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Pittsfield Rentals

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age 0-16
209 Results

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Price: high to low

Number of reviews

209 Houses

Charming condo w/ shared hot tub - near golf, ski trails & fishing!

Pittsfield house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$99

Colonial home with a yard & deck, close to golf & skiing!

Pittsfield house

5 bedrooms / 3 bathrooms / sleeps 13

Price per night from

$205

Killington area ski house

Pittsfield house

5 bedrooms / 2 bathrooms / sleeps 11

Responds fast! avg. 3 hours 20 minutes

Price per night from

$434

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

Pittsfield house

4 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$172

Sweet Life

Pittsfield house

3 bedrooms / 2 bathrooms / sleeps 12

Responds fast! avg. 2 hours 54 minutes

Price per night from

$335

Dog-friendly cottage w/ deck & beautiful views - close to golf, skiing, & trail

Pittsfield house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$162

Escape

Pittsfield house

4 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 2 hours 54 minutes

Price per night from

$267

Silver Spring Chalet

Pittsfield house

4 bedrooms / 3 bathrooms / sleeps 11

Responds fast! avg. 2 hours 54 minutes

Price per night from

$227

Great rentals within 20 miles that match your search

Heavenly Vacation Home on Silver Lake

Barnard house

5 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$570

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

Killington house

6 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$634

Great Bear Lodge

Sharon house

5 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$403

Private Green Mountain get-away with pond

Ripton house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$231

Minutes from Killington + Okemo + Woodstock, VT come and experience The Cabin

Bridgewater log cabin

4 bedrooms / 3 bathrooms / sleeps 24

Price per night from

$924

☆ 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

$174

ROSE'S COZY MOUNTAINVIEW - A -

Rutland townhouse

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$207

Modern Farmhouse-Superb Meadow and MTN Views

Rochester house

3 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$693

Heavenly on Killington Access Road Brand New House

Killington house

7 bedrooms / 4 bathrooms / sleeps 16

Price per night from

$635

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

Killington house

8 bedrooms / 6 bathrooms / sleeps 24

Responds fast! avg. 3 hours 5 minutes

Price per night from

$1,018

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. 3 hours 8 minutes

Price per night from

$694

Colonial-style solid-timber home in a quiet setting; sanctuary.

Barnard house

3 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$278

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

Killington apartment

3 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$752

Ski Killington, Pico, Snow Mobile, Summer Fun

Killington house

5 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$579

Swiss Chalet 8-Bdrooms_6 F-Bathrooms X-Mass *Grps 5+

Killington chalet

8 bedrooms / 6 bathrooms / sleeps 22

Price per night from

$579

The Little House Vermont

Brandon cottage

1 bedroom / 2 bathrooms / sleeps 4

Price per night from

$173

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

Killington condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$226

KILLINGTON GOLFING, BIKING SKI 2 Bd 1&1/2 B $79 av nt. 4 Season Resort Sleeps 8

Killington condo

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 49 minutes

Price per night from

$111

RV/Camper rental Randolph VT area

Braintree camper van

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$145

The Lodges Bear Mountain Luxury ski-on/ski-off 3 bed 3 Bath LOW RATES-Mar/Apr

Killington condo

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$342

ROSE'S COZY MOUNTAINVIEW - B -

Rutland house

2 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$184

Price per night from

$521

Organic Farm, House, Barn Event Rental

Hancock farmhouse

10 bedrooms / 4 bathrooms / sleeps 20

Price per night from

$1,099

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

Killington house

5 bedrooms / 3 bathrooms / sleeps 16

Price per night from

$636

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

Responds fast! avg. 1 hour 45 minutes

Price per night from

$220

Killington Furnished Private Apartment

Killington apartment

2 bedrooms / 1 bathroom / sleeps 3

Price per night from

$174

Ski Killington Vermont

Killington apartment

1 bedroom / 2 bathrooms / sleeps 6

Price per night from

$220

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. 1 hour 51 minutes

Price per night from

$174

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

Killington house

2 bedrooms / 1 bathroom / sleeps 8

Price per night from

$289

Cricket Hill - Cozy, clean, private, spacious. 5 rooms. Entire lower level.

Killington house

3 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 4 minutes

Price per night from

$151

Viewing 38 of 209
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

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