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Fireplace
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Cot available
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City breaks
Skiing – property near ski resort
Walking trips
Tennis in town

Nightlife
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Golf course on site or within 15 min walk
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Beach or lakeside relaxation
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69 Houses

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Sweet Life

Pittsfield house

3 bedrooms
2 bathrooms

sleeps 8

Match: Fireplace

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Price per night from

$410

Wintergreen 106

Pittsfield condo

1 bedroom
1 bathroom

sleeps 4

Match: Fireplace

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Price per night from

$172

Hawk Landing

Pittsfield house

3 bedrooms
2 bathrooms

sleeps 6

Match: Fireplace

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Price per night from

$387

Great rentals within 20 miles that match your search

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

Brandon house

3 bedrooms
2 bathrooms

sleeps 6

Match: Fireplace

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Price per night from

$247

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!

Match: Fireplace

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Price per night from

$974

Ski Killington Vermont

Killington apartment

1 bedroom
2 bathrooms

sleeps 6

Match: Fireplace

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Price per night from

$218

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

Killington house

6 bedrooms
3 bathrooms

sleeps 10

Match: Fireplace

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Price per night from

$1,088

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

Ripton house

5 bedrooms
3 bathrooms

sleeps 8

Match: Fireplace

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Price per night from

$572

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

Killington house

4 bedrooms
2 bathrooms

sleeps 8

Match: Fireplace

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Price per night from

$859

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

Killington condo

1 bedroom
2 bathrooms

sleeps 6

Match: Fireplace

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Price per night from

$189

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

Historic, freshly renovated 2 family home on bus route to Ski Resorts!!

Rutland house

2 bedrooms
1 bathroom

sleeps 5

Match: Fireplace

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Price per night from

$344

Historic, freshly renovated 2 family home on bus route to Ski Resorts!!

Rutland house

2 bedrooms
1 bathroom

sleeps 5

Match: Fireplace

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Price per night from

$344

Breakaway House - Unit A & B

Killington house

6 bedrooms
4 bathrooms

sleeps 16

Match: Fireplace

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Price per night from

$667

6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 9-10, Pet Friendly, Views, Grill

Chittenden house

4 bedrooms
2 bathrooms

sleeps 10

Match: Fireplace

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Price per night from

$687

KILLINGTON GOLFING, BIKING SKI 2 Bd 1&1/2 B $79 av nt. 4 Season Resort Sleeps 6

Killington condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Fireplace

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Price per night from

$488

Killington/Rutlan 2 Bedroom w/NO Hidden Fees

Mendon house

2 bedrooms
1 bathroom

sleeps 6

Match: Fireplace

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Price per night from

$217

LUXURY, hot tub, private, 6 BR, 3 BA

Killington house

5 bedrooms
3 bathrooms

sleeps 14

Match: Fireplace

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Price per night from

$1,260

Clean/Comfortable 2 Bdroom Cabin w/No Hidden Fees*

Mendon house

2 bedrooms
3 bathrooms

sleeps 6

Match: Fireplace

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Price per night from

$205

Clean/Comfortable 1 Bdrm Cabin w/NO Hidden Fees*

Killington house

1 bedroom
1 bathroom

sleeps 4

Match: Fireplace

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Price per night from

$194

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

Barnard house

3 bedrooms
2 bathrooms

sleeps 6

Match: Fireplace

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Price per night from

$395

Red Acre Cottage in the Green Mountains of Vermont

Hancock house

2 bedrooms
2 bathrooms

sleeps 6

Match: Fireplace

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Price per night from

$144

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

Killington condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Fireplace

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Price per night from

$258

Contemporary Spacious 7br/6.5 bath home near Killington VT

Mendon house

7 bedrooms
7 bathrooms

sleeps 22

Match: Fireplace

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Price per night from

$916

☆ SKI ON & OFF! ☆ Luxury Trailside Townhome! NEW Steam Shower, Hot Tub, Pool

Killington townhouse

3 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 8 minutes

Match: Fireplace

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Price per night from

$126

☆ SKI ON & OFF! ☆ Spruce Glen B on Great Eastern Trail w/Sauna+Fireplace

Killington townhouse

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 8 minutes

Match: Fireplace

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Price per night from

$87

☆ SKI ON & OFF! ☆ Spruce Glen C on Great Eastern Trail w/Sauna, Fireplace

Killington townhouse

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 8 minutes

Match: Fireplace

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Price per night from

$93

☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/Sauna, Fireplace

Killington townhouse

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 8 minutes

Match: Fireplace

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Price per night from

$93

☆ SKI ON & OFF! ☆ Spruce Glen A on Great Eastern Trail w/Sauna, Fireplace

Killington townhouse

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 8 minutes

Match: Fireplace

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Price per night from

$89

Walk to lift, Ski home! Closest unit to Lifts, Sports Center & Ski Home trail!

Killington condo

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 8 minutes

Match: Fireplace

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Price per night from

$131

Pico Slopeside I 102

Killington condo

3 bedrooms
2 bathrooms

sleeps 8

Match: Fireplace

All filters match

Price per night from

$323

Woods Village 43

Killington condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Fireplace

All filters match

Price per night from

$269

Pond View Cabin

Chittenden log cabin

2 bedrooms
1 bathroom

sleeps 4

Match: Fireplace

All filters match

Price per night from

$148

Pico Village Resort H304

Killington house

2 bedrooms
2 bathrooms

sleeps 6

Match: Fireplace

All filters match

Price per night from

$215

Pico Village Resort G301

Killington condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Fireplace

All filters match

Price per night from

$211

Pico Village Resort D209

Killington condo

1 bedroom
1 bathroom

sleeps 4

Match: Fireplace

All filters match

Price per night from

$164

Sunrise - W Glade K-5

Killington condo

3 bedrooms
2 bathrooms

sleeps 8

Match: Fireplace

All filters match

Price per night from

$306

Sunrise Timberline A2 - Ski Shack

Killington condo

3 bedrooms
3 bathrooms

sleeps 8

Match: Fireplace

All filters match

Price per night from

$379

Viewing 38 of 69
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Pittsfield Rentals

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69 Houses

Viewing 38 of 69rentals in Pittsfield

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Viewing 38 of 69
rentals in Pittsfield