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Guest favorite
Cabin in Lanesborough
Glamping in the Berkshires w/ car charging station
10 guests3 bedrooms8 beds2 baths
Jun 18 – 23
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Jun 18 – 23
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ﺩ.ﺇ8,395 for 5 nights
for 5 nights

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Top guest favorite
Home in Lanesborough
Mountain Serenity 20 Acres, Hot Tub, Jiminy<10min
5 beds
May 28 – Jun 2
ﺩ.ﺇ13,130 for 5 nights
for 5 nights
5.0 out of 5 average rating, 11 reviews
Guest favorite
Home in Lanesborough
Historic Stone Church in The Berkshires
1 bed
May 17 – 22
ﺩ.ﺇ7,748 for 5 nights
for 5 nights
4.96 out of 5 average rating, 50 reviews
Guest favorite
Apartment in Lanesborough
Cozy Rustic Apt. in 18th c. Berkshire Farmhouse
2 beds
Jun 1 – 6
ﺩ.ﺇ3,035 for 5 nights
for 5 nights
4.89 out of 5 average rating, 126 reviews
Guest favorite
Room in Cheshire
Stay with Laura NiraOrganic dayspa owner,
Private sweet sunny room, tranquil home
Jun 1 – 6
ﺩ.ﺇ1,326 for 5 nights
for 5 nights
5.0 out of 5 average rating, 5 reviews
Room in Lanesborough
Stay with Carlton
1bed rm. skier’s bliss 2 miles only 1 rd to slopes
May 19 – 24
ﺩ.ﺇ2,290 for 5 nights
for 5 nights
4.79 out of 5 average rating, 68 reviews
Guest favorite
Cottage in Lanesborough
Stone School Cottage
4 beds
May 17 – 22
ﺩ.ﺇ3,766 for 5 nights
for 5 nights
4.93 out of 5 average rating, 242 reviews
Top guest favorite
Home in Lanesborough
The Pond House
Free cancellation
May 28 – Jun 2
ﺩ.ﺇ4,658 for 5 nights
for 5 nights
4.94 out of 5 average rating, 36 reviews
Guest favorite
Home in Lanesborough
Lakefront Home on Ponstoosuc Lake, The Berkshires
4 beds
May 18 – 23
ﺩ.ﺇ7,663 for 5 nights
for 5 nights
5.0 out of 5 average rating, 9 reviews
Top guest favorite
Home in Lanesborough
Mountain Blossom Retreat by Evergreen Home
Free cancellation
Jun 22 – 27
ﺩ.ﺇ20,427 for 5 nights
for 5 nights
5.0 out of 5 average rating, 20 reviews
Top guest favorite
Apartment in Pittsfield
The sweet place in the beautiful Berkshires!
3 beds
Jun 13 – 18
ﺩ.ﺇ2,911 for 5 nights
for 5 nights
4.96 out of 5 average rating, 80 reviews
Home in Lanesborough
Berkshires: Nature, New Home !
Free cancellation
May 24 – 29
ﺩ.ﺇ11,946 for 5 nights
for 5 nights
New place to stay
Guest favorite
Condo in Hancock
SKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit2
6 beds
May 17 – 22
ﺩ.ﺇ5,037 for 5 nights
for 5 nights
4.98 out of 5 average rating, 44 reviews
Top guest favorite
Guest suite in Dalton
Berkshires getaway: nature, culture & relaxation
Free cancellation
Jul 11 – 16
ﺩ.ﺇ3,724 for 5 nights
for 5 nights
4.98 out of 5 average rating, 65 reviews
Guest favorite
Home in Lanesborough
Contemporary Berkshires Home-5 Mins to Jiminy Peak
3 beds
May 27 – Jun 1
ﺩ.ﺇ9,987 for 5 nights
for 5 nights
5.0 out of 5 average rating, 14 reviews
Cabin in New Ashford
Rustic Cabin with Loft
3 beds
May 17 – 22
ﺩ.ﺇ3,529 for 5 nights
for 5 nights
5.0 out of 5 average rating, 3 reviews
Guest favorite
Home in Pittsfield
Berkshire Getaway Ranch 3 acres + saltwater pool
3 beds
May 17 – 22
ﺩ.ﺇ6,565 for 5 nights
for 5 nights
4.96 out of 5 average rating, 71 reviews
Top guest favorite
Home in Cheshire
The Berkshires Hummingbird House
4 beds
May 18 – 23
ﺩ.ﺇ5,747 for 5 nights
for 5 nights
5.0 out of 5 average rating, 51 reviews
Guest favorite
Apartment in Pittsfield
Comfy Quaint Tavern
1 queen bed
May 23 – 28
ﺩ.ﺇ3,616 for 5 nights
for 5 nights
5.0 out of 5 average rating, 37 reviews