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Pittsfield Rentals

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age 0-16
97 Results

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Price: high to low

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97 Houses

Killington area mountain home on 60 acres and surrounded by National Forests

Pittsfield house

4 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$231

Sweet Life

Pittsfield house

3 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$322

Silver Spring Chalet

Pittsfield house

4 bedrooms / 3 bathrooms / sleeps 11

Price per night from

$331

Hawk Landing

Pittsfield house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$296

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

Price per night from

$248

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. 2 hours 15 minutes

Price per night from

$979

Ski Killington Vermont

Killington apartment

1 bedroom / 2 bathrooms / sleeps 6

Price per night from

$219

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

Killington house

6 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$634

Pico Resort Slopeside Condo, Killington Vermont

Killington condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$518

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

Killington house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$518

Price per night from

$575

RV/Camper rental Randolph VT area

Braintree camper van

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$144

Hideaway Chalet Comfort for 24 SKI PASSES 50% ski slopes 2min HOT TUB

Killington house

8 bedrooms / 6 bathrooms / sleeps 24

Price per night from

$1,382

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

Killington condo

2 bedrooms / 2 bathrooms / sleeps 6

“First Family Ski Trip with the Kids” I have a 4 year old and an 11 month old and neither my wife nor I had been skiing since both kids were born. Our eldest was ready for his first skiing vacation and Killington was a great spot since they have a great ski school and child care for the little one. We booked somewhat late but had another couple that wanted to bring their 4 year old daughter as well, so we found this awesome rental. Unfortunately we didn't really get to use the ski on/off to its fullest potential since we had to drop the kids off at their base each day but it would have been extremely convenient. The condo was the perfect size, wifi was key along with the other amenities. The clubhouse was close and convenient, awesome to be able to take the kids to the pool after a day on the slopes and sit myself in the hot tub while they played. I will definitely be coming back here!

Responds fast! avg. 1 hour 36 minutes

Price per night from

$173

Farmhouse Rustic Lux on 10 acres w/ swimming pond

Bridgewater house

7 bedrooms / 4 bathrooms / sleeps 22

Responds fast! avg. 2 hours 14 minutes

Price per night from

$749

Ski House Between Killington and Okemo

Plymouth condo

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 14 minutes

Price per night from

$259

INDESCRIBALE Mountain View Getaway! Tons of Amenities!

Shrewsbury house

4 bedrooms / 3 bathrooms / sleeps 20

Price per night from

$805

Serene & Private 20acre Mountain Getaway!

Bethel house

3 bedrooms / 3 bathrooms / sleeps 21

Price per night from

$575

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

Barnard house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$398

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

Killington house

5 bedrooms / 3 bathrooms / sleeps 14

Price per night from

$778

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

Killington condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$259

Killington Mountain Home HotTub & 5 min to Skiing

Killington house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 12 minutes

Price per night from

$279

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

Price per night from

$491

Suites at killington Center

Killington condo

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$346

The "76" House, A VERMONT HOME WITH AC!

Killington house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 11 minutes

Price per night from

$1,106

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

Killington house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 2 hours 11 minutes

Price per night from

$956

Luxury One Bedroom Condominium #7 SkiOnSkiOff Great Eastern Ski Trail!

Killington apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 11 minutes

Price per night from

$453

Luxury Trailside Village 3 Bedroom #8 SkiOnSkiOff Great Eastern Ski Trail!

Killington apartment

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 11 minutes

Price per night from

$553

Luxury Trailside Village Three Bedroom #6 SkiOnSkiOff Great Eastern Ski Trai!

Killington apartment

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 11 minutes

Price per night from

$553

Luxury Topridge Unit 17B off Bear Mountain in Killington.

Killington house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 2 hours 11 minutes

Price per night from

$956

VERMONT SKI/SUMMER HOME WITH AC - The Matterhorn House

Killington house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 11 minutes

Price per night from

$1,398

Trailside Village One Bedroom Condominium #5

Killington condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 11 minutes

Price per night from

$453

LUXURY 5 Bedrooms-6.5 Bath The Mountainside House - SKi-OFF in Killington!

Killington house

6 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 2 hours 11 minutes

Price per night from

$2,011

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

Killington apartment

1 bedroom / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 11 minutes

Price per night from

$553

Luxury Slopeside Estate Ski-On/Ski-Off on the Great Eastern Ski Trail!

Killington house

5 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 2 hours 11 minutes

Price per night from

$2,011

Luxury One Bedroom Condominium #3 SkiOnSkiOff Great Eastern Ski Trail!

Killington condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 11 minutes

Price per night from

$453

Luxury Trailside Village Three Bedroom #4 SkiOnSkiOff Great Eastern Ski Trail

Killington condo

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 11 minutes

Price per night from

$553

LUXURY Ski-On/Ski-Off - The Navillus House on the Great Eastern Ski Trail!

Killington house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 11 minutes

Price per night from

$1,237

Viewing 38 of 97
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