxes & fees
23 Oct - 24 Oct
Bear Creek Cabin
2-Bdr Apt In Town, By the Water
9.4 out of 10, Exceptional, (9)
"Lovely property, in good shape. Close to many Williamstown attractions."
United States
Scott M.
The price is AU$419
includes taxes & fees
4 Nov - 5 Nov
2-Bdr Apt In Town, By the Water
UNIQUE - 1BR Country Condo @ Jiminy Peak
10.0 out of 10, Exceptional, (14)
"Clean and quiet, nicely decorated! "
United States
Robert
The price is AU$485
includes taxes & fees
24 Oct - 25 Oct
UNIQUE - 1BR Country Condo @ Jiminy Peak
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
10.0 out of 10, Exceptional, (4)
"It was great experience and we loved the ammenities."
United States
Carrie C.
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
10.0 out of 10, Exceptional, (3)
"We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!"
United States
Jen B.
The price is AU$376
includes taxes & fees
28 Oct - 29 Oct
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
10.0 out of 10, Exceptional, (23)
"This property is spacious, clean and well- appointed. I would stay here again!"
United States
Amanda M.
The price is AU$376
includes taxes & fees
28 Oct - 29 Oct
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Bungalow in the Berkshires
10.0 out of 10, Exceptional, (3)
"We had a lovely stay. Easy check in and communication was great. "
United States
Dale G.
The price is AU$650
includes taxes & fees
23 Oct - 24 Oct
Bungalow in the Berkshires
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
9.4 out of 10, Exceptional, (16)
"We absolutely enjoyed this pleasant apartment. Its within the walking distance from the ski lifts which was perfect for all of us including 5 year old kid. "
United States
Janja
The price is AU$374
includes taxes & fees
29 Oct - 30 Oct
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Taborton Harvest Boulder Pines Cabin in the woods
10.0 out of 10, Exceptional, (12)
"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 AU$286
includes taxes & fees
28 Oct - 29 Oct
Taborton Harvest Boulder Pines Cabin in the woods
Comfortable Berkshires retreat on mtn resort, SISO
8.8 out of 10, Excellent, (6)
"Kind and responsive host."
United States
Javier
The price is AU$761
includes taxes & fees
23 Oct - 24 Oct
Comfortable Berkshires retreat on mtn resort, SISO
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

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, 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 favourite 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 depend 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 AU$174 per night. Entering your travel dates in the search wizard might find you 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?

Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water": This holiday home rental outside of Lanesborough is located on a river, and offers a fireplace, laundry facilities and free WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities such as a stovetop and a microwave can make your holiday run smoothly.

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?

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 Barrington Stage Company.

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.