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Search results; Over 1,000 places in Pittsfield

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Explore more homes

Superhost

Home in Stockbridge

Ski Home Mountain Views Near Killington/Woodstock

6 beds

1–6 Jun

₹84,158 for 5 nights

for 5 nights

5.0 out of 5 average rating, 3 reviews

Guest favourite

Cabin in Pittsfield

Tiny Vermont Cabin!

Free cancellation

1–6 Jun

₹97,606 for 5 nights

for 5 nights

4.98 out of 5 average rating, 155 reviews

Guest favourite

Home in Pittsfield

Beautiful Cabin w/Hot Tub & Sauna by Killington

5 beds

1–6 Jun

₹94,632 for 5 nights

for 5 nights

4.84 out of 5 average rating, 55 reviews

Home in Pittsfield

The Merak Haus – a mid-century retreat

Free cancellation

1–6 Jun

₹1,88,275 for 5 nights

for 5 nights

New place to stay

Home in Rochester

New! Serene Architect-Designed Vermont Chalet

Free cancellation

1–6 Jun

₹1,99,868 for 5 nights

for 5 nights

New place to stay

Top guest favourite

Apartment in Killington

Walk/Bike to Snowshed Lift 2BR @ Mt. Green Resort!

4 beds

8–13 Jun

₹39,638 for 5 nights

for 5 nights

4.95 out of 5 average rating, 230 reviews

Home in Pittsfield

4-Season Mountain Getaway Near Killington

Free cancellation

8–13 Jul

₹3,86,458 for 5 nights

for 5 nights

Cabin in Pittsfield

Killington/PICO Ski House Hot Tub & Fast Wifi

Free cancellation

1–6 Jun

₹98,993 for 5 nights

for 5 nights

4.71 out of 5 average rating, 164 reviews

Guest favourite

Home in Pittsfield

Hideaway Mountain at Killington

5 beds

1–6 Jun

₹1,70,438 for 5 nights

for 5 nights

4.89 out of 5 average rating, 63 reviews

Top guest favourite

Home in Bethel

Vermont private retreat with gorgeous views.

Free cancellation

26–31 Aug

₹77,894 for 5 nights

for 5 nights

4.96 out of 5 average rating, 98 reviews

Guest favourite

Chalet in Stockbridge

Gnome Home Mountain Ski Chalet w/Sauna Killington

6 beds

6–11 Jun

₹1,25,548 for 5 nights

for 5 nights

4.96 out of 5 average rating, 126 reviews

Guest favourite

Room in Brandon

Stay with EvvaRetired,

Low rates

16–21 Jun

₹24,773 for 5 nights

for 5 nights

4.82 out of 5 average rating, 326 reviews

Room in Rochester

Stay with Carol

The Ice Castle Adventure Air B and B

1–6 Jun

₹29,727 for 5 nights

for 5 nights

New place to stay

Guest favourite

Flat in Killington

New Resort Condo Close to Lifts

Free cancellation

1–6 Jun

₹49,050 for 5 nights

for 5 nights

5.0 out of 5 average rating, 12 reviews

Top guest favourite

Apartment in Mendon

¤5-15 Mins to Ski Slopes | Fast WiFi | Fireplace¤

Free cancellation

1–6 Jun

₹53,113 for 5 nights

for 5 nights

4.94 out of 5 average rating, 36 reviews

Guest favourite

Apartment in Killington

Hike bike golf 1 bedroom 1 nght Ok shuttle

3 beds

1–6 Jun

₹49,447 for 5 nights

for 5 nights

4.93 out of 5 average rating, 454 reviews

Guest favourite

Apartment in Killington

Wood-Burning Fireplace/Dog-Friendly/Spa Onsite/AC

4 beds

1–6 Jun

₹78,778 for 5 nights

for 5 nights

4.94 out of 5 average rating, 256 reviews

Guest favourite

Home in Pittsfield

VT Cabin, close to Killington Mountain and lakes.

Free cancellation

1–6 Jun

₹1,82,824 for 5 nights

for 5 nights

4.97 out of 5 average rating, 38 reviews

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