The Vacation Rental Search Engine

Over 1.8 million vacation home listings in a single click!

Where do you want to go?

Towns near Pittsfield · Show vacation rentals in all these towns
Sort by:

Search results: 20 vacation rentals in Pittsfield!

MADISON BROOK HOME - Photo YAHOO.otalo.hkqns5a74p_Arr - Click to see details about this awesome vacation rental...
«   1  of  7   »
3 BR / 2 BA
$2,000-6,250/wk
Inquire about this vacation rental at
RIVERSIDE FARM - ELEGANT RURAL ESTATE FOR WEDDINGS AND RETREATS - Photo YAHOO.otalo.op03nx8uyi_Arr - Click to see details about this awesome vacation rental...
«   1  of  16   »
10 BR / 6 BA
$1,750-10,500/wk
Inquire about this vacation rental at
ON THE KILLINGTON SIDE PITTSFIELD VILLAGE NEAR RIVERSIDE FARM - Photo YAHOO.otalo.uzssrs5vhc_Arr - Click to see details about this awesome vacation rental...
«   1  of  15   »
3 BR / 2 BA
$4,000/wk
Inquire about this vacation rental at
KILLINGTON AREA SKI HOUSE - GREAT VALUE! - Photo YAHOO.otalo.ilk2nsl59l_Arr - Click to see details about this awesome vacation rental...
«   1  of  12   »
3 BR / 2 BA
$770/wk
Inquire about this vacation rental at
NEWLY BUILT KILLINGTON VERMONT SKI HOUSE - Photo YAHOO.otalo.kc298t7kit_Arr - Click to see details about this awesome vacation rental...
«   1  of  12   »
5 BR / 3 BA
$2,300/wk
Inquire about this vacation rental at
SKIERS AND SNOWMOBILERS DREAM CHALET - Photo YAHOO.otalo.vk1awxxzvx_Arr - Click to see details about this awesome vacation rental...
«   1  of  18   »
3 BR / 2 BA
$1,450/wk
Inquire about this vacation rental at
KILLINGTON SKI HOUSE - PITTSFIELD REGION - Photo YAHOO.otalo.chvbbe3hgj_Arr - Click to see details about this awesome vacation rental...
«   1  of  12   »
4 BR / 2 BA
$2,100-4,200/wk
Inquire about this vacation rental at
15 BR AMEE LODGE - KILLINGTON AREA SKI HOUSE. PERFECT FOR REUNIONS & RETREATS - Photo YAHOO.otalo.xb4mnwltmk_Arr - Click to see details about this awesome vacation rental...
«   1  of  24   »
15 BR / 13 BA
$665-21,910/wk
Inquire about this vacation rental at
WELCOME TO BEAR BUM HOLLOW! BEAUTIFUL MOUNTAIN HOME - KILLINGTON - Photo YAHOO.otalo.iw1zywtcc2_Arr - Click to see details about this awesome vacation rental...
«   1  of  12   »
4 BR / 2 BA
$750-2,900/wk
Inquire about this vacation rental at
VT Studio, Lovers/Ski/Hike/4 Sale - Photo YAHOO.otalo.yili0z1rki_Arr - Click to see details about this awesome vacation rental...
«   1  of  31   »
1 BR / 1 BA
$875/wk
Inquire about this vacation rental at
THE RIVER HOUSE - Photo YAHOO.otalo.ke6xj07tjq_Arr - Click to see details about this awesome vacation rental...
«   1  of  7   »
5 BR / 3 BA
$1,550-6,000/wk
Inquire about this vacation rental at
2.5 MI TO RIVERSIDE FARM! CUSTOM BUILT HOME! WIFI! DISH NETWORK! - Photo YAHOO.otalo.aofuxkqiu4_Arr - Click to see details about this awesome vacation rental...
«   1  of  23   »
5 BR / 2 BA
$1,750/wk
Inquire about this vacation rental at
LORI AND DEAN'S KILLINGTON SKI HOUSE WITH WI-FI - Photo YAHOO.otalo.hpzaom1mwq_Arr - Click to see details about this awesome vacation rental...
«   1  of  24   »
3 BR / 2 BA
$450-1,800/wk
Inquire about this vacation rental at
Spacious valley view home- fireplace, deck, spa room, wet... - Photo YAHOO.otalo.jttan2wtxe_Arr - Click to see details about this awesome vacation rental...
«   1  of  20   »
4 BR / 4 BA
$1,350-7,163/wk
Inquire about this vacation rental at
SHANGRI-LA - OUTDOOR HOT TUB VIEWS TO KILLINGTON PEAK - Photo YAHOO.otalo.ov1elt8xkr_Arr - Click to see details about this awesome vacation rental...
«   1  of  24   »
3 BR / 3 BA
$2,000-7,000/wk
Inquire about this vacation rental at
PITTSFIELD STREAMSIDE MOUNTAIN HOME - Photo YAHOO.otalo.esgscqq9gr_Arr - Click to see details about this awesome vacation rental...
«   1  of  7   »
3 BR / 3 BA
$1,225/wk
Inquire about this vacation rental at
FOUR SEASON KILLINGTON GETAWAY! - Photo YAHOO.otalo.vv50ubhzxz_Arr - Click to see details about this awesome vacation rental...
«   1  of  24   »
3 BR / 1 BA
$1,750/wk
Inquire about this vacation rental at
MOUNTAIN CHALET - KILLINGTON AREA - Photo YAHOO.otalo.rsfzbfc3mo_Arr - Click to see details about this awesome vacation rental...
«   1  of  12   »
4 BR / 2 BA
$1,050-2,800/wk
Inquire about this vacation rental at
Charming, spacious condo- full kitchen, hot tub, fireplace, near amenities - Photo YAHOO.otalo.rivnyjdc68_Arr - Click to see details about this awesome vacation rental...
«   1  of  11   »
2 BR / 1 BA
$1,019-2,577/wk
Inquire about this vacation rental at
Peaceful Home Surrounded By Nature - Photo YAHOO.otalo.xjetl8khjk_Arr - Click to see details about this awesome vacation rental...
«   1  of  9   »
4 BR / 3 BA
$1,057/wk
Inquire about this vacation rental at

About Pittsfield, Vermont

Pittsfield is a town in Rutland County, Vermont, United States. The population was 427 at the 2000 census. It is site of the annual Pittsfield Snowshoe Race.

Visit Wikipedia for more information about Pittsfield, Vermont.  

Things To Do in Pittsfield from

  • Pico Mountain At Killington
  • , Root's Ski & Snowboard Shop
  • , Outback Pizza
  • , On the Rocs Lounge
  • , Wobbly Barn Steakhouse
  • , Clear River Tavern
  • , The Lookout Tavern
  • , McGrath's Irish Pub
  • , Green Mountain National
  • , Pickle Barrel

Restaurants in Pittsfield

  • Rochester Cafe
  • , The Snow Angel Tavern
  • , Maple Sugar & Vermont Spice
  • , Original General Store
  • , Sandy's Books and Bakery
  • , Clear River Tavern
  • , Red Clover Restaurant & Tavern
  • , The Foundry at Summit Pond
  • , The Garlic
  • , Wild Fern