Lanesborough vacation rentals

We found 342 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:Apr 3 - Apr 10

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

Interior
10 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)

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

Richmond

18% off
Price is $336
$2,354 for 7 nights
All fees included
New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.

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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)
  • 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)
  • Wyndhurst Golf & Club (12.2 mi / 19.6 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)
  • Lenox Mountain Reserve (9.8 mi / 15.8 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 best area to stay is near the scenic shores of Pontoosuc Lake. This neighborhood offers a peaceful retreat surrounded by nature, great for those looking to unwind while still being close to local attractions. The area typically has a variety of vacation rentals available, ranging from cozy cabins to charming cottages, allowing visitors to choose accommodations that best suit their preferences.

Pontoosuc Lake is not only a beautiful spot for relaxation but also provides opportunities for outdoor activities like kayaking, fishing, and hiking along the nearby trails. Additionally, being close to the town center allows easy access to local dining options and shops. Another highlight of staying in this area is the proximity to the Mount Greylock State Reservation, where you can enjoy breathtaking views, hiking trails, and a chance to explore the natural beauty of the Berkshires.
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 ski resort rentals near Lanesborough, Massachusetts, travelers will find excellent options in the nearby town of Pittsfield and the charming community of Williamstown, both of which provide convenient access to the slopes of Jiminy Peak, located just a short drive away. In Pittsfield, visitors can discover modern condominiums and cozy vacation homes that often come equipped with amenities such as full kitchens, comfortable living areas, and sometimes even fireplaces, creating a welcoming environment after a day on the mountain.

In Williamstown, known for its picturesque New England charm, there are also various rental options, including quaint cottages and larger homes suitable for families or groups. Many of these properties feature beautiful views of the surrounding mountains, outdoor space for relaxation, and easy access to local dining and shopping. This area is particularly appealing for those who appreciate both skiing and the cultural offerings of Williams College and the Clark Art Institute.

Additionally, travelers should consider accommodations that provide proximity to nearby outdoor activities, including hiking and snowshoeing trails. Rentals in both Pittsfield and Williamstown often include amenities such as ski storage, access to hot tubs or communal pools, and facilities for grilling, making them ideal for those looking to enjoy a winter getaway filled with both adventure and comfort.
What is the most popular type of vacation rental accomodation in Lanesborough?
In Lanesborough, vacation houses are the most common type of rental, with about 11 available in the area. These properties typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups looking for a comfortable home base. Additionally, several apartments and cottages can be found, offering a more compact yet cozy alternative. These options often include amenities such as outdoor seating areas and access to scenic views, great for relaxing after exploring nearby attractions like the Berkshire Mountains and the serene waters of Pontoosuc Lake.
Are there any family house rentals in Lanesborough?
In Lanesborough, Massachusetts, there are several family-friendly house rentals available, offering a comfortable base for exploring the area. Many properties feature spacious living areas, full kitchens for preparing meals, and some even include outdoor spaces great for kids to play. Visitors can expect amenities such as Wi-Fi and laundry facilities, which add to the convenience of their stay.

This charming town is close to attractions like the picturesque Berkshire Mountains, where families can enjoy hiking and outdoor activities. Additionally, the nearby town of Williamstown, home to the renowned Williams College and the Clark Art Institute, provides cultural experiences and beautiful landscapes.
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. This picturesque area, located near the scenic Berkshire Mountains, offers a tranquil setting for travelers looking to unwind. Many of these rentals provide amenities such as private pools, hot tubs, outdoor patios, and well-equipped kitchens, making them ideal for both relaxation and family gatherings.

Travelers can also enjoy nearby attractions, including hiking trails and local parks, enhancing their outdoor experience.
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, Massachusetts, there are several pet-friendly house rentals available, providing a welcoming environment for travelers with furry companions. Many of these properties feature amenities such as spacious backyards, allowing pets to roam freely, and fully equipped kitchens for convenient meal preparation. Travelers can expect cozy living areas, often with fireplaces, and comfortable bedrooms that make for a relaxing stay.

The area is known for its scenic beauty, with access to nearby attractions like the beautiful Berkshire Mountains, which offer plenty of outdoor activities such as hiking and nature walks. Additionally, the nearby Pittsfield State Forest is a fantastic spot for exploring with pets, with its trails and picturesque landscapes.
Are there any remote work vacation rentals in Lanesborough?
In Lanesborough, Massachusetts, there are several remote work-friendly vacation rentals available, with around 16 options to choose from. This picturesque town, located in the Berkshires, provides a tranquil setting ideal for combining work and leisure. Travelers can expect rentals equipped with essential amenities for remote work, including dedicated office spaces, desks, and comfortable chairs, along with reliable Wi-Fi to ensure smooth connectivity.

Many properties also feature inviting living areas, fully equipped kitchens for meal preparation, and outdoor spaces to enjoy the serene natural surroundings during breaks. Lanesborough's proximity to attractions such as the Berkshire Museum and hiking trails in the nearby Mount Greylock State Reservation adds to its appeal, allowing for a balanced lifestyle while working remotely. 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 vacation rental amenities include kitchens, which allow guests to prepare their own meals, and WiFi for staying connected. Many rentals also feature coffee and tea makers, making it easy to enjoy a warm beverage at any time. Outdoor spaces are common as well, with patios providing a superb spot for relaxation and enjoying the fresh air. Additionally, some properties may offer kitchen islands, giving extra space for meal prep and gathering.
When is the best time to visit Lanesborough for a vacation rental?
The best time to book a vacation rental in Lanesborough is during the peak season, which spans from June to August. This summer period is particularly popular among travelers seeking outdoor adventures, as it offers a delightful climate and a variety of activities. With temperatures typically ranging from the mid-60s to the mid-80s Fahrenheit, the warm weather beckons visitors to explore the beautiful landscapes, including the stunning Berkshire Mountains and nearby hiking trails.

July stands out as the most vibrant month in Lanesborough, drawing travelers. The region comes alive with cultural events, local festivals, and outdoor concerts, providing ample opportunities for entertainment and socializing. Whether you're kayaking on the serene lakes or enjoying a casual stroll through the charming town, the summer atmosphere is unmistakably inviting.

For those looking to travel on a budget, visiting in December can be an appealing option. While this month is considered the low season, it presents a unique opportunity to experience the tranquil beauty of Lanesborough covered in snow. You can enjoy winter activities such as cross-country skiing or cozying up by the fire in your vacation rental after a day of exploring.

In summary, your choice of when to visit Lanesborough should align with your personal preferences—whether you thrive in the lively summer scene or prefer the peacefulness of winter.
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?
In Lanesborough, Massachusetts, visitors can enjoy a variety of attractions in the surrounding areas. The town is home to the scenic Berkshire Mountains, which offer numerous outdoor activities such as hiking, skiing, and leaf-peeping during the fall. Nearby, the iconic Mount Greylock State Reservation provides stunning vistas and trails for nature lovers.

The town is also close to the cultural hub of the Berkshires, where travelers can explore attractions like the Norman Rockwell Museum in Stockbridge and Tanglewood, the summer home of the Boston Symphony Orchestra, located in Lenox.
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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