Photo by Caitlin Reese

Lanesborough holiday lettings

We found 369 holiday rentals — enter your dates for availability

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

Holiday rentals with weekly discounts - Lanesborough

Showing deals for:3 Oct - 10 Oct
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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.

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!

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

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.

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)
  • Waubeeka Golf Links (9.7 mi / 15.6 km)
  • Kennedy Park (9.8 mi / 15.8 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 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)
  • Wahconah Falls State Park (6.2 mi / 9.9 km)
  • Brodie Mountain (8.2 mi / 13.2 km)
  • Mount Greylock (8.9 mi / 14.3 km)
  • Mount Greylock State Reservation (8.9 mi / 14.4 km)
  • Pleasant Valley Wilderness Sanctuary (9.3 mi / 15 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 most popular type of holiday rental accommodation in Lanesborough?
Based on our research, houses are the most popular holiday property type in Lanesborough. But of course, everyone's idea of an epic stay is bound to be different. Vrbo has holiday rentals with every shape, size and budget in mind, and we'll help you locate your ideal match.
How much does it cost to rent a holiday rental in Lanesborough?
The average price for a holiday rental in Lanesborough can vary based on factors including season, length of stay and property type. Whether you're thinking about a sprawling villa with space for extended family or a quaint cabin that's perfect for two, just enter your travel dates to discover stays with great value.
How much does it cost to rent a beach house in Lanesborough?
The average price for a holiday home close to the beach in Lanesborough depends on when you'll be there and the style and size of property you're looking for. Find prices quickly and easily on Vrbo by entering your destination and preferred travel dates. Then use our filters to select the number of bedrooms and amenities that you prefer, like a pool, air conditioning and WiFi.
Are there pet-friendly holiday rentals in Lanesborough?
Yes. You can pick from 19 holiday rentals that cater to pets in Lanesborough. Some of our pet-friendly holiday rentals come with space outdoors for your fur baby to play around in, doggie beds, complimentary treats and proximity to parks or green space. Apply the "Pets allowed" filter to find your pawfect digs on Vrbo.
Can I rent a house with a pool in Lanesborough?
Pack your swimwear and goggles, because there are three houses with a private pool in Lanesborough. Unwind at one of these popular holiday rentals and enjoy a pool day every day. Simply enter your travel dates into Vrbo, then check the "pool" filter to find the perfect place to make a splash!
What are popular rental amenities in Lanesborough?
A garden, ski-in/ski-out facilities and a lake view top the list of most popular rental amenities in Lanesborough. Whether you're heading away alone, with your spouse or a bunch of friends, Vrbo can help you find a holiday rental that fits your tastes with all the features you need.
Are there large group holiday rentals in Lanesborough?
With four properties that can sleep 10 or more guests in Lanesborough, you don't have to hold back on your invites. From extended family holidays to events like birthday parties and weddings, Vrbo can help you find a large group rental that fits the occasion.
Are there holiday rentals in Lanesborough that welcome kids?
With 18 family-friendly holiday rentals available in Lanesborough, now is an awesome time to introduce your children to the magic of travel. Just check our "Properties good for families" filter box to find stays packed with amenities ideal for holidaying families, such as extra bedrooms, swimming pools, hot tubs and bunk beds.
What are the top attractions for families in Lanesborough?
Keep the kids entertained at these top family-friendly attractions in Lanesborough:

  • Berkshire Museum
  • Arrowhead Museum
  • Mount Greylock

Are there one-bedroom holiday rentals in Lanesborough?
Lanesborough has five one-bedroom rentals on offer. Often located in popular areas because of their compact size, a one-bedroom holiday rental is great if you're getting away with your partner or a friend. And with comforts such as kitchens and more privacy than a standard hotel, you'll be able to kick back while discovering this fabulous destination.
Can I find two-bedroom holiday rentals in Lanesborough?
Take your pick of six two-bedroom properties in Lanesborough. Give the kids the second room or maybe fill it with a couple of your favourite people. There's a comfy spot for whoever's fortunate enough to be joining your adventure.
Are there holiday rentals with WiFi in Lanesborough?
Lanesborough has six holiday rentals with WiFi, so you can stay connected when you're away. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming movies with the family to checking emails, these Vrbo homes make it a cinch to go online.
How can I find holiday rentals with air conditioning in Lanesborough?
Lanesborough has 14 holiday rentals where you can relax in air-conditioned comfort. To find a stay on Vrbo that offers this perk, enter your travel dates and use the handy filters to select the "air conditioning" box.
How old do you have to be to rent a holiday rental in Lanesborough?
The minimum age permitted can differ across properties on Vrbo, so be sure to check the rules of the holiday home in Lanesborough you're considering. But in general, it's 16, 18 or 21.
How long can I rent a holiday rental in Lanesborough for?
It's down to the Lanesborough property. To view a list of options offering extended stays, just enter your travel dates and guest number into Vrbo. Look forward to having the place to yourself, along with comforts such as a fully-equipped kitchen and outdoor spaces where the kids can play. Keep your eyes open for long-term stays that offer discounted weekly or monthly prices.

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