Vacation Rentals & House Rentals in Pittsfield

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Wireless Internet
Swimming pool
Private pool
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Jacuzzi or hot tub
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Cot available
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Housekeeping Included

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Pets
Pets allowed
Parking
Car not required

Children under 5
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Non-Smoking property
Smoking - Ask
Elevator access
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Beach or lakeside relaxation
City breaks
Skiing – property near ski resort
Walking trips

Tennis in town
Nightlife
Water sports
Horse riding
Fishing
Cycling trips
Golf course on site or within 15 min walk
Mountain Views
Beach or lakeside relaxation
Golf within 30mins drive
Lakefront
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31 Houses

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Sweet Life

Pittsfield house

3 bedrooms
2 bathrooms

sleeps 8

Match: Kettle

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Price per night from

$367

Great rentals within 20 miles that match your search

The Farmhouse Condo at Killington: Renovated Luxury Condo Close to Everything!

Killington condo

1 bedroom
2 bathrooms

sleeps 6

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Price per night from

$189

River Stone Lodge MTN Views, River, Hiking, Hot Tub, WIFI, Campfires, 4 bedrooms

Ripton house

5 bedrooms
3 bathrooms

sleeps 8

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Price per night from

$571

RV/Camper rental Randolph VT area

Braintree camper van

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$143

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

Killington house

4 bedrooms
2 bathrooms

sleeps 8

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Price per night from

$858

INDESCRIBALE Mountain View Getaway! Tons of Amenities!

Shrewsbury house

4 bedrooms
3 bathrooms

sleeps 20

Responds fast! avg. 37 minutes

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Price per night from

$457

Red Acre Cottage in the Green Mountains of Vermont

Hancock house

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$143

Contemporary Spacious 7br/6.5 bath home near Killington VT

Mendon house

7 bedrooms
7 bathrooms

sleeps 22

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Price per night from

$914

NEW! Luxe Lodge with Best Views, near Silver Lake+Woodstock

Barnard house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$395

Pico Slopeside I 102

Killington condo

3 bedrooms
2 bathrooms

sleeps 8

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Price per night from

$323

Sunrise Timberline A2 - Ski Shack

Killington condo

3 bedrooms
3 bathrooms

sleeps 8

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Price per night from

$382

Pico Village Resort D209

Killington condo

1 bedroom
1 bathroom

sleeps 4

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Price per night from

$164

Pico Village Resort G301

Killington condo

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$211

Mt Green 2-F04

Killington house

2 bedrooms
1 bathroom

sleeps 6

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Price per night from

$205

Woods Village 10

Killington house

1 bedroom
2 bathrooms

sleeps 4

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Price per night from

$172

Gateway Condominium Unit 25

Mendon condo

2 bedrooms
1 bathroom

sleeps 4

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Price per night from

$149

Beechwood

Mendon house

4 bedrooms
3 bathrooms

sleeps 10

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Price per night from

$323

Pico Village Resort H304

Killington house

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$225

Mt Green 1-B01

Killington condo

2 bedrooms
1 bathroom

sleeps 6

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Price per night from

$231

The Mendon House

Killington house

3 bedrooms
3 bathrooms

sleeps 9

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Price per night from

$286

Killington- 6 Bedroom, 3 Bath. Right in the heart of Ski country!

Killington house

6 bedrooms
3 bathrooms

sleeps 10

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Price per night from

$1,088

Suites at Killington: Luxury 2 BR Resort Ski Condo

Killington condo

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$166

Mt Green 3-D10

Killington house

4 bedrooms
3 bathrooms

sleeps 10

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Price per night from

$373

Killington - FALL IN THE MOUNTAINS...YOU CAN'T BEAT THE VIEWS!

Killington condo

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$258

Spectacular Water Views From Every Room ~ Directly On Lake Hortonia, Vt.

Brandon house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$247

Hakuna Matata

Bridgewater house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$371

Ski Killington Vermont

Killington apartment

1 bedroom
2 bathrooms

sleeps 6

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Price per night from

$218

Mt Green 2-F09

Killington studio

Studio
1 bathroom

sleeps 4

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Price per night from

$163

Mt Green 2-F06

Killington house

1 bedroom
1 bathroom

sleeps 4

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Price per night from

$177

Mt Green 2-D01

Killington house

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$220

Mt Green 2-C03

Killington house

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$258

Also consider

Stowe 165 properties
Killington 64 properties
Ludlow 16 properties
Northeast Kingdom 14 properties
Mendon 7 properties
Northfield 7 properties
Jeffersonville 7 properties
Wallingford 6 properties
Morrisville 5 properties
Underhill Center 5 properties
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Pittsfield Rentals

Per night

31 Houses

Sweet Life

The Farmhouse Condo at Killington: Renovated Luxury Condo Close to Everything!

River Stone Lodge MTN Views, River, Hiking, Hot Tub, WIFI, Campfires, 4 bedrooms

RV/Camper rental Randolph VT area

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

INDESCRIBALE Mountain View Getaway! Tons of Amenities!

Red Acre Cottage in the Green Mountains of Vermont

Contemporary Spacious 7br/6.5 bath home near Killington VT

NEW! Luxe Lodge with Best Views, near Silver Lake+Woodstock

Pico Slopeside I 102

Sunrise Timberline A2 - Ski Shack

Pico Village Resort D209

Pico Village Resort G301

Mt Green 2-F04

Woods Village 10

Gateway Condominium Unit 25

Beechwood

Pico Village Resort H304

Mt Green 1-B01

The Mendon House

Killington- 6 Bedroom, 3 Bath. Right in the heart of Ski country!

Suites at Killington: Luxury 2 BR Resort Ski Condo

Mt Green 3-D10

Killington - FALL IN THE MOUNTAINS...YOU CAN'T BEAT THE VIEWS!

Spectacular Water Views From Every Room ~ Directly On Lake Hortonia, Vt.

Hakuna Matata

Ski Killington Vermont

Mt Green 2-F09

Mt Green 2-F06

Mt Green 2-D01

Mt Green 2-C03

Viewing 31 of 31
rentals in Pittsfield

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Pittsfield Rentals

Per night

31 Houses

Viewing 31 of 31rentals in Pittsfield

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Viewing 31 of 31
rentals in Pittsfield