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Search results; Over 1,000 places in Pittsfield

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Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

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Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

Prices include all fees

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The home you selected

Guest favorite

Home in Pittsfield

Beautiful Cabin w/Hot Tub & Sauna by Killington

8 guests3 bedrooms5 beds2 baths

May 15 – 20

More

May 15 – 20

More

G$290,435 GYD for 5 nights

for 5 nights

Explore more homes

Guest favorite

Cabin in Pittsfield

Tiny Vermont Cabin!

Free cancellation

May 30 – Jun 4

G$240,715 GYD for 5 nights

for 5 nights

4.98 out of 5 average rating, 155 reviews

Home in Pittsfield

4-Season Mountain Getaway Near Killington

Free cancellation

Jul 8 – 13

G$932,259 GYD for 5 nights

for 5 nights

Superhost

Home in Killington

Come experience VT Living

Free cancellation

Jun 1 – 6

G$326,052 GYD for 5 nights

for 5 nights

New place to stay

Home in Pittsfield

The Merak Haus – a mid-century retreat

Free cancellation

May 23 – 28

G$454,179 GYD for 5 nights

for 5 nights

New place to stay

Guest favorite

Home in Pittsfield

A million-dollar view near Killington on 60 acres.

6 beds

Jun 2 – 7

G$272,506 GYD for 5 nights

for 5 nights

4.85 out of 5 average rating, 106 reviews

Home in Rochester

New! Serene Architect-Designed Vermont Chalet

7 beds

May 16 – 21

G$482,144 GYD for 5 nights

for 5 nights

New place to stay

Top guest favorite

Home in Pittsfield

Skyeburst | Modern Mtn Home

3 beds

May 16 – 21

G$545,313 GYD for 5 nights

for 5 nights

5.0 out of 5 average rating, 27 reviews

Superhost

Home in Pittsfield

Hideaway Mountain at Killington

5 beds

May 15 – 20

G$411,149 GYD for 5 nights

for 5 nights

4.89 out of 5 average rating, 63 reviews

Guest favorite

Home in Pittsfield

Killington area home - 4-seasons & hot tub

10 beds

May 15 – 20

G$333,103 GYD for 5 nights

for 5 nights

4.84 out of 5 average rating, 238 reviews

Superhost

Home in Stockbridge

Ski Home Mountain Views Near Killington/Woodstock

6 beds

May 19 – 24

G$233,236 GYD for 5 nights

for 5 nights

New place to stay

Top guest favorite

Guest suite in Stockbridge

Studio Suite with Vermont Style & Amazing Views

1 bed

May 15 – 20

G$162,548 GYD for 5 nights

for 5 nights

5.0 out of 5 average rating, 99 reviews

Top guest favorite

Tiny home in Pittsford

Le Petit Maison d 'Allaire

Free cancellation

Jun 1 – 6

G$126,690 GYD for 5 nights

for 5 nights

5.0 out of 5 average rating, 8 reviews

Guest favorite

Home in Pittsfield

Mountain Top - Fresh Pond - Killington - Hot Tub

9 beds

May 15 – 20

G$764,932 GYD for 5 nights

for 5 nights

5.0 out of 5 average rating, 23 reviews

Guest favorite

Chalet in Stockbridge

Killington ski house winter MTbike -new jacuzzi

6 beds

May 15 – 20

G$229,478 GYD for 5 nights

for 5 nights

4.92 out of 5 average rating, 181 reviews

Guest favorite

Condo in Killington

Pico discounted 1 bedroom 1 nght Ok shuttle

3 beds

May 16 – 21

G$144,620 GYD for 5 nights

for 5 nights

4.93 out of 5 average rating, 453 reviews

Guest favorite

Apartment in Killington

New Resort Condo Close to Lifts

2 beds

May 15 – 20

G$123,107 GYD for 5 nights

for 5 nights

5.0 out of 5 average rating, 12 reviews

Superhost

Home in Killington

Holiday Haus- AC, game room, near golf

5 beds

May 25 – 30

G$277,527 GYD for 5 nights

for 5 nights

New place to stay

Guest favorite

Home in Pittsfield

Chalet Suite | 2BR+Loft (Secure Mtn Bike Storage)

4 beds

May 16 – 21

G$190,039 GYD for 5 nights

for 5 nights

5.0 out of 5 average rating, 12 reviews

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