Lanesborough vacation rentals

We found 341 vacation rentals — enter your dates for availability

Discover a selection of 10 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:Jun 12 - Jun 19

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

Front of house - spring
10 out of 10, Exceptional, (44 reviews)
Exceptional
(44 reviews)

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

Hancock

13% off
Price is $740
$5,180 for 7 nights
All fees included
Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.

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Find out more about Lanesborough

Why visit Lanesborough

  • Outdoor adventures: Lanesborough is a haven for outdoor enthusiasts, offering skiing, hiking, and stunning nature reserves.
  • Scenic beauty: Nestled in the Berkshires, the area is known for its picturesque mountains and breathtaking landscapes.
  • Historic charm: Explore local history through charming historic houses and quaint shopping centers.
  • Variety of accommodations: Choose from cozy vacation homes, comfortable condos, or charming cabins that suit every budget.
  • Family-friendly activities: Lanesborough offers numerous attractions perfect for families, ensuring a memorable vacation experience.

Popular types of accommodation in Lanesborough

If you're planning a getaway to Lanesborough, you'll find a variety of popular vacation rentals to suit your needs. Choose from cozy houses, comfortable condos, or charming cabins. Whether you're seeking family-friendly options or a vacation home with breakfast included, Lanesborough has something for everyone. Discover the perfect Massachusetts vacation rental for your next adventure.

  • Houses: These spacious homes are the top choice for travelers seeking comfort and privacy during their stay in Lanesborough, perfect for families or groups.
  • Condos: A popular option, condos offer modern amenities and a convenient location, ideal for those wanting both comfort and accessibility.
  • Cabins: Experience the charm of nature with cozy cabins that provide a rustic escape amidst the beautiful landscapes.
  • Cottages: Quaint and inviting, cottages are perfect for a romantic getaway or a peaceful retreat.
  • Apartments: For a more urban feel, apartments provide a comfortable and practical stay close to local attractions.**

Top attractions near Lanesborough

Lanesborough, Massachusetts, is a fantastic destination for outdoor enthusiasts and adventure seekers. With its stunning nature reserves, picturesque mountains, and historic houses, the area offers a variety of attractions for travelers looking to immerse themselves in culture and adventure. Whether you're hitting the slopes or exploring the local history, Lanesborough has something for everyone, making it an ideal spot for a memorable vacation.

  • Mount Greylock: A stunning mountain located 9 miles from Lanesborough, Mount Greylock offers breathtaking views and outdoor adventures. Hike its trails to experience the beauty of nature, especially in the fall when foliage bursts with color.
  • Hancock Shaker Village: Situated 8 miles away, this historic village immerses you in Shaker culture. Explore restored buildings, beautiful gardens, and learn about the Shaker way of life through engaging exhibits.
  • The Clark Art Institute: Located 13 miles from Lanesborough, this renowned art center features an impressive collection of American and European masterpieces, surrounded by serene landscapes perfect for contemplation.

Things to do recommended for couples

Experience romance in Lanesborough, Massachusetts, by exploring the scenic Berkshire Mountains. Enjoy a cozy picnic at the beautiful Lake Pontoosuc or take a leisurely hike on the nearby trails. Don't miss the stunning sunset views—a perfect backdrop for a memorable couple's getaway.

Things to do recommended for families

Families will love exploring the scenic beauty of the Berkshire Mountains, enjoying a day at the nearby Jiminy Peak Mountain Resort for outdoor activities, or visiting the charming local shops and restaurants in Lanesborough for a taste of the area’s culture.

Things to do recommended for groups

Groups in Lanesborough can hike the scenic trails of the nearby Mount Greylock State Reservation, enjoy a wine tasting at a local vineyard, and experience the charm of the Berkshire Botanical Garden. Don't miss the vibrant art scene at local galleries for a creative touch to your trip.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Lanesborough

When planning your trip—whether you’re traveling with friends, family, pets, or seeking extended stays—be sure to prioritize the right filters for your needs. Here are some helpful booking tips for Vrbo.

  • Traveling to Lanesborough with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor space for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Lanesborough with young kids: Traveling with young kids can be a bit tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you'll be to family-friendly attractions.
  • Taking your pets with you to Lanesborough: For many families, a getaway wouldn’t feel complete without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Lanesborough: If you’re searching for vacation rentals with special offers for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don’t forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Lanesborough

Discover the charm of Lanesborough, Massachusetts, a perfect destination for outdoor enthusiasts and families alike. Nestled in the beautiful Berkshires, this city offers skiing adventures and stunning scenery. Nearby, explore quaint shopping centers and cozy hunting lodges, all while enjoying a romantic or budget-friendly atmosphere. Whether you're looking for family-friendly activities or a peaceful retreat, Lanesborough and its surroundings promise a memorable vacation experience.

  • Lenox: Located 11 miles from Lanesborough, Lenox is a charming city that attracts visitors seeking a blend of entertainment and culture. Known for its romantic ambiance, Lenox is home to the famous Tanglewood Music Festival, where you can enjoy concerts in a picturesque outdoor setting. The city also features beautiful lakes and scenic mountains, perfect for hiking and outdoor adventures. In the winter, skiing enthusiasts can take advantage of nearby ski resorts, making it a year-round destination for leisure and recreation.
  • Pittsfield: Just 5 miles from Lanesborough, Pittsfield is an exciting city that offers a wealth of adventure and sports activities. This vibrant locale is known for its ski fields and resorts, providing ample opportunities for winter sports lovers. In addition to skiing, visitors can explore the scenic lakes and mountains that surround the city, as well as a waterpark for family-friendly fun. With its rich history and lively downtown area, Pittsfield is an ideal spot for those seeking both action and relaxation.
  • Williamstown: Situated 14 miles from Lanesborough, Williamstown is renowned for its stunning landscapes and outdoor adventures. This quaint city is home to Williams College, adding a touch of historic charm to the area. Visitors can enjoy skiing at the local ski resorts, while the nearby mountains and lakes provide perfect settings for hiking, fishing, and other outdoor activities. The combination of academic culture and natural beauty makes Williamstown a delightful destination for tourists looking to explore the Berkshires.

Best time to go to Lanesborough

If you're planning a trip to Lanesborough, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in June to July and September, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January19.9°F (-6.7°C)Light RainMostly CloudySlightly LowAverage
February22.1°F (-5.5°C)Light RainMostly CloudyAverageAverage
March29.7°F (-1.3°C)Light RainMostly CloudyAverageSlightly Low
April41.4°F (5.2°C)Light RainMostly CloudyAverageSlightly Low
May53.8°F (12.1°C)Light RainMostly SunnyAverageAverage
June61.5°F (16.4°C)Light RainMostly SunnySlightly HighAverage
July67.6°F (19.8°C)Light RainMostly SunnySlightly HighSlightly High
August65.7°F (18.7°C)Light RainMostly SunnyAverageSlightly High
September58.6°F (14.8°C)Light RainMostly SunnySlightly HighAverage
October47.7°F (8.7°C)Light RainMostly CloudyAverageSlightly Low
November35.4°F (1.9°C)Light RainMostly SunnySlightly LowAverage
December27.0°F (-2.8°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Vrbo is a breeze

Are you hoping to save on your next adventure? Being flexible with your travel dates can really help, as prices often vary. Additionally, opting for an extended stay typically allows you to enjoy significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you make the most of your travel experience with ease and confidence.

Save more with One Key

When you reserve a qualifying Vrbo for your group getaway, you’ll receive OneKeyCash on the total booking amount. Being the organizer has its perks. Become a member of our One Key rewards program to unlock exclusive savings and accumulate OneKeyCash on eligible stays. Sign up today and begin your journey to earning rewards.

Vrbo Trips: Planning as easy as it gets

Vrbo's new Trip Board feature offers you a dedicated space to plan your trips, pick up from where you last stopped, or keep track of your travel arrangements. You can easily find the properties you've saved or booked under Potential, Upcoming, or Current Trips. To explore the Trip Boards, visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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)
  • The Bookstore (11.4 mi / 18.3 km)
  • Wyndhurst Golf & Club (12.2 mi / 19.6 km)
  • Bas Ridge Golf Course (7.6 mi / 12.2 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 Reserve (9.8 mi / 15.8 km)
  • Wood's Pond (11.4 mi / 18.4 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, Massachusetts, United States of America when booking a vacation rental?
When considering a vacation rental in Lanesborough, Massachusetts, the area near the Berkshire Mountains offers a fantastic experience. This region is renowned for its stunning natural beauty and outdoor activities. Staying here puts you in close proximity to popular attractions like the picturesque Mount Greylock State Reservation, which boasts breathtaking views and numerous hiking trails. Additionally, you can explore the charming local art scene, with various galleries and cultural events that showcase the rich heritage of the Berkshires.

Another appealing option is the area around Pontoosuc Lake, where you can enjoy water activities like kayaking and fishing. This neighborhood offers serene surroundings and easy access to parks and walking trails.
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 traveling 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. To get the best value, book early and take advantage of Vrbo's free rewards program.
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 the best ski resort rentals near Lanesborough, Massachusetts, travelers should focus on the nearby town of Adams and the scenic area surrounding Jiminy Peak Mountain Resort, which is just a short drive away. Many vacation rentals in this region include cozy cabins and chalets that cater to skiing enthusiasts. These properties often come equipped with amenities such as fully stocked kitchens, fireplaces for warming up after a day on the slopes, and outdoor decks offering beautiful views of the snow-covered landscape.

In Adams, visitors can find charming homes that often feature spacious living areas, great for relaxing with family or friends after a long day of skiing. Many rentals are also pet-friendly, allowing furry companions to join in on the fun. The town provides convenient access to local dining options and shops, making it easy to stock up on supplies or enjoy a meal out.

Additionally, the surrounding Berkshires region offers a variety of outdoor activities beyond skiing, such as hiking and snowshoeing in the winter months. Rentals in this area provide a blend of comfort and rustic charm, often with amenities like game rooms or hot tubs, ideal for unwinding after an adventurous day.
What is the most popular type of vacation rental accomodation in Lanesborough?
In Lanesborough, vacation houses are the most popular rental option, with about 10 available throughout the area. Many of these properties are situated in peaceful, scenic locations that allow guests to enjoy the natural beauty of the Berkshires. Most vacation houses offer amenities such as multiple bedrooms, fully equipped kitchens, and outdoor spaces like decks or gardens, superb for relaxing after a day of exploring.

Additionally, there are several cottages, apartments, and condos available, providing a variety of choices for different group sizes and preferences. Cottages often feature charming interiors and cozy atmospheres, while apartments and condos can offer convenient locations for accessing nearby attractions.
Are there any family house rentals in Lanesborough?
In Lanesborough, Massachusetts, family-friendly house rentals are plentiful, with around 14 options available for those traveling with kids. This charming town is situated near the scenic Berkshire Mountains, offering plenty of outdoor activities. Many of the homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces superb for children's play. Visitors can also expect amenities such as Wi-Fi, air conditioning, and sometimes even game rooms to keep everyone entertained.

The area is close to various attractions, including the beautiful October Mountain State Forest, where families can enjoy hiking and picnicking, as well as the nearby Bousquet Mountain for seasonal activities.
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, making it an attractive option for travelers seeking relaxation. This charming town, located in the scenic Berkshires, offers a variety of rental properties that cater to families and groups. Many of these homes come equipped with private pools, inviting hot tubs, and outdoor spaces for gatherings, great for enjoying the beautiful surroundings.

Travelers can expect amenities such as fully equipped kitchens for meal preparation, spacious living areas, and comfortable bedrooms. Additionally, some properties may offer access to local attractions, including nearby lakes and hiking trails, allowing guests to fully immerse themselves in the natural beauty of the area.
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. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Lanesborough?
In Lanesborough, there are several pet-friendly house rentals available, making it a great destination for travelers with furry companions. Many of these vacation homes are situated in serene, wooded areas, offering a peaceful retreat while still providing easy access to outdoor activities. Expect amenities such as spacious backyards, fully equipped kitchens, and cozy living spaces that are superb for families or groups.

The town is close to the scenic Mount Greylock State Reservation, which features extensive hiking trails and breathtaking views, ideal for pet owners looking to explore the natural beauty of the region. Additionally, some rentals may offer features like fireplaces and outdoor seating areas, enhancing the overall experience for guests and their pets.
Are there any remote work vacation rentals in Lanesborough?
In Lanesborough, Massachusetts, there are several remote work vacation rentals available, with around 14 options to choose from. Many of these properties cater to the needs of remote workers, offering amenities such as dedicated workspaces with desks and chairs, as well as reliable Wi-Fi to ensure productivity during your stay.

The area is surrounded by the natural beauty of the Berkshires, providing a tranquil environment that can enhance your working experience. Travelers can expect comfortable living spaces with cozy interiors, and many rentals feature fully equipped kitchens, allowing for convenient meal preparation.

Lanesborough is also close to local attractions like the popular Berkshire Museum and the scenic Mount Greylock, great for unwinding after a day of work. 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 travelers 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 rental amenities include fully equipped kitchens, allowing travelers to prepare their own meals during their stay. Many properties also feature decks or patios, providing outdoor spaces for relaxation and enjoying the fresh air. Onsite parking is commonly available, making it convenient for guests with vehicles. Additionally, amenities such as blenders and coffee or tea makers are often included, enhancing the comfort and convenience of the vacation rentals.
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 peak season from June to August, with July being the most popular month. This vibrant period attracts travelers looking to embrace the warm weather and partake in a variety of outdoor activities. With temperatures typically ranging from the mid-70s to low 80s Fahrenheit, it's superb for enjoying hikes, exploring the picturesque landscapes, or even attending local summer events.

During this time, visitors can experience firsthand the lush beauty of the Berkshires, where opportunities for hiking, biking, and enjoying the scenic views abound. Lanesborough is not only rich in natural beauty but also offers cultural experiences, including art galleries and historical sites, all easily accessible for a fulfilling vacation.

For those seeking a more budget-friendly option, consider visiting in December. This quieter month offers a chance to experience the area's charm during the winter season, which can include holiday festivities and a cozy atmosphere superb for relaxation. While temperatures may dip into the 20s and 30s Fahrenheit, the serene winter landscape presents a unique beauty and a chance to enjoy local winter sports.
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.
What are the top attractions in Lanesborough, Massachusetts, United States of America?
In Lanesborough, Massachusetts, visitors can enjoy a variety of attractions that showcase the area's natural beauty and outdoor activities. One of the main highlights is the picturesque Lake Pontoosuc, where guests can partake in swimming, kayaking, and fishing. The surrounding scenic views make it a popular spot for picnicking and relaxation.

The nearby Mount Greylock State Reservation offers stunning hiking trails and panoramic views from the summit, which is the highest point in Massachusetts. This area is ideal for those looking to immerse themselves in nature and enjoy activities like hiking and birdwatching.

Lanesborough is also close to several cultural attractions, including the Berkshire Museum in nearby Pittsfield, which features art, history, and science exhibits.
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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing 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 favorites, and build the perfect itinerary together.

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