Lanesborough holiday lettings

We found 348 holiday rentals — enter your dates for availability

Discover a selection of 10 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:1 May - 8 May

Image gallery for Luxury Berkshires Retreat in Lenox - Main House & Studio

View of the main house on the left and guest house on the right
10 out of 10, Exceptional, (54 reviews)
Exceptional
(54 reviews)

Luxury Berkshires Retreat in Lenox - Main House & Studio

Lenox

6% off
Price is £7,638
for 7 nights, 1 home
£1,091 per night
includes taxes & fees
Luxury Berkshires Retreat in Lenox - Main House & Studio

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Why visit Lanesborough

  • Outdoor pursuits: Lanesborough is perfect for skiing and a variety of outdoor sports, catering to adventure seekers.
  • Charming neighbourhoods: Explore picturesque areas with delightful architecture and romantic scenery, ideal for leisurely strolls.
  • Family-friendly atmosphere: The area provides a welcoming environment for families, groups, and solo travellers.
  • Historic attractions: Discover local history through historic houses and nature reserves that showcase the region's charm.
  • Varied accommodation: Enjoy a range of lodging options, from luxurious hotels to cosy cottages, ensuring a memorable stay.

Popular types of accommodation in Lanesborough

Vrbo offers a delightful selection of vacation rentals in Lanesborough, catering to every traveler's needs. Whether you're seeking a luxurious room in a star-rated hotel, a charming cottage, or an exclusive private home, you'll find the perfect fit. For those planning to explore Maidenhead or enjoy spacious bedroom houses, our platform provides a variety of options to ensure a memorable stay. Discover the ideal accommodation for your next getaway today!

  • Houses: The top choice for visitors in Lanesborough, these spacious homes offer comfort and privacy, perfect for families or groups.
  • Condos: A popular option for those seeking modern amenities and convenience, these self-contained units provide a great base for exploring.
  • Cottages: Charming and often tucked away in nature, cottages offer a quaint retreat with a homely feel.
  • Cabins: Ideal for a rustic getaway, cabins provide a cozy atmosphere surrounded by beautiful landscapes.
  • Apartments: These versatile living spaces are perfect for couples or solo travellers looking for a convenient stay.**

Top attractions in and around Lanesborough

Lanesborough, Massachusetts, is an ideal destination for skiing, adventure, and sports holidays. Visitors can explore a variety of attractions including nature reserves, mountains, and historic houses. The area offers a wealth of opportunities for outdoor enthusiasts and those seeking cultural and adventurous experiences, making it a perfect spot for families, groups, or solo travellers looking to immerse themselves in the local charm.

  • Mount Greylock State Reservation Visitor Center: This visitor centre offers a gateway to adventure, surrounded by stunning natural beauty. Ideal for families, it provides information on local trails and activities, allowing you to embrace the great outdoors.
  • Mount Greylock: Located 5.6km from Lanesborough, this majestic mountain is perfect for hiking enthusiasts, offering breathtaking scenery and diverse wildlife. The views from the summit are simply unforgettable.
  • Williams College: Situated 8.1km away, this historic institution boasts beautiful architecture and rich cultural offerings, including art galleries and performances, making it a delightful stop for culture lovers.

Things to do recommended for couples

For a delightful couples' getaway in Lanesborough, indulge in skiing at Jiminy Peak Mountain Resort or Bousquet Ski Area, both offering exhilarating sports vibes. Alternatively, enjoy a romantic wine tasting at Furnace Brook Winery, where you can savour fine wines amidst enchanting surroundings.

Things to do recommended for families

Families can explore the serene Kennedy Park, located 6.2km away, and enjoy the Alpine Super Slide, a thrilling ride just 2.5km from Lanesborough. Additionally, Shatford Memorial Park offers a peaceful retreat, situated 5.0km from the town, perfect for relaxation and play.

Things to do recommended for groups

Enjoy a captivating performance at the Barrington Stage Company, just 3.1km from Lanesborough. For a bit of sport, head to the nearby Skyline Country Club for a round of golf. Don’t miss Zema's Nursery, located 5.0km away, for a unique shopping experience.

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

If you're travelling with a group, family, pets, or planning for extended stays, be sure to prioritise your filters accordingly. Here are some helpful booking tips for using Vrbo.

  • Traveling to Lanesborough with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Lanesborough with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, along with suitable facilities, like a private swimming pool. Additionally, considering your location in relation to family-friendly attractions is a wise approach.
  • Taking your pets with you to Lanesborough: For many, a family holiday wouldn’t be the same without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding 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 holiday rentals offering discounts for month-long stays, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. You might also want to consider including amenities such as a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Lanesborough

Lanesborough, Massachusetts, offers a delightful blend of adventure and tranquillity, making it ideal for families, couples, and budget-conscious travellers alike. Explore the stunning lakeside village, where you can indulge in skiing and outdoor sports. Nearby, discover charming neighbourhoods that offer romantic scenery and excellent architecture, perfect for a leisurely stroll. With its family-friendly atmosphere and coveted locations, Lanesborough promises a memorable getaway filled with diverse experiences.

  • Lenox: Lenox is a charming town located 6.8km from Lanesborough, renowned for its romantic and family-oriented atmosphere. Visitors flock to Lenox for a delightful blend of entertainment options, including music concerts and theatrical performances. The town is nestled amidst picturesque mountains and lakes, making it an ideal spot for outdoor enthusiasts. Don't miss the opportunity to explore the local events at the conference venue or to take in the stunning natural surroundings, which provide a perfect backdrop for a leisurely escape.
  • Pittsfield: Just 3.1km from Lanesborough lies Pittsfield, a vibrant city that promises adventure and sports for thrill-seekers. Known for its excellent skiing facilities, Pittsfield is a haven for winter sports enthusiasts, boasting ski fields and resorts that cater to all skill levels. The city is also home to beautiful lakes and a waterpark, providing plenty of options for family fun during warmer months. With its lively atmosphere and abundant recreational activities, Pittsfield is a great destination for those looking to engage in an action-packed getaway.
  • Williamstown: Situated 8.7km from Lanesborough, Williamstown is a delightful city that offers a mix of skiing and cultural exploration. Famous for its historic college, this town is steeped in academic charm and features stunning mountain and lake scenery. Williamstown is perfect for adventure lovers, with access to ski resorts and picturesque trails for hiking. Whether you’re interested in sports or soaking up the local history, Williamstown provides a unique experience that combines the thrill of outdoor activities with the richness of cultural heritage.

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 simple

Looking to make the most of your next holiday? Consider being flexible with your travel dates, as this can lead to significant savings. Moreover, opting for a longer stay frequently results in even better deals. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of holiday rental. We're here to help you find the perfect escape!

Vrbo Trips: Planning as easy as it gets

Vrbo's clever Trip Board offers you a dedicated space to plan new getaways, pick up where you last stopped, or review and arrange your travel plans. You can now easily locate properties you’ve saved or booked in the sections for Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/en-gb/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. 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)
  • 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)
  • Pineridge Cross Country Ski Center (17.1 mi / 27.5 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:

  • 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)

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, the area around the charming Main Street is a fantastic choice. This neighbourhood not only offers a quaint, small-town atmosphere but also places you near some delightful attractions. A short stroll will take you to the picturesque Berkshire Scenic Railway Museum, where you can immerse yourself in the region's rich railway history. Additionally, the stunning Lake Pontoosuc provides a serene setting for outdoor activities such as fishing, kayaking, or simply enjoying a peaceful picnic by the water.
How much does it cost to rent a holiday home in Lanesborough?
Prices for holiday 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 holiday house rentals?
You can find great discounts on house rentals in Lanesborough on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best Lanesborough ski resort rentals?
For ski resort rentals near Lanesborough, Massachusetts, the nearby Jiminy Peak Mountain Resort is the place to focus on. Located just a short drive from Lanesborough, this resort offers a variety of accommodations in the surrounding area, particularly in the quaint town of Hancock. Properties here often include spacious lodges and charming cabins that cater to families and groups. Many of these rentals feature amenities such as full kitchens, access to hot tubs, and fireplaces, providing a cozy atmosphere after a day on the slopes.

In addition to Hancock, the town of Lanesborough itself has various options, including holiday homes and condos that are conveniently situated for accessing nearby skiing and snowboarding activities. These properties typically come equipped with modern comforts, including Wi-Fi and laundry facilities, making them ideal for longer stays.
What is the most popular type of holiday rental accomodation in Lanesborough?
In Lanesborough, holiday houses are the most popular type of rental, with about 11 available in the area. These houses typically offer spacious living arrangements, making them ideal for families or groups looking to enjoy a cozy feel. Many feature multiple bedrooms, fully equipped kitchens, and outdoor spaces where guests can relax and enjoy the natural surroundings. In addition to holiday houses, there are several apartments, cottages, and condos available, providing a range of choices to suit different preferences.
Are there any family house rentals in Lanesborough?
In Lanesborough, Massachusetts, there are numerous family-friendly holiday rentals available, with around 16 options to choose from. This charming town offers a delightful mix of outdoor activities and cultural experiences, making it an excellent choice for families. Many of the properties feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play safely.
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 picturesque Berkshires, offers a tranquil retreat with opportunities for outdoor activities and relaxation. Many of the properties come equipped with amenities such as private pools, hot tubs, spacious outdoor areas, and fully stocked kitchens, making them ideal for families or groups looking to enjoy a comfortable stay.
Can I find long-stay holiday rentals in Lanesborough?
A long-stay holiday rental in Lanesborough is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Lanesborough?
In Lanesborough, there are several pet-friendly house rentals available, offering a welcoming environment for travellers with pets. Many of these properties come equipped with essential amenities such as fully stocked kitchens, spacious living areas, and outdoor spaces where pets can enjoy the fresh air.
Are there any remote work holiday rentals in Lanesborough?
In Lanesborough, Massachusetts, there are a variety of remote work holiday rentals available, with around 16 options to choose from. This charming town, located in the Berkshires, is known for its natural beauty and tranquil environment, making it an ideal setting for remote work. Many of the properties feature dedicated office spaces or desks, fast Wi-Fi, and comfortable workstations, including desk chairs and computer monitors, ensuring a productive atmosphere for those working from home. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Lanesborough holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Lanesborough with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Lanesborough?
In Lanesborough, popular holiday rental amenities typically include fully equipped kitchens, which are essential for preparing meals during your stay. Most properties come with refrigerators, stovetops, cookware, dishware, and utensils, making it convenient for guests to enjoy home-cooked meals. Additionally, many rentals offer microwaves, providing an extra level of convenience for quick snacks or reheating leftovers.
When is the best time to visit Lanesborough for a holiday rental?
The best time to book a holiday rental in Lanesborough is during the summer months, particularly in July, when the area truly comes alive. This peak season, spanning from June to August, attracts visitors eager to bask in the warm weather and engage in a myriad of outdoor activities, including hiking and exploring the scenic beauty of the Berkshires.

In July, temperatures typically hover in the mid to high 20s Celsius, providing a comfortable climate for those keen on sightseeing or enjoying lakeside picnics. The lush landscapes and vibrant greenery create a stunning backdrop, great for leisurely walks or cycling along picturesque trails.

For those seeking a more budget-friendly option, consider planning your visit in December. While this month is less busy, it offers a unique charm, with opportunities for winter sports and a peaceful atmosphere great for a retreat.
How early should I book a Lanesborough holiday rental?
Book your Lanesborough holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Lanesborough home rental booking on Vrbo?
To find Lanesborough holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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