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Pittsfield Rentals

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122 Results

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122 Houses

Killington area ski house

Pittsfield house

5 bedrooms / 2 bathrooms / sleeps 11

Price per night from

$432

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

Pittsfield house

4 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 2 hours 17 minutes

Price per night from

$231

Sweet Life

Pittsfield house

3 bedrooms / 2 bathrooms / sleeps 12

Responds fast! avg. 3 hours 31 minutes

Price per night from

$339

Silver Spring Chalet

Pittsfield house

4 bedrooms / 3 bathrooms / sleeps 11

Responds fast! avg. 3 hours 31 minutes

Price per night from

$339

Escape

Pittsfield house

4 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 3 hours 31 minutes

Price per night from

$487

Mountain Time

Pittsfield house

3 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 3 hours 31 minutes

Price per night from

$391

Great rentals within 20 miles that match your search

☆ 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. 12 minutes

Price per night from

$197

RV/Camper rental Randolph VT area

Braintree camper van

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$164

Organic Farm, House, Barn Event Rental

Hancock farmhouse

10 bedrooms / 4 bathrooms / sleeps 20

Price per night from

$1,245

Ski Killington Vermont

Killington apartment

1 bedroom / 2 bathrooms / sleeps 6

Price per night from

$249

Vermont Living Central Location

Rutland apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$328

Hidden House Vermont : Private Mountain Retreat in the Heart of The Green Mts.

Bethel apartment

3 bedrooms / 1 bathroom / sleeps 4

Price per night from

$302

Modern Country in Vermont

Rutland apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$230

ROSE'S COZY MOUNTAINVIEW - A -

Rutland townhouse

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$225

HOMESHARE at ROSE'S COZY MOUNTAINVIEW Duplex

Rutland house

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$70

Contemporary Spacious 7br/6.5 bath home near Killington VT

Mendon house

7 bedrooms / 7 bathrooms / sleeps 22

Price per night from

$975

Heavenly Vacation Home on Silver Lake

Barnard house

5 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$610

Cozy Apt Near Killington Ski Area & Sugarbush Farm

Bridgewater apartment

3 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 20 minutes

Price per night from

$190

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

Killington house

8 bedrooms / 6 bathrooms / sleeps 24

Responds fast! avg. 1 hour 56 minutes

Price per night from

$1,189

Plymouth Home w/ Jacuzzi Near Okemo & Killington!

Plymouth house

5 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 15 minutes

Price per night from

$451

ROSE'S COZY MOUNTAINVIEW -A & -B-

Mendon house

4 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$585

Serene & Private 20acre Mountain Getaway!

Bethel house

3 bedrooms / 3 bathrooms / sleeps 21

Price per night from

$698

INDESCRIBALE Mountain View Getaway! Tons of Amenities!

Shrewsbury house

4 bedrooms / 3 bathrooms / sleeps 20

Price per night from

$756

Killington Vermont- 2 Bedroom/1Bath. Right in the heart of Ski country!

Killington house

2 bedrooms / 1 bathroom / sleeps 8

Price per night from

$290

Ski House Between Killington and Okemo

Plymouth condo

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 13 minutes

Price per night from

$258

Sun House Studios

Sharon house

3 bedrooms / 2 bathrooms / sleeps 6

“Above expectations and perfect location for visiting Vermont Law School.” Perfect location for visiting Vermont Law School. Comfortable and all amenities that would be needed are provided. Clean and great attention to detail. Would return now that my Granddaughter will be attending VLS starting in the Fall.

Responds fast! avg. 2 hours 14 minutes

Price per night from

$171

The Little House Vermont

Brandon cottage

1 bedroom / 2 bathrooms / sleeps 4

Price per night from

$172

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

Brandon house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$246

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

$515

Premier Ski-in / Ski-out - 3 Bed, Sunrise Mountain

Killington apartment

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$746

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. 1 hour 33 minutes

Price per night from

$983

2 bedroom premium AAA rated condo across from the slopes-2D2

Killington condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 21 minutes

Price per night from

$226

ROSE'S COZY MOUNTAINVIEW - B -

Rutland house

2 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$184

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

Killington house

6 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$637

2 bedroom premium AAA rated condo across from the slopes-2C4

Killington condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 21 minutes

Price per night from

$226

Ski right home! Updated 1br condo, fireplace, pool, hot tub, fitness center.

Killington condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$291

Cozy country cabins with all the comforts of home!

South Royalton log cabin

2 bedrooms / 1 bathroom / sleeps 3

“A great cozy get away!” My boyfriend and I stayed at the upper cabin last week and it was just what we needed to relax. The cabin is beautifully decorated to make you feel right at home. The gas fire place in the living room really makes the cabin toasty. My favorite part is the view right out your window. The mountains are in the distance and you feel like you are miles away from civilization yet, the town of South Royalton is a mile and a half away. This vacation was the perfect mix of seclusion with the conveniences of pure luxury. Thanks Keith and Lisa for creating such a peaceful haven for us city dwellers! Casey from Baltimore, MD

Price per night from

$221

Suites at killington Center

Killington condo

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$349

Viewing 38 of 122
rentals in Pittsfield

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Top Destination reviews

Killington area mountain home on 60 acres and surrounded by National Forests
Green Mountain charm at its best

My family and I have stayed here a few times and absolutely love it. The house is rustic but beautifully maintained, and since it is the last house on the road, very few cars pass by. It's convenient to the ski slopes, there are a number of places to hike -- some challenging and others quite easy -- and there is a charming country store with a small restaurant and well-stocked wine cellar just a couple of miles away. Best of all, it's owned by family members who truly care about the property and want their renters to be comfortable and happy. We highly recommend it and can't wait to go back.see more
Killington area ski house
Great Place to stay with family

All rooms are very comfortable for a big family. House is a brand new and all equipment is new. Highly recommended! … see more

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