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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

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

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The home you selected

Superhost

Home in Pittsfield

Beautiful Mountain Log Cabin with Scenic Views

8 guests3 bedrooms7 beds2 baths

May 27 – Jun 1

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May 27 – Jun 1

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G$417,612 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$241,737 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$930,679 GYD for 5 nights

for 5 nights

Home in Pittsfield

The Merak Haus – a mid-century retreat

Free cancellation

May 23 – 28

G$453,409 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$272,044 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 15 – 20

G$481,327 GYD for 5 nights

for 5 nights

New place to stay

Superhost

Home in Pittsfield

Hideaway Mountain at Killington

5 beds

May 14 – 19

G$411,646 GYD for 5 nights

for 5 nights

4.89 out of 5 average rating, 63 reviews

Top guest favorite

Home in Pittsfield

Skyeburst | Modern Mtn Home

3 beds

May 14 – 19

G$544,388 GYD for 5 nights

for 5 nights

5.0 out of 5 average rating, 27 reviews

Superhost

Home in Stockbridge

Ski Home Mountain Views Near Killington/Woodstock

6 beds

May 14 – 19

G$230,960 GYD for 5 nights

for 5 nights

New place to stay

Guest favorite

Home in Pittsfield

Killington area home - 4-seasons & hot tub

10 beds

May 14 – 19

G$332,539 GYD for 5 nights

for 5 nights

4.84 out of 5 average rating, 238 reviews

Guest favorite

Home in Pittsfield

Beautiful Cabin w/Hot Tub & Sauna by Killington

5 beds

May 14 – 19

G$289,943 GYD for 5 nights

for 5 nights

4.83 out of 5 average rating, 54 reviews

Top guest favorite

Apartment in Killington

Jack S'Bearo - Slopes, Fireplace, Pool

2 beds

May 14 – 19

G$149,864 GYD for 5 nights

for 5 nights

5.0 out of 5 average rating, 74 reviews

Superhost

Home in Killington

Holiday Haus- AC, game room, near golf

5 beds

May 25 – 30

G$272,283 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 14 – 19

G$162,272 GYD for 5 nights

for 5 nights

5.0 out of 5 average rating, 99 reviews

Guest favorite

Condo in Killington

FirBear - Hot Tub, Pool, FirePlace, Gym

4 beds

May 14 – 19

G$159,075 GYD for 5 nights

for 5 nights

4.95 out of 5 average rating, 133 reviews

Top guest favorite

Apartment in Killington

Hideaway Retreat-Pool Hot Tub FirePlace Location

1 bed

May 14 – 19

G$125,284 GYD for 5 nights

for 5 nights

5.0 out of 5 average rating, 46 reviews

Top guest favorite

Guesthouse in Wallingford

Vermont Home Central to Ski Areas-No Cleaning Fees

Free cancellation

Jun 8 – 13

G$165,852 GYD for 5 nights

for 5 nights

4.98 out of 5 average rating, 687 reviews

Top guest favorite

Condo in Killington

Cozy Condo - next to Killington Resort

2 beds

May 17 – 22

G$133,637 GYD for 5 nights

for 5 nights

4.99 out of 5 average rating, 108 reviews

Superhost

Home in Pittsfield

Green Mountain/Killington Getaway

6 beds

May 14 – 19

G$368,693 GYD for 5 nights

for 5 nights

4.83 out of 5 average rating, 78 reviews

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