Search results; Over 1,000 places in Pittsfield

Home in Pittsfield
The Merak Haus – a mid-century retreat
Free cancellation
23–28 May
₹1,87,462 for 5 nights, originally ₹2,23,486
for 5 nights
New place to stay
Home in Rochester
New! Serene Architect-Designed Vermont Chalet
7 beds
9–14 May
₹1,74,458 for 5 nights
for 5 nights
New place to stay
Home in Pittsfield
4-Season Mountain Getaway Near Killington
Free cancellation
8–13 Jul
₹3,84,789 for 5 nights, originally ₹4,47,937
for 5 nights
Superhost
Home in Stockbridge
Ski Home Mountain Views Near Killington/Woodstock
6 beds
12–17 May
₹90,378 for 5 nights, originally ₹1,12,331
for 5 nights
New place to stay
Superhost
Home in Killington
Holiday Haus- AC, game room, near golf
5 beds
25–30 May
₹1,07,642 for 5 nights
for 5 nights
New place to stay
Guest favourite
Home in Pittsfield
A million-dollar view near Killington on 60 acres.
6 beds
11–16 May
₹1,09,517 for 5 nights
for 5 nights
4.85 out of 5 average rating, 106 reviews
Superhost
Cabin in Killington
Ideal Killington Escape! Hot tub & 2 fireplaces
Free cancellation
31 May – 5 Jun
₹1,30,868 for 5 nights, originally ₹1,58,975
for 5 nights
New place to stay
Guest favourite
Home in Pittsfield
Beautiful Cabin w/Hot Tub & Sauna by Killington
5 beds
11–16 May
₹1,11,984 for 5 nights
for 5 nights
4.83 out of 5 average rating, 54 reviews
Guest favourite
Chalet in Stockbridge
Killington ski house winter MTbike -new jacuzzi
6 beds
8–13 May
₹94,717 for 5 nights, originally ₹1,21,417
for 5 nights
4.92 out of 5 average rating, 181 reviews
Top guest favourite
Home in Pittsfield
Curated Killington - 2 Living Rooms - Sleeps 10
6 beds
9–14 May
₹1,49,574 for 5 nights
for 5 nights
5.0 out of 5 average rating, 40 reviews
Guest favourite
Home in Pittsfield
The Getaway: Hot Tub 4BR, Killington Discounts!
6 beds
8–13 May
₹1,37,636 for 5 nights
for 5 nights
4.92 out of 5 average rating, 12 reviews
Guest favourite
Home in Pittsfield
Killington area home - 4-seasons & hot tub
10 beds
8–13 May
₹1,37,488 for 5 nights, originally ₹1,51,601
for 5 nights
4.84 out of 5 average rating, 238 reviews
Home in Pittsfield
Babbling brooks and serenity
16 beds
9–14 May
₹1,92,396 for 5 nights
for 5 nights
4.69 out of 5 average rating, 16 reviews
Superhost
Home in Stockbridge
Ski, snow mobile, hiking, fun on slopes & trails!
2 queen beds
12–17 May
₹66,106 for 5 nights
for 5 nights
4.77 out of 5 average rating, 84 reviews
Guest favourite
Chalet in Stockbridge
Gnome Home Mountain Ski Chalet w/Sauna Killington
6 beds
18–23 May
₹1,26,783 for 5 nights
for 5 nights
4.96 out of 5 average rating, 126 reviews
Superhost
Home in Pittsfield
Hideaway Mountain at Killington
5 beds
8–13 May
₹1,69,702 for 5 nights
for 5 nights
4.89 out of 5 average rating, 63 reviews
Guest favourite
Home in Pittsfield
Chalet Suite | 2BR+Loft (Secure Mtn Bike Storage)
4 beds
8–13 May
₹78,438 for 5 nights
for 5 nights
5.0 out of 5 average rating, 12 reviews
Cabin in Pittsfield
Killington/PICO Ski House Hot Tub & Fast Wifi
4 beds
8–13 May
₹98,566 for 5 nights
for 5 nights
4.71 out of 5 average rating, 163 reviews