Vacation rentals in Lanesborough

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Lanesborough

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Cottage in Lanesborough

4.93 out of 5 average rating, 220 reviews

Stone School Cottage

Romantic getaway or family vacation. Charming stone building served as a one-room schoolhouse from 1832 until 1950. Beautifully situated amidst horse farms on the scenic road to Mt Greylock, centrally located midway between Williamstown and Lenox. We host lots of writers and musicians who love the bright airy space, families that have fun in this big playhouse, and couples seeking a memorable and private retreat. PLEASE NOTE: this truly-unique building has an unusual layout, described below.

Apr 14 – 21

ﺩ.ﺇ622 per night
Guest favorite

Apartment in Lanesborough

5.0 out of 5 average rating, 21 reviews

Cozy Berkshire Waterfront Home

Welcome to our charming waterfront home on Pontoosuc Lake! The Berkshire Lakescape is perfect for a romantic getaway for a couple or two, or a solo adventure away. Soak in lake views from the deck or try to catch a stunning sunset from the water’s edge. Kayak straight from our backyard and return for marshmallows at the firepit. Explore Berkshires' culture and outdoor activities - Tanglewood, Mount Greylock, and more are just a short drive away. We can't wait to host you for a memorable stay.

Sep 14 – 21

ﺩ.ﺇ841 per night
Guest favorite

Condo in Hancock

4.83 out of 5 average rating, 131 reviews

Cozy Condo @ Jiminy Peak

Nestled in the majestic Berkshire mountains, this Cozy Condo is a home away from home! It features 2 bedrooms with closets & dresser space. The master bedroom connects to a full bathroom and has a TV for when it's time to unwind in the comfort of bed! The fully equipped kitchen/dining area opens into a spacious living room. It's the perfect place for evening gatherings with friends or a romantic night in front of the fireplace! Free access to 2 heated pools, hot tubs, sauna & fitness center.

Aug 1 – 8

ﺩ.ﺇ592 per night

Popular amenities for Lanesborough vacation rentals

Stay near Lanesborough's top sights

Jiminy Peak200 locals recommend
Mount Greylock State Reservation Visitor Center39 locals recommend
Olde Forge Restaurant39 locals recommend
Bob's Country Kitchen6 locals recommend
Ashuwillticook Rail Trail74 locals recommend
Whitney's Farm Market & Garden Center20 locals recommend

Other great vacation rentals in Lanesborough

Superhost

Cabin in Lanesborough

4.83 out of 5 average rating, 52 reviews

Cozy stream-side cabin

May 16 – 23

ﺩ.ﺇ507 per night
Guest favorite

Home in Lanesborough

4.93 out of 5 average rating, 15 reviews

The Pond House

Aug 23 – 30

ﺩ.ﺇ905 per night
Guest favorite

Apartment in Pittsfield

4.92 out of 5 average rating, 24 reviews

Comfortable Pittsfield Loft

Feb 1 – 8

ﺩ.ﺇ276 per night
Guest favorite

Home in Lanesborough

5.0 out of 5 average rating, 88 reviews

Tranquil mid-century modern Berkshires retreat

Apr 3 – 10

ﺩ.ﺇ1,350 per night
Guest favorite

Apartment in Pittsfield

5.0 out of 5 average rating, 41 reviews

Simply off North

Sep 23 – 30

ﺩ.ﺇ305 per night
Guest favorite

Cottage in Lanesborough

4.98 out of 5 average rating, 46 reviews

Amazing 2 bedroom lake front cottage, large patio

Sep 12 – 19

ﺩ.ﺇ1,525 per night
Guest favorite

Home in Lanesborough

4.98 out of 5 average rating, 54 reviews

Cozy Cottage in Berkshires: Minutes to Jiminy Peak

Aug 4 – 11

ﺩ.ﺇ846 per night
Guest favorite

Home in Lanesborough

4.95 out of 5 average rating, 88 reviews

Berkshire Bliss- 6BR/Minutes from Jiminy +38 acres

Sep 29 – Oct 6

ﺩ.ﺇ3,166 per night
Guest favorite

Home in Adams

4.91 out of 5 average rating, 64 reviews

Mountain View Hideaway

Feb 11 – 18

ﺩ.ﺇ436 per night
Guest favorite

Home in Lanesborough

5.0 out of 5 average rating, 31 reviews

Lake Views, Lrg Open Grand Room+Kitchen, Hot Tub

Jul 28 – Aug 4

ﺩ.ﺇ2,002 per night
Guest favorite

Home in Pittsfield

4.98 out of 5 average rating, 41 reviews

Lake/Mountain View Getaway

Sep 9 – 16

ﺩ.ﺇ755 per night
Guest favorite

Home in Lanesborough

4.92 out of 5 average rating, 25 reviews

Historic Stone Church in The Berkshires

Sep 6 – 13

ﺩ.ﺇ1,290 per night

Quick stats about vacation rentals in Lanesborough

Total rentals

170 properties

Rentals with a pool

110 properties have a pool

Pet-friendly rentals

30 properties allow pets

Family-friendly rentals

110 properties are a good fit for families

Total number of reviews

4.4K reviews

Nightly prices starting at

ﺩ.ﺇ220 before taxes and fees

Frequently Asked Questions

  • What are the most popular amenities for Apartment Rentals in Lanesborough?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 20 homes with air conditioning, over 20 homes with wifi, over 20 homes with a kitchen, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there Lanesborough vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 110 vacation homes with pools in Lanesborough, available on Airbnb. Make a splash and soak up the sun in style!

  • Do condo rentals in Lanesborough have a kitchen?

    Absolutely! We offer over 30 condo rentals with a kitchen in Lanesborough. Enjoy a tailored experience with all the comforts you desire.

  • Do resort rentals in Lanesborough have free parking?

    Absolutely! We offer over 10 resort rentals with free parking in Lanesborough. Enjoy a tailored experience with all the comforts you desire.

  • Are there vacation rentals with a dedicated workspace in Lanesborough?

    Yes! Work meets play with ease at over 60 vacation rentals in Lanesborough featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in apartment rentals in Lanesborough?

    Experience the best of Lanesborough with our apartment rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Lanesborough?

    Four-legged friends are welcome in Lanesborough. Choose from more than 30 vacation rentals for guests traveling with pets.

  • Do house rentals in Lanesborough have air conditioning?

    Absolutely! We offer over 40 house rentals with air conditioning in Lanesborough. Enjoy a tailored experience with all the comforts you desire.

  • Do resort rentals in Lanesborough have wifi?

    Absolutely! We offer over 10 resort rentals with wifi in Lanesborough. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Lanesborough?

    Lanesborough has more than 110 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore