Houses Pittsfield

Updating...

age 0-16
218 Results

Relevance

Price: low to high

Price: high to low

Reviews

218 houses

PARADISE on EARTH! - Historic 4BR Farmhouse

West Halifax house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Rental types Secure parking

All filters match

Price per night from

$326

Berkshire house w/ fireplace, A/C, WiFi & laundry

Plainfield house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

“Peaceful country home” Beautiful, welcoming home in a perfect location. Warm and inviting living room; bright, airy bedrooms.

Match: Rental types Secure parking

All filters match

Price per night from

$234

Stowe Stone Cottage in pristine Sterling Forest

Stowe house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Rental types Secure parking

All filters match

Price per night from

$372

Village Farmhouse - mins to GMHA, Okemo, Killington. Pet-friendly.

Reading house

  • 4 bedrooms
  • 1 bathroom
  • sleeps 8

Match: Rental types Secure parking

All filters match

Price per night from

$286

These homes match some but not all of your filters. Clear all filters

OWL'S NEST LODGING

Conway apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Rental types, Secure parking

1 of 2 filters match

Price per night from

$196

The I.B. Munson House Inn - All Bedrooms

Wallingford b&b

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Rental types, Secure parking

1 of 2 filters match

Price per night from

$715

Cozy Guest Suite minutes from Amherst and UMASS

Amherst guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Rental types, Secure parking

1 of 2 filters match

Price per night from

$159

Hugging Bear Inn RENT ENTIRE INN

Chester b&b

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 18

1 of 2 match: Rental types, Secure parking

1 of 2 filters match

Price per night from

$1,230

Spectacular 50 miles Year Round Mountain View - 3+ BR Townhouse

Peru townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 2 minutes

1 of 2 match: Rental types, Secure parking

1 of 2 filters match

Price per night from

$338

5 mins to Mt Snow Free Shuttle Ski Home

Dover townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Secure parking

1 of 2 filters match

Price per night from

$229

1 of 2 match: Rental types, Secure parking

1 of 2 filters match

Price per night from

$488

Vermont Cottage on Lake Amherst 6 Bedrooms 4 Bathrooms

Plymouth cottage

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Rental types, Secure parking

1 of 2 filters match

Price per night from

$801

Fall dates So Vt Mtn Cabn where memories are made and guaranteed to come back.

Mount Tabor log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 20 minutes

1 of 2 match: Rental types, Secure parking

1 of 2 filters match

Price per night from

$235

Cute two bedroom

Williamsburg apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Rental types, Secure parking

1 of 2 filters match

Price per night from

$138

Whispers of the North

West Wardsboro house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 14

1 of 2 match: Secure parking, Rental types

1 of 2 filters match

Price per night from

$252

1 of 2 match: Secure parking, Rental types

1 of 2 filters match

Price per night from

$1,166

Charming Rental 3 Miles From Mt. Mansfield

Stowe house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Secure parking, Rental types

1 of 2 filters match

Price per night from

$515

Flight's End-A Country Home with Babbling Brook

Hawley house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Perfect getaway” We spent few days there. It is very quiet and private. We loved the retro look. Looking forward going there again. It was New Year's eve we were hoping for.

1 of 2 match: Secure parking, Rental types

1 of 2 filters match

Price per night from

$218

Church sanctuary

West Dummerston house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Secure parking, Rental types

1 of 2 filters match

Price per night from

$298

1 of 2 match: Secure parking, Rental types

1 of 2 filters match

Price per night from

$429

Live & Breathe VT- Village Home, Yoga Studio, Ski!

Jamaica house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

1 of 2 match: Secure parking, Rental types

1 of 2 filters match

Price per night from

$286

Vermont Country Lake House

Ludlow house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Secure parking, Rental types

1 of 2 filters match

Price per night from

$286

Killington Mountain Slopeside Home

Killington house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

“Ski home at Killington” We've been here for 10 days in late January. Wonderful place. Excellent home. We were two families with 4 aDT, CHD 4 with 6.9, 11 and 14 years. We left and came back home from skiing. We used the heated pool at the sport center. the hot tub ... We skate on the frozen pond. Although we are not accustomed to the cold (-13 F/ -25 C) for being Brazilians, we enjoyed a lot. Thank you!

Responds fast! avg. 38 minutes

1 of 2 match: Secure parking, Rental types

1 of 2 filters match

Price per night from

$972

Stowe Area #1 Luxury Inn - Private Rental

Stowe house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

1 of 2 match: Secure parking, Rental types

1 of 2 filters match

Price per night from

$1,716

Stowe House. Luxurious. King Bed, Sauna, Wifi.

Stowe house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

“Lovely House in a Great Location” I've been to Stowe a few times. Geographically speaking, it's a fairly large and spread out area with homes all over the place. This house was perfectly located a short 2 minute drive form downtown Stowe. It's also on the Waterbury side, which makes for a shorter trip over there. The house was very clean and modern, while still maintaining the charm of a Vermont country home. It was fully stocked with everything you'd need (linens, dishes, paper products, cleaning supplies, etc). The layout was unique, as you come in at ground level and the multiple floors eventually give way to an open kitchen/dining/common area. There was also a loft on this top floor, which would be great fun for kids. One important thing to note - there are a lot of stairs. You have to go up a bunch of stairs to get from the driveway to the house, and then within the house you're constantly going up and down the stairs due to the layout. It's by no means exhausting, but just be prepared to get a little more exercise than you would probably expect. Also - bring your bug spray if you're sitting outside after dark! I'd strongly recommend this house for either a couple or a family. Great value in a very nice home in an excellent location.

1 of 2 match: Secure parking, Rental types

1 of 2 filters match

Price per night from

$515

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Hinsdale house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Secure parking, Rental types

1 of 2 filters match

Price per night from

$218

1 of 2 match: Secure parking, Rental types

1 of 2 filters match

Price per night from

$401

Vermont Log Home On 21 Acres Btwn Okemo/killington

Mount Holly house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 14

1 of 2 match: Secure parking, Rental types

1 of 2 filters match

Price per night from

$429

Stowe Vermont Winter Season Rental

Stowe house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

1 of 2 match: Secure parking, Rental types

1 of 2 filters match

Price per night from

$858

Charming Old Vermont Farmhouse: Weekly Rental

Richmond house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Secure parking, Rental types

1 of 2 filters match

Price per night from

$286

Farmhouse Rustic Lux on 10 acres w/ swimming pond

Bridgewater house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 22

1 of 2 match: Secure parking, Rental types

1 of 2 filters match

Price per night from

$744

A Family Place

Bondville house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Secure parking, Rental types

1 of 2 filters match

Price per night from

$412

Vermont 1828 Reunion House, sleeps 16 5 miles to Okemo

Proctorsville house

  • 8 bedrooms
  • 4 bathrooms
  • sleeps 16

1 of 2 match: Secure parking, Rental types

1 of 2 filters match

Price per night from

$458

Family Lodge btwn Stratton Mountain & Mt. Snow

Stratton Mountain house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 11

1 of 2 match: Secure parking, Rental types

1 of 2 filters match

Price per night from

$681

Killington Vermont - 4 Bedroom, 2 Bath. Right in the heart of ski country!

Killington house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Secure parking, Rental types

1 of 2 filters match

Price per night from

$858

Charming 'Swiss Chalet' Ski Cabin Near Mount Snow

Wilmington house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Secure parking, Rental types

1 of 2 filters match

Price per night from

$201

Oma"s Kottage

Ludlow house

  • 6 bedrooms
  • 2 bathrooms
  • sleeps 11

1 of 2 match: Secure parking, Rental types

1 of 2 filters match

Price per night from

$343

Fayston Barn

Waitsfield house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 12

1 of 2 match: Secure parking, Rental types

1 of 2 filters match

Price per night from

$1,030

Viewing 38 of 218
rentals in Pittsfield

×

Also consider