Lanesborough vacation rentals

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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:May 22 - May 29

Image gallery for Ski at Historic Stone Church in The Berkshires

Interior
10 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)

Ski at Historic Stone Church in The Berkshires

Lanesborough

9% off
Price is $353
$2,470 for 7 nights
All fees included
Ski at Historic Stone Church in The Berkshires

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Find out more about Lanesborough

Why visit Lanesborough

  • Outdoor Adventures: Lanesborough is a paradise for ski and adventure enthusiasts, with stunning mountains ideal for skiing and other outdoor activities.
  • Nature Preserves: Explore the area's natural beauty through various nature preserves, perfect for hiking and wildlife observation.
  • Charming Accommodations: Choose from a range of vacation rentals, including cozy cottages and modern condos, to enhance your stay.
  • Historic Sites: Discover historic houses that reflect the rich cultural heritage of Lanesborough.
  • Family-Friendly Activities: With diverse attractions, Lanesborough offers fun and adventure for families of all sizes.

Popular types of accommodation in Lanesborough

Lanesborough offers a variety of vacation rentals to suit every traveler's needs. Whether you're looking for houses, cozy cottages, or modern condos, you'll find the perfect spot to unwind. For those seeking outdoor adventures, Lanesborough campgrounds provide a great way to immerse yourself in nature. Explore our selection of house rentals and vacation homes to create unforgettable memories in this charming town.

  • Houses: The top choice for travelers in Lanesborough, these homes offer spacious and comfortable accommodations for families or groups.
  • Condos: A popular option for vacationers seeking modern amenities and a convenient location, condos provide a great blend of comfort and style.
  • Cottages: Charming and cozy, cottages in Lanesborough offer a quaint retreat for those looking to enjoy the area's natural beauty.
  • Cabins: Ideal for a rustic escape, cabins provide a peaceful setting among nature, perfect for relaxation.
  • Apartments: A versatile choice, apartments are great for solo travelers or couples wanting easy access to local attractions.**

Top attractions in and around Lanesborough

Lanesborough, Massachusetts, is an ideal destination for ski and adventure enthusiasts, offering a mix of outdoor activities and cultural experiences. Explore local points of interest such as nature preserves, scenic mountains, and historic houses. Whether you're looking for vacation ideas, weekend getaways, or the best vacation rentals, Lanesborough has something for everyone seeking adventure and relaxation in a beautiful setting.

  • Mount Greylock State Reservation Visitor Center: A hub for adventure seekers and families, this visitor center offers engaging exhibits and access to beautiful trails, making it the perfect starting point for exploring the outdoors.
  • Mount Greylock: Located 9 miles away, this majestic mountain boasts breathtaking scenery and a variety of trails for hiking, providing an exhilarating outdoor experience amidst nature's beauty.
  • Williams College: Situated 13 miles from Lanesborough, this historic institution features stunning architecture and a vibrant cultural scene, including art galleries and performances, enriching your visit with an academic charm.

Things to do recommended for couples

For a romantic getaway in Lanesborough, explore the slopes at Jiminy Peak Mountain Resort or Bousquet Ski Area for thrilling winter sports. Then, unwind at Furnace Brook Winery at Hilltop Orchards, savoring exquisite wines and enjoying a cozy atmosphere perfect for couples.

Things to do recommended for families

Your family vacation in Lanesborough, Massachusetts, can include exciting rides at the Alpine Super Slide, relaxation at Kennedy Park, and outdoor fun at Shatford Memorial Park. Each location offers unique experiences perfect for creating lasting memories together.

Things to do recommended for groups

Groups visiting Lanesborough can enjoy a captivating performance at Barrington Stage Company, play a round of golf at Skyline Country Club, and explore the unique offerings at Zema's Nursery for a delightful local experience.

*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

If you're traveling with a group, family, or pets, or planning an extended stay, be sure to set your filters according to your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Lanesborough with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor area for group gatherings. Fortunately, you can easily filter for these options and much more on Vrbo.
  • Traveling to Lanesborough with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, along with amenities suited for their age, like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Lanesborough: For many, a family vacation isn't truly fulfilling without their furry companion along for the adventure. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly accommodations offer amenities like food bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Lanesborough: If you're in search of vacation rentals offering special rates 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 rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Lanesborough

Lanesborough, Massachusetts, is a hidden gem perfect for adventure seekers and families alike. With its stunning mountainside getaways, visitors can enjoy skiing and outdoor activities while soaking in the area's natural beauty. Nearby cities and neighborhoods offer a blend of romantic scenery and budget-friendly options, making it an ideal destination for everyone. Experience the charm of Lanesborough and discover the best places to explore in this captivating region.

  • Lenox: Located 11 miles from Lanesborough, Lenox is a charming town that offers a blend of entertainment and romance. It's a prime destination for families seeking fun and relaxation. Visitors can enjoy music concerts and theater performances, or hit the slopes for skiing in the winter months. The stunning natural surroundings include picturesque lakes and mountains, perfect for outdoor enthusiasts. Don't miss the event conference venues that often host exciting cultural events throughout the year.
  • Pittsfield: Just 5 miles away from Lanesborough, Pittsfield is an adventure hub, particularly for skiing and sports enthusiasts. The city boasts access to several ski resorts and fields, providing thrilling winter sports experiences. In addition to skiing, visitors can enjoy the nearby lakes and a waterpark for summer fun. With its vibrant community and array of outdoor activities, Pittsfield is a must-visit for anyone looking to embrace adventure during their stay.
  • Williamstown: Situated 14 miles from Lanesborough, Williamstown is known for its rich history and scenic beauty. This city is another great spot for skiing and outdoor sports, with excellent access to ski fields and resorts. Visitors can explore the historic college university, which adds a unique cultural charm to the area. The surrounding mountains and lakes provide ample opportunities for hiking, boating, and enjoying the great outdoors, making Williamstown a perfect addition to your travel itinerary.

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 upcoming adventure? Being open to adjusting your travel dates can be a great way to take advantage of varying prices. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the best options for your needs.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your entire booking. Being the planner definitely has its perks. When you join our travel rewards program, One Key, you'll gain access to exclusive discounts and earn OneKeyCash on qualifying reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers an easy-to-use platform for planning your travels. You can create new trips, continue from where you left off, or manage your existing plans all in one place. Here, you'll see the properties you've saved or reserved neatly organized into categories like Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply 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)
  • Kennedy Park (9.8 mi / 15.8 km)
  • The Bookstore (11.4 mi / 18.3 km)
  • Furnace Brook Winery at Hilltop Orchards (11.6 mi / 18.7 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)
  • Kennedy Park (9.8 mi / 15.8 km)
  • Queechy Lake (12.2 mi / 19.6 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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