Pittsfield Vacation Rentals, Houses & More


1 - 38 of 343

View larger map

Areas near Pittsfield

1 / 27

Charming mountain farmhouse

  • 4
  • 9
  • 2 nights min

$150

Details

Great rentals within 20 miles that match your search

1 / 27

LUXURY SkiOnSkiOff- The Navillus House off Great Eastern Ski Trail!

  • 4
  • 16
  • Min stay varies

$326

Details

1 / 22

SUMMER SALE VT 2 Bd 1&1/2 B Condo $89 av nt. Four Season Resort Condo Sleeps 6

  • 2
  • 6
  • Min stay varies

$89

Details

1 / 16

One Bedroom furnished apartment & hotel facilities

  • 1
  • 2
  • 3 nights min

$201

Details

1 / 24

Upper unit of Chalet, minutes to Killington, Okemo or Woodstock

  • 2
  • 6
  • 2 nights min

$351

Details

1 / 4

One bedroom condo at Killington

  • 1
  • 4
  • 7 nights min

$51

Details

1 / 8

Luxury vacation home in Killington

  • 4
  • 8
  • 2 nights min

$226

Details

1 / 19

Luxury Apartment at Slopeside Estate Ski On Ski Off Great Eastern Ski Trail

  • 1
  • 6
  • Min stay varies

$150

Details

1 / 11

Premier Ski-in / Ski-out - 3 Bed, Sunrise Mountain

  • 3
  • 10
  • 2 nights min

$651

Details

1 / 4

Ski Killington Vermont

  • 1
  • 6
  • 7 nights min

$191

Details

1 / 29

Mt Green 1-B9

  • 1
  • 4
  • Min stay varies

$144

Details

1 / 28

Woods Village 10

  • 2
  • 6
  • Min stay varies

$191

Details

1 / 28

Mt Green 3-C8

  • 1
  • 4
  • Min stay varies

$144

Details

1 / 22

Colony Club C11

  • 4
  • 8
  • Min stay varies

Inquire for Rates

Details

1 / 28

Hakuna Matata

  • 3
  • 6
  • Min stay varies

$191

Details

1 / 34

Mt Green 1-D5

  • 3
  • 8
  • Min stay varies

$247

Details

1 / 34

Mt Green 1-D2

  • 2
  • 6
  • Min stay varies

$183

Details

1 / 8

Lake Dunmore House

  • 2
  • 6
  • 7 nights min

$214

Details

1 / 9

The Kings Pines Luxury Townhomes

  • 5
  • 10
  • Min stay varies

$300

Details

1 / 29

Mt Green 3-C4

  • 2
  • 8
  • Min stay varies

$183

Details

1 / 39

Heavenly on Killington Access Road Brand New House

  • 7
  • 16
  • Min stay varies

$501

Details

1 / 6

Killington Furnished Private Apartment

  • 2
  • 3
  • Min stay varies

$31

Details

1 / 16

THE MATTERHORN HOUSE- ski on ski off Great Eastern Ski Trail

  • 4
  • 19
  • Min stay varies

$326

Details

1 / 19

Luxury One Bedroom Condominium #1 SkiOnSkiOff Great Eastern Ski Trail!

  • 1
  • 6
  • Min stay varies

$125

Details

1 / 25

Unit 1 - New House On Killington Access Road

  • 4
  • 10
  • 2 nights min

$450

Details

1 / 36

The Lodges at Bear Mountain Luxury ski-on/ski-off 3 bedroom all en-suite

  • 3
  • 8
  • Min stay varies

$295

Details

1 / 38

Woods Resort Unit V29 ~ RA147304

  • 2
  • 6
  • Min stay varies

$386

Details

1 / 24

Luxury Topridge Unit K6 SkiOnSkiOff Sundog Trail-Bear Mountain in Killington!

  • 4
  • 12
  • Min stay varies

$326

Details

1 / 23

Killington Secluded 6 Acre Mtn Property w/GameRoom

  • 6
  • 32
  • Min stay varies

$399

Details

1 / 16

Killington area ski house

  • 5
  • 11
  • 2 nights min

$450

Details

1 / 33

Hawk Landing ~ RA147231

  • 3
  • 6
  • Min stay varies

$386

Details

1 / 28

Charming condo w/ shared hot tub - near golf, ski trails & fishing!

  • 2
  • 8
  • Min stay varies

$99

Details

1 / 26

Sweet Life

  • 3
  • 20
  • Min stay varies

$363

Details

1 / 56

Lookout ~ RA80756

  • 3
  • 6
  • Min stay varies

$351

Details

1 / 11

PittsfieldChalet

  • 4
  • 8
  • Min stay varies

$300

Details

1 / 56

Blue Diamond ~ RA80778

  • 4
  • 11
  • Min stay varies

$435

Details

1 / 30

Blue Diamond

  • 4
  • 11
  • Min stay varies

$280

Details

1 / 24

Sweet Life ~ RA80770

  • 3
  • 20
  • Min stay varies

$551

Details

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more
See only the properties that can be booked online with Payment Protection.
Learn more