Vacation rentals in Lanesborough

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Top-rated holiday rentals in Lanesborough

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

Guest favourite
Home in Lanesborough
Ski at Historic Stone Church in The Berkshires
Hinterland Hall was built in 1836 by the Saint Luke's Episcopal Parish and joined the National Register of Historic Places in 1972. Ripe with history and impeccable beauty, Ian & Jane purchased the old stone church in May of 2021, completing an extensive restoration process in accordance with the Massachusetts Historical Commission. It is with great pleasure that we open our doors to you for a wondrous stay. Follow us @hinterlandhall Please inquire about weddings & events.
10–17 Jun
$671 NZD per night
4.92 out of 5 average rating, 25 reviews
Guest favourite
Cottage in Lanesborough
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.
27 Mar – 3 Apr
$331 NZD per night
4.93 out of 5 average rating, 219 reviews
Guest favourite
Apartment in Lanesborough
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.
8–15 Apr
$295 NZD per night
5.0 out of 5 average rating, 21 reviews

Popular amenities for Lanesborough holiday 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 holiday rentals in Lanesborough

Guest favourite
Home in Lanesborough
Cozy Cottage in Berkshires: Minutes to Jiminy Peak
3–10 May
$449 NZD per night
4.98 out of 5 average rating, 54 reviews
Guest favourite
Home in Lanesborough
Elmwood Farmhouse
25 Feb – 4 Mar
$563 NZD per night
4.9 out of 5 average rating, 98 reviews
Superhost
Cabin in Lanesborough
Cozy stream-side cabin
23–30 Nov
$357 NZD per night
4.83 out of 5 average rating, 52 reviews
Guest favourite
Home in Lanesborough
Lake Views, Lrg Open Grand Room+Kitchen, Hot Tub
22–29 Mar
$853 NZD per night
5.0 out of 5 average rating, 31 reviews
Guest favourite
Home in Pittsfield
Lake/Mountain View Getaway
26 Dec – 2 Jan
$387 NZD per night
4.97 out of 5 average rating, 39 reviews
Guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
21–28 Apr
$202 NZD per night
4.99 out of 5 average rating, 101 reviews
Guest favourite
Home in Lanesborough
Contemporary Home Near Williams College.
21–28 Feb
$1,024 NZD per night
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Lanesborough
Chic Berkshire Retreat by Evergreen Home
18–25 Aug
$790 NZD per night
4.94 out of 5 average rating, 18 reviews
Guest favourite
Condo in Hancock
Jiminy Peak Country Inn - ski in/out condo MT view
4–11 Jul
$261 NZD per night
4.9 out of 5 average rating, 51 reviews
Guest favourite
Home in Pittsfield
Berkshire Pontoosuc Lake- Modern and Updated
18–25 Feb
$1,317 NZD per night
4.97 out of 5 average rating, 94 reviews
Guest favourite
Barn in Williamstown
Silo Suite with Berkshire Mountain Views!
4–11 Sep
$426 NZD per night
5.0 out of 5 average rating, 54 reviews
Guest favourite
Home in Cheshire
The Berkshires Hummingbird House
10–17 May
$354 NZD per night
5.0 out of 5 average rating, 21 reviews

Quick stats about holiday 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

$99 NZD before taxes and fees

Destinations to explore