Photo by Caitlin Reese

Lanesborough vacation rentals

We found 368 vacation rentals — enter your dates for availability

Discover a selection of 11 homes and other vacation rentals in Lanesborough that are perfect for your trip. Whether you're going on vacation with family or friends, vacation rentals have the amenities you expect for your stay, including WiFi and parking. No matter what you're looking for, you'll be sure to find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Lanesborough

Showing deals for:Nov 14 - Nov 21

Image gallery for Woodland 5-BR Retreat 5-Min to Jiminy Peak

Pool
10 out of 10 rating
Exceptional
(8 reviews)

Woodland 5-BR Retreat 5-Min to Jiminy Peak

Pittsfield, MA

10% off
Price is CA $431
CA $4,132 total
includes taxes & fees
Woodland 5-BR Retreat 5-Min to Jiminy Peak

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

Find out more about Lanesborough

Find out more about Lanesborough

Delight in the lush landscape of Lanesborough

The forests and other outdoor surroundings create an inviting atmosphere in Lanesborough. Well-liked for its skiing, hiking and snowshoeing, this city is both romantic and scenic. Whether you're planning a family vacation, friends trip or romantic retreat, Vrbo has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Sightseeing in and around Lanesborough

Are you hoping to find attractions to visit while you're in the area? Venture out of your cozy vacation rental and experience everything that Lanesborough has to offer. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Jiminy Peak Mountain Resort (4.2 mi / 6.7 km)
  • Bousquet Ski Area (7.5 mi / 12.1 km)
  • Waubeeka Golf Links (9.7 mi / 15.6 km)
  • Kennedy Park (9.8 mi / 15.8 km)
  • Furnace Brook Winery at Hilltop Orchards (11.6 mi / 18.7 km)
  • Wood's Pond (11.8 mi / 19 km)

Exploring the natural features in Lanesborough

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Lanesborough is a great place to get outside. These are some of the area's noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Mount Greylock State Reservation Visitor Center (2.6 mi / 4.3 km)
  • Brodie Mountain (8.2 mi / 13.2 km)
  • Mount Greylock (8.9 mi / 14.3 km)
  • Mount Greylock State Reservation (8.9 mi / 14.4 km)
  • Lenox Mountain (8.9 mi / 14.4 km)
  • Pleasant Valley Wilderness Sanctuary (9.3 mi / 15 km)

Transportation options to and around Lanesborough

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 7.1 mi (11.5 km) from the city center. If you're unable to find a flight that fits your schedule, you might consider flying into Hudson, NY (HCC-Columbia County), which is 29.1 mi (46.9 km) away.

Frequently asked questions

What is the best area to stay in Lanesborough when booking a vacation rental?
When considering a vacation rental in Lanesborough, Massachusetts, the area around Pontoosuc Lake is an excellent choice. This picturesque neighbourhood not only offers stunning views of the lake but also provides easy access to outdoor activities such as fishing, boating, and hiking. The tranquil atmosphere makes it ideal for a relaxing getaway while still being close to local attractions.

Another appealing area is the vicinity of the Berkshire Museum in nearby Pittsfield, which is just a short drive away. This museum showcases a diverse range of exhibits, from art to natural history, and is great for families or anyone interested in culture. Staying here allows you to enjoy the vibrant arts scene of the Berkshires, with various galleries and theatres within reach.
How much does it cost to rent a vacation home in Lanesborough?
Prices for vacation rentals in Lanesborough vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Lanesborough to more spacious homes.
Are there any discounts for Lanesborough vacation house rentals?
You can find great discounts on house rentals in Lanesborough on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best Lanesborough ski resort rentals?
For ski resort rentals near Lanesborough, Massachusetts, the closest ski area is Jiminy Peak, located just a short drive away. In the Lanesborough area, travellers can explore a variety of rental options that cater to both winter sports enthusiasts and those looking to enjoy the scenic beauty of the Berkshires.

Properties in nearby areas such as Hancock or Pittsfield offer a selection of vacation homes and cabins, many of which come equipped with amenities like full kitchens, spacious living areas, and outdoor decks for enjoying the crisp mountain air. Some rentals may also feature wood-burning stoves or fireplaces, great for unwinding after a day on the slopes.
What is the most popular type of vacation rental accomodation in Lanesborough?
In Lanesborough, vacation houses are the most popular type of rental, with about 11 available in the area. These homes often come equipped with multiple bedrooms, full kitchens, and spacious living areas, making them ideal for families or groups. In addition to vacation houses, there are several cottages, apartments, and condos, which offer diverse options for visitors. Cottages typically provide a charming, rustic feel, while apartments and condos might focus on modern comforts with amenities like laundry facilities and shared leisure areas.
Are there any family house rentals in Lanesborough?
In Lanesborough, Massachusetts, there are numerous family-friendly house rentals available, with around 16 options to choose from. The area is well-known for its beautiful natural surroundings and proximity to outdoor activities, making it an ideal spot for families. Many of these properties feature spacious living areas, fully equipped kitchens, and outdoor spaces where children can play safely. Visitors can also expect amenities such as Wi-Fi and laundry facilities, ensuring a comfortable stay.
Can I rent a vacation home with a pool or hot tub in Lanesborough?
In Lanesborough, Massachusetts, there are several vacation homes available for rent that feature pools and hot tubs, suiting travellers seeking relaxation and leisure. The area is known for its picturesque landscapes and proximity to attractions such as the Berkshire Mountains, making it an appealing destination for a getaway.
Can I find long-stay vacation rentals in Lanesborough?
A long-stay vacation rental in Lanesborough is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Lanesborough?
In Lanesborough, there are several pet-friendly house rentals available, making it a great destination for travellers looking to bring their furry companions along. Many of these properties offer spacious living areas, fully equipped kitchens, and outdoor spaces where pets can enjoy the fresh air.

The rentals are often situated near the beautiful nature trails of the nearby Berkshire Mountains, providing ample opportunities for outdoor adventures with pets, such as hiking and exploring. Additionally, Lanesborough is close to scenic spots like the beautiful Pontoosuc Lake, where pet owners can enjoy leisurely walks around the water.
Are there any remote work vacation rentals in Lanesborough?
In Lanesborough, Massachusetts, there are numerous remote work vacation rentals available, with around 16 options for travellers seeking a productive getaway. The area is renowned for its picturesque landscapes and proximity to outdoor activities, making it an ideal backdrop for those blending work and leisure.

Many of the properties come equipped with essential amenities for remote work, such as desks, Wi-Fi, and comfortable office spaces, including monitors and ergonomic chairs. This setup allows guests to maintain productivity while enjoying the serene surroundings. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Lanesborough vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Lanesborough with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Lanesborough?
In Lanesborough, popular vacation rental amenities typically include fully equipped kitchens, which are essential for preparing meals during your stay. Most properties come with refrigerators, stovetops, cookware, dishware, and utensils, making it convenient for guests to enjoy home-cooked meals. Additionally, many rentals offer microwaves, providing an extra level of convenience for quick snacks or reheating leftovers.
When is the best time to visit Lanesborough for a vacation rental?
The best time to visit Lanesborough for a vacation rental is during the vibrant summer months of June to August. This peak season attracts a diverse crowd of adventure seekers and families looking to enjoy the lush landscapes and numerous outdoor activities available in the area. With temperatures typically ranging from the mid-teens to low 30s Celsius, it's an ideal backdrop for hiking, biking, and exploring the scenic beauty of the Berkshires.

July stands out as the most popular month, where you can immerse yourself in a lively atmosphere filled with fellow travellers. The region offers a wealth of attractions, from the stunning Mount Greylock to the picturesque lakes great for swimming and kayaking. You'll also find local festivals and events that bring the community together, making for a memorable experience.

If you're looking for a more budget-friendly option, consider visiting in December. While this month is less crowded, it still offers a unique charm with winter activities like snowshoeing and cross-country skiing. Plus, the vacation season brings a festive spirit to the area, great for those who enjoy a quieter, more reflective vacation experience.
How early should I book a Lanesborough vacation rental?
Book your Lanesborough vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Lanesborough home rental booking on Vrbo?
To find Lanesborough vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Lanesborough vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

More Vacation Rentals ideas

East Sandwich Vacation Rentals
Standard Link for East Sandwich
Barnstable Vacation Rentals
Standard Link for Barnstable
Rockport Vacation Rentals
Standard Link for Rockport
Worcester Vacation Rentals
Standard Link for Worcester
Plymouth Vacation Rentals
Standard Link for Plymouth
Chatham Vacation Rentals
Standard Link for Chatham
Eastham Vacation Rentals
Standard Link for Eastham
Oak Bluffs Vacation Rentals
Standard Link for Oak Bluffs
Marlborough Vacation Rentals
Standard Link for Marlborough
Falmouth Vacation Rentals
Standard Link for Falmouth
Orleans Vacation Rentals
Standard Link for Orleans
Wellfleet Vacation Rentals
Standard Link for Wellfleet
Great Barrington Vacation Rentals
Standard Link for Great Barrington
Truro Vacation Rentals
Standard Link for Truro
Manchester-by-the-Sea Vacation Rentals
Standard Link for Manchester-by-the-Sea
Sandwich Vacation Rentals
Standard Link for Sandwich
North Truro Vacation Rentals
Standard Link for North Truro
Hyannis Vacation Rentals
Standard Link for Hyannis
Provincetown Vacation Rentals
Standard Link for Provincetown
Dennis Vacation Rentals
Standard Link for Dennis
North Andover Vacation Rentals
Standard Link for North Andover
Gloucester Vacation Rentals
Standard Link for Gloucester
Nantucket Vacation Rentals
Standard Link for Nantucket
Brewster Vacation Rentals
Standard Link for Brewster
Mashpee Vacation Rentals
Standard Link for Mashpee
Dennis Port Vacation Rentals
Standard Link for Dennis Port
New Bedford Vacation Rentals
Standard Link for New Bedford
Woods Hole Vacation Rentals
Standard Link for Woods Hole

People also search for

Nantucket Cottages
Standard Link for Nantucket
Truro Cottages
Standard Link for Truro