Discover a selection of 218 vacation rentals in Lanesborough, MA that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $100 per night, and houses and condos are popular options for a stay in Lanesborough. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Lanesborough
Destination guide

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, HomeAway 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.

Things to do

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)
  • Furnace Brook Winery at Hilltop Orchards (11.6 mi / 18.7 km)
  • Cranwell Golf Club (12.2 mi / 19.6 km)
  • Kennedy Park (9.8 mi / 15.8 km)
  • Hotchkiss Mobile Studio (14.5 mi / 23.3 km)
Natural features

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)
  • Pittsfield State Forest (5.5 mi / 8.9 km)
  • Brodie Mountain (8.2 mi / 13.2 km)
  • Mount Greylock (8.9 mi / 14.3 km)
  • October Mountain State Forest (12.7 mi / 20.5 km)
  • The Mount (12.8 mi / 20.7 km)
How to get there

Transportation options to and around Lanesborough

The nearest airport is in Albany Intl. Airport (ALB), located 33.5 mi (53.9 km) from the city center. If you're unable to find a flight that fits your schedule, you might consider flying into Pittsfield, MA (PSF-Pittsfield Municipal), which is 7.1 mi (11.5 km) away.

What are the top vacation rentals in or near Lanesborough?

The heart wants what it wants, and right now it's craving a vacation. It's time to pack your bags and take off to one of these top vacation rentals in or near Lanesborough:

  • "Close To Skiing Beautiful +family Friendly" is a hit with guests. Around 30 miles from Lanesborough, it has 4 bedrooms and loads of useful amenities, including a games room and cookware, dishware and utensils.
  • Another top choice is "4br/3bath Lakefront/ski House In Berkshires. Fully Fitted Kitchen. Hi Speed Wifi", which is around 25 miles from Lanesborough. Featuring 4 bedrooms, a garden and internet services, it has everything you need to make your stay comfortable.

For even more great options, use the search bar at the top of the page to find the perfect Lanesborough vacation rental for you.

Can I find log cabins to rent in or near Lanesborough?

Sometimes, you just want to get away from the hurly-burly of daily life. That's where Vrbo can help. We've got an excellent selection of log cabin rentals in and around Lanesborough where you can unwind in nature. Try these on for size:

  • "Water Front Log Cabin Next To Tanglewood" is a fabulous mixture of outdoor fun and creature comforts. Take advantage of top amenities here including a kitchen island and high-speed internet services.
  • After a full day of being outdoors, unwind at "Log Cabin By Berkshire East". This cozy retreat comes with a host of features, including an oven and a balcony.

What are the top-rated vacation rentals for weekend getaways in or near Lanesborough?

Forget about those household chores — weekends were made for having fun. Head for one of these weekend getaways in and around Lanesborough and enjoy all the fantastic things to do close by:

  • Located 14 miles to the southeast of central Lanesborough, "Swiss Chalet Style Timber Frame Home In Berkshires With All Modern Conveniences" is popular among adventure lovers and nature fans. Get out and discover nearby attractions, including Talcott Greenhouse and Ashintully Gardens. If it's activities you're interested in, try horse riding or golf.
  • "Unique People And Pet - Welcoming Country Haven" is another great property to consider. Around 25 miles east of Lanesborough, use it as a base to try some mountain biking or horse riding. Hadley Farm Museum and Swift River also have to be on your itinerary while you're here.

Can I find studio apartments for rent in and around Lanesborough?

Enjoy a taste of the culture and lifestyle of Lanesborough from the privacy and comfort of a studio apartment. Whether you want to take a break on your own or live it up with buddies, you'll find the perfect studio apartment in or near Lanesborough:

  • Put your bags down and your feet up at "Unique People And Pet - Welcoming Country Haven". Amenities including a living room and a porch will help you feel right at home here.
  • Another tempting choice is "The Clearing - Quiet - Close To Nature". Take advantage of beach sun loungers, free WiFi and other handy amenities during your getaway.

When you're ready to walk out of your studio apartment and cross off the sights, there's plenty to keep you on the go around Lanesborough. Passionate about culture? Check out SoWa Artists Guild and DeCordova Sculpture Park and Museum.

Can I find short term rentals in or near Lanesborough?

Just because you only have a day or two free doesn't mean you have to spend it in a dull hotel room. Take off on vacation but still have the comforts of home at one of these short-term rentals in or around Lanesborough:

  • "Swiss Chalet Style Timber Frame Home In Berkshires With All Modern Conveniences" is close to the heart of Lanesborough, which means you'll have lots of things to do and see. Explore unique attractions like Walden Pond and Louisa May Alcott's Orchard House when you're not relaxing in your cozy pad.
  • "Unique People And Pet - Welcoming Country Haven" is another fabulous option. We recommend adding Old Manse and Concord Visitors Center to your travel itinerary when it's time to sightsee.

What are the best romantic weekend getaways in or near Lanesborough?

Whether spent in a rustic cabin or a luxury condo, a romantic weekend getaway is a perfect way to say "I love you." Whisk your honey off for a couple of days at one of these appealing escapes in or near Lanesborough:

  • Put on some relaxing music and kick back together at "4br/3bath Lakefront/ski House In Berkshires. Fully Fitted Kitchen. Hi Speed Wifi". Around 25 miles from Lanesborough, this property has everything you need for a romantic getaway, including outdoor furniture and a nearby marina.
  • Otherwise, spend a few magical days sipping wine and canoodling at "Elterwater - - Your Lakefront Oasis", around 30 miles from Lanesborough. Winery tours and beauty services will help set the mood for romance.

What are the best houses for rent with a pool in or near Lanesborough?

Nothing screams fun and frivolity like a pool does. Pump up your inflatable flamingo and browse these rental houses in or near Lanesborough that feature this vacation must-have:

  • Pack your swim gear and book a few days or more at "4br/3bath Lakefront/ski House In Berkshires. Fully Fitted Kitchen. Hi Speed Wifi". There are also lots of other appealing amenities here, including a balcony and beach sun loungers.
  • Spend leisurely vacation days splashing around or enjoying peaceful moments beside the water at "General Williams Estate House Lenox". This property is another favorite and features a fridge, a video library and more.

Unsure what to pack for your Lanesborough break? This impressive destination has a humid continental climate. During the summer months, expect average temperatures ranging from 55 ºF to 75 ºF. Browse our range of Lanesborough vacation rentals by using the search bar at the top of the page. Simply adjust the filters to get more great ideas about where to stay.

What are the best large family vacation rentals in or near Lanesborough?

Every family catch-up should be memorable. Whether you're organizing an action-packed escape with the kids or a reunion with the extended family, these large family vacation rentals in or near Lanesborough offer a home away from home with plenty of space for everyone:

  • Sleeping as many as 10 guests in 4 bedrooms, "4br/3bath Lakefront/ski House In Berkshires. Fully Fitted Kitchen. Hi Speed Wifi" is the ideal place to enjoy some family time. This retreat is 25 miles to the south of Lanesborough and has creature comforts such as free toiletries and a kitchen.
  • Another popular option is "The Playhouse: 7, 000 Square Feet Of Berkshires Modern Luxury And History". This property is 16 miles south of Lanesborough and comes with a garden, a microwave oven and more. With 6 bedrooms accommodating up to 20 people, there's no need to leave anyone off your invitation list.

If you're eager to visit some family-friendly attractions around the area, there's no shortage of choice. New England Aquarium, Newbury Street and CoCo Key Water Resort - Boston promise lots of fun for all ages.

Can I find family cabin rentals in or near Lanesborough?

Cozy up with your kiddos in a family cabin rental in or near Lanesborough and get set to build some lovely new memories together. Check out these options:

  • "Cabin - A - Frame In Sherwood Forest" - Located about 16 miles southeast of the center of Lanesborough, this family-friendly getaway comes with a DVD player and pet-friendly facilities.
  • "Quiet Comfortable Cabin 5 Min. Walk To Swimming And Boating" - This stay is also ideal for a family getaway and is around 20 miles southeast of Lanesborough. Offering outdoor furniture, a barbecue grill and more, it'll get everyone's tick of approval.

For more options, use the search bar at the top of the page and adjust the filters to find the Lanesborough vacation rental that's perfect for your needs.

What are the best large houses to rent with indoor pools in or near Lanesborough?

Take a dip anytime you please when you stay at one of our large rental houses with an indoor pool. Slip on your swimsuit and consider these retreats in or near Lanesborough that feature this head-turning perk:

  • Stay at "Private, Mountain Retreat With Indoor Pool And Fantastic Westward Mountain Views" and while away your days poolside. This popular option has 5 bedrooms that sleep up to 10 guests and a range of other great amenities. A fireplace and a sauna are among them.
  • Besides its fancy indoor pool, "Equipped Villa With Access To Pools" features an electric car charging station and a garden. It has 3 bedrooms that can cater for up to 8 people, so you can bring your entire crew along.

For more options, use the search bar at the top of the page and adjust the filters to find the Lanesborough vacation rental that's perfect for your needs.