Lanesborough holiday homes

We found 318 holiday rentals — enter your dates for availability
Discover a selection of 11 homes and other holiday rentals in Lanesborough that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday rentals have the amenities that you need and want for your stay, which might include Wi-Fi and a fireplace. At the end of the day, you'll find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Lanesborough

Showing deals for:18 Dec - 25 Dec

Workstation with a view!
view from the 2nd bedroom
Open plan dining area with water views and access to the sunroom
View of the lower deck from the sunroom
Exceptional
(65 reviews)

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield

8% off
NZ$9,935
for 7 nights, 1 home
NZ$1,419 per night
includes taxes & fees
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Interior
Living area
Interior
Outdoor dining
Exceptional
(35 reviews)

Renovated Pittsfield Colonial by Evergreen Home

Pittsfield

11% off
NZ$7,822
for 7 nights, 1 home
NZ$1,117 per night
includes taxes & fees
Renovated Pittsfield Colonial by Evergreen Home
Reading nook with natural lighting
Fully screened porch!
Dining Room w/ Doors to Screened Porch Dining Area
Front Staircase
Exceptional
(8 reviews)

Berkshires Colonial on 2 Acres by Evergreen Home

Richmond

12% off
NZ$6,383
for 7 nights, 1 home
NZ$912 per night
includes taxes & fees
Berkshires Colonial on 2 Acres by Evergreen Home
Dining
Terrace/patio
Private kitchen
Room
Exceptional
(20 reviews)

Family-friendly, private three bedroom cottage in the beautiful Berkshires

Williamstown

12% off
NZ$5,107
for 7 nights, 1 cottage
NZ$730 per night
includes taxes & fees
Family-friendly, private three bedroom cottage in the beautiful Berkshires
Living area
Interior
Interior
Room
Exceptional
(41 reviews)

A MAGIC SPOT: Booking all year. A perfect, private, quiet mountaintop location.

Stephentown

8% off
NZ$2,920
for 7 nights, 1 home
NZ$417 per night
includes taxes & fees
A MAGIC SPOT: Booking all year. A perfect, private, quiet mountaintop location.
Renovated kitchen
Outdoor dining
Interior
Property grounds
Exceptional
(39 reviews)

Large, family-friendly farmhouse located in the beautiful Berkshires

Williamstown

20% off
NZ$6,769
for 7 nights, 1 home
NZ$967 per night
includes taxes & fees
Large, family-friendly farmhouse located in the beautiful Berkshires
Entrance into house with wood burning stove to right and staircase
View from 2nd floor balcony (after leaves have fallen)
Large Smart HDTV with electric fireplace in living room, showing dining room
Views from the back of the 16 acres on the property
Exceptional
(73 reviews)

2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

Williamstown

12% off
NZ$4,183
for 7 nights, 1 home
NZ$598 per night
includes taxes & fees
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
View from ski room to trail thru woods to Grouse Run - fantastic location!!
Spring at Jiminy Peak 2019
Country Inn heated pool & outdoor hot tub is open all year. Towels are provided
Interior
Exceptional
(46 reviews)

Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.

Hancock

13% off
NZ$15,486
for 7 nights, 1 home
NZ$2,212 per night
includes taxes & fees
Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
kitchen and laundry room area
new backyard table
another view of kitchen
Beaver Pond Pool/clubhouse
Exceptional
(17 reviews)

3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY

Lanesborough

22% off
NZ$6,253
for 7 nights, 1 apartment
NZ$893 per night
includes taxes & fees
3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
Interior
Dining
view into large bathroom
Living Room, wow!
Exceptional
(17 reviews)

New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.

Richmond

17% off
NZ$4,267
for 7 nights, 1 apartment
NZ$610 per night
includes taxes & fees
New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.
Interior
Interior
Bathroom
Property grounds
Exceptional
(6 reviews)

Historic Stone Church in The Berkshires

Lanesborough

8% off
NZ$4,786
for 7 nights, 1 home
NZ$684 per night
includes taxes & fees
Historic Stone Church in The Berkshires

  • 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, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Delight in the lush landscape of Lanesborough

The forests and other outdoor surroundings create an inviting atmosphere in Lanesborough. Revered for its skiing, hiking and snowshoeing, this city is both romantic and scenic. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday 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 during your stay? Venture out of your holiday home and experience everything that makes Lanesborough a one-of-a-kind holiday spot. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Wyndhurst Golf & Club (12.2 mi / 19.6 km)
  • Zema's Nursery (7.9 mi / 12.8 km)
  • Balderdash Cellars (8.9 mi / 14.3 km)

Exploring the natural features in Lanesborough

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Lanesborough is a great place to get out in nature. These are some of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Pontoosuc Lake (1.8 mi / 2.9 km)
  • Mount Greylock State Reservation Visitor Center (2.6 mi / 4.3 km)
  • Wahconah Falls State Park (6.2 mi / 9.9 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)

Transport 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 centre. If you can't find a flight that's convenient for your trip, you could also fly 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 holiday rental?
When considering a holiday rental in Lanesborough, Massachusetts, a popular area to stay is near the picturesque Berkshire Mountains. This region offers a delightful blend of natural beauty and charming local attractions, making it a superb getaway. The neighbourhood boasts a variety of properties, suiting different tastes and budgets, ensuring that visitors can find something that suits their needs.Staying in this area allows easy access to beautiful outdoor spaces, such as the nearby Lake Pontoosuc, where you can enjoy activities like kayaking and fishing. Additionally, the famous Berkshire Museum is not too far away, offering fascinating exhibits that appeal to art and history enthusiasts alike.
Where are the best Lanesborough ski resort rentals?
For the best ski resort rentals near Lanesborough, Massachusetts, travellers should explore options in the nearby town of Pittsfield, which is only a short drive away from the slopes of Jiminy Peak. This area offers a variety of rental accommodations, including cosy cabins and spacious condos, many of which come equipped with amenities such as fully stocked kitchens, fireplaces, and sometimes even hot tubs for après-ski relaxation.The properties in Pittsfield often provide easy access to local dining and shopping, enhancing the overall experience for visitors. Additionally, rentals in the nearby town of Williamstown may offer a more quaint, rural atmosphere, with charming homes that feature outdoor spaces, great for enjoying the picturesque landscapes of the Berkshires.For those seeking outdoor activities beyond skiing, the region offers hiking trails in the summer and beautiful autumn foliage in the fall.
What is the most popular type of holiday rental accomodation in Lanesborough?
In Lanesborough, holiday houses are the most popular type of holiday rental, with around 30 available throughout the area. These properties typically offer spacious living areas, multiple bedrooms, and fully equipped kitchens, making them ideal for families or larger groups. Many also feature outdoor spaces like gardens or patios where guests can relax and enjoy the serene surroundings. Additionally, there are several cottages, condos, and apartments in the vicinity, providing a variety of options for different preferences.
Are there any family house rentals in Lanesborough?
In Lanesborough, Massachusetts, there are 14 family-friendly house rentals available, making it a great choice for those travelling with children. The area is known for its scenic beauty, located in the Berkshires, and offers a range of properties ideal for families. Many of these homes come equipped with spacious living rooms, full kitchens for preparing meals together, and outdoor areas where children can play and explore.Visitors can enjoy nearby attractions such as the picturesque Berkshire Botanical Garden and the historic Mount Greylock State Reservation, superb for hiking and outdoor activities. Additionally, families can relax in amenities like game rooms, private patios, and BBQ facilities, ensuring a comfortable and enjoyable stay for all ages.
Can I rent a holiday home with a pool or hot tub in Lanesborough?
In Lanesborough, Massachusetts, there are several holiday homes available for rent that feature pools and hot tubs. This charming town, located in the scenic Berkshires, offers a tranquil setting for visitors. Many of these properties come with amenities such as private pools, hot tubs, spacious outdoor areas, and fully equipped kitchens, making them ideal for families or groups seeking relaxation and recreation.Travellers can enjoy the natural beauty of the area, with opportunities for hiking, biking, and exploring nearby attractions like the picturesque Berkshire Mountains and local cultural events.
Are there pet-friendly house rentals in Lanesborough?
In Lanesborough, Massachusetts, there are several pet-friendly house rentals available for those travelling with their furry companions. Many of these properties offer amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces where pets can roam freely. The scenic Berkshire region provides a beautiful backdrop, making it an ideal location for outdoor enthusiasts and pet owners alike.Within close proximity, visitors can explore various parks and nature trails, superb for walks with pets. The nearby Mount Greylock State Reservation offers hiking opportunities with stunning views and is a fantastic spot to enjoy nature.
Are there any remote work holiday rentals in Lanesborough?
In Lanesborough, Massachusetts, there are numerous remote work-friendly holiday rentals available, with around 42 options to choose from. This charming town, situated in the Berkshires, provides a peaceful backdrop for those looking to blend work and leisure. Many of the properties come equipped with dedicated workspaces such as desks and office chairs, allowing for a comfortable and productive environment.Travellers can expect amenities that enhance their stay, including Wi-Fi for seamless connectivity, comfortable living areas for relaxation, and kitchens for preparing meals. The scenic surroundings also offer opportunities for outdoor activities during breaks, such as hiking in nearby parks or visiting local attractions like the Berkshire Museum. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Lanesborough?
In Lanesborough, popular holiday rental amenities include fully equipped kitchens, allowing guests to prepare their own meals during their stay. Many properties also feature decks or patios, providing a lovely outdoor space to relax or enjoy a morning coffee. Onsite parking is commonly available, making it convenient for travellers with vehicles. Additionally, rentals often come with useful appliances such as blenders and coffee or tea makers, enhancing the overall comfort and convenience for guests.
When is the best time to visit Lanesborough for a holiday rental?
The best time to visit Lanesborough for a holiday rental is during the peak season from June to August. This vibrant period attracts visitors seeking outdoor adventures, cultural experiences, and a chance to enjoy the beautiful landscapes of the Berkshires. With warm temperatures typically ranging from 20 to 30 degrees Celsius, it's an ideal time for hiking, biking, and exploring the many local attractions, including the stunning Mount Greylock State Reservation.July stands out as the most popular month, bustling with activity and offering a lively option. You can partake in various events, art festivals, and outdoor activities that showcase the region's charm and community spirit. The long, sunny days provide ample opportunities for sightseeing and enjoying the area's natural beauty, making it a great time for travellers.For those looking for a more budget-friendly option, consider planning your visit in December. While this month is quieter, it presents a unique opportunity to experience Lanesborough's winter wonderland, great for cozy retreats and enjoying the festive season. The serene atmosphere allows for peaceful walks and the chance to indulge in local winter activities.Ultimately, the choice of when to visit Lanesborough hinges on your preference for a bustling summer experience filled with outdoor fun or a tranquil winter getaway that offers a different kind of charm.
What are the top attractions in Lanesborough?
In Lanesborough, Massachusetts, visitors can enjoy a range of scenic attractions that highlight the natural beauty of the area. The nearby Mount Greylock State Reservation offers stunning hiking trails, breathtaking views from the summit, and opportunities for outdoor activities like biking and birdwatching. The reservation is the highest point in Massachusetts, making it a popular spot for hikers and nature enthusiasts.Additionally, the Berkshire Museum in nearby Pittsfield showcases art, history, and nature exhibits, providing a cultural experience for those interested in the local heritage. Lanesborough is also close to the picturesque Pontoosuc Lake, ideal for kayaking, fishing, and enjoying a relaxing day by the water.For a taste of local arts and crafts, visitors can explore the charming towns of the Berkshires, which are known for their vibrant arts scene and numerous galleries.
Are all fees included in the Lanesborough holiday homes prices shown on Bookabach?
Bookabach 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.
Are there any Lanesborough holiday homes with parking?
Bookabach offers a wide selection of holiday homes 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 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.
Are there any discounts for Lanesborough holiday homes?
You can find great discounts on holiday homes in Lanesborough on Bookabach, 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.
Can I change or cancel my Lanesborough holiday home booking on Bookabach?
To find Lanesborough holiday rentals with free cancellation, just use Bookabach'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". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Lanesborough?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Lanesborough holiday home?
Book your Lanesborough holiday home 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 Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Lanesborough?
Prices for holiday homes 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. Bookabach offers something for every taste and budget, from affordable homes in Lanesborough to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach 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, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.