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City breaks
Skiing – property near ski resort
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142 Houses

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

Pittsfield house

4 bedrooms
2 bathrooms

sleeps 9

Price per night from

$229

Sweet Life

Pittsfield house

3 bedrooms
2 bathrooms

sleeps 12

Price per night from

$248

Silver Spring Chalet

Pittsfield house

4 bedrooms
3 bathrooms

sleeps 11

Price per night from

$220

Wintergreen 106

Pittsfield condo

1 bedroom
1 bathroom

sleeps 4

Price per night from

$109

Hawk Landing

Pittsfield house

3 bedrooms
2 bathrooms

sleeps 6

Price per night from

$387

Great rentals within 20 miles that match your search

Farmhouse Rustic Lux on 10 acres w/ swimming pond

Bridgewater house

7 bedrooms
4 bathrooms

sleeps 22

Responds fast! avg. 1 hour 32 minutes

Price per night from

$747

INDESCRIBALE Mountain View Getaway! Tons of Amenities!

Shrewsbury house

4 bedrooms
3 bathrooms

sleeps 20

Price per night from

$689

Ski House Between Killington and Okemo

Plymouth condo

4 bedrooms
2 bathrooms

sleeps 8

Responds fast! avg. 14 minutes

Price per night from

$259

Double Dipper - Lower Level

Killington house

3 bedrooms
1 bathroom

sleeps 7

Responds fast! avg. 3 hours 50 minutes

Price per night from

$399

Hemlock Ridge 2B *

Killington condo

3 bedrooms
2 bathrooms

sleeps 8

Responds fast! avg. 3 hours 50 minutes

Price per night from

$172

Amazing Skiing! Fun In Fun Out Killington Ski Home - Upper Level. Renovated

Killington house

3 bedrooms
2 bathrooms

sleeps 8

Responds fast! avg. 3 hours 50 minutes

Price per night from

$332

FL E4

Sherburne condo

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 50 minutes

Price per night from

$199

Location! Location! 1BR/1BA Steps to Mountain. 3E3

Killington condo

1 bedroom
1 bathroom

sleeps 4

Responds fast! avg. 3 hours 50 minutes

Price per night from

$131

The Giguere House at Killington - Large Renovated 5BR/5.5BA Home Close to Mtn

Killington house

5 bedrooms
6 bathrooms

sleeps 14

Responds fast! avg. 3 hours 50 minutes

Price per night from

$599

Breakaway House - Unit A *

Killington house

3 bedrooms
2 bathrooms

sleeps 8

Responds fast! avg. 3 hours 50 minutes

Price per night from

$305

MG #3D6

Killington condo

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 50 minutes

Price per night from

$172

The Killington Chalet on Merrill - Large Ski Chalet Perfect for Groups. 8 BR

Killington chalet

6 bedrooms
5 bathrooms

sleeps 16

Responds fast! avg. 3 hours 50 minutes

Price per night from

$612

Fun In Fun Out Killington Ski Home. Hot tubs! Saunas! Groups! 6BR/4BA

Killington house

6 bedrooms
4 bathrooms

sleeps 16

Responds fast! avg. 3 hours 50 minutes

Price per night from

$863

KCIS #31

Killington condo

2 bedrooms
3 bathrooms

sleeps 6

Responds fast! avg. 3 hours 50 minutes

Price per night from

$236

Hot Tub, Renovated! Double Dipper Ski Home at Killington Mountain: Upper Level

Killington house

4 bedrooms
2 bathrooms

sleeps 10

Responds fast! avg. 3 hours 50 minutes

Price per night from

$666

MG #3F9

Killington studio

Studio
1 bathroom

sleeps 4

Responds fast! avg. 3 hours 50 minutes

Price per night from

$123

Woods V5

Killington condo

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 50 minutes

Price per night from

$224

Renovated! Double Dipper: Upper and Lower Level of Duplex Ski Home at Killington

Killington house

7 bedrooms
3 bathrooms

sleeps 16

Responds fast! avg. 3 hours 50 minutes

Price per night from

$998

The Grande Suite at Killington 331/2

Killington condo

2 bedrooms
3 bathrooms

sleeps 10

Responds fast! avg. 3 hours 50 minutes

Price per night from

$332

Cortina Mountain Chalet

Mendon house

3 bedrooms
3 bathrooms

sleeps 8

Responds fast! avg. 3 hours 50 minutes

Price per night from

$466

MG #1D6

Killington condo

1 bedroom
1 bathroom

sleeps 4

Responds fast! avg. 3 hours 50 minutes

Price per night from

$223

MG #2F8

Killington condo

1 bedroom
1 bathroom

sleeps 4

Responds fast! avg. 3 hours 50 minutes

Price per night from

$212

The Birch Ridge: Family Room #11 - Queen/Bunkbed Suite in Killington, Vermont

Killington house

1 bedroom
1 bathroom

sleeps 4

Responds fast! avg. 3 hours 50 minutes

Price per night from

$1,441

The Birch Ridge: English Gentleman's Room #9 - King Suite in Killington

Killington house

1 bedroom
1 bathroom

sleeps 2

Responds fast! avg. 3 hours 50 minutes

Price per night from

$1,218

The Birch Ridge: Mission Room #4 - Queen Suite in Killington, Vermont

Killington house

1 bedroom
1 bathroom

sleeps 2

Responds fast! avg. 3 hours 50 minutes

Price per night from

$1,198

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

Rutland house

2 bedrooms
1 bathroom

sleeps 5

Price per night from

$345

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

Rutland house

2 bedrooms
1 bathroom

sleeps 5

Price per night from

$345

Killington Mountain Home HotTub & 5 min to Skiing

Killington house

3 bedrooms
2 bathrooms

sleeps 8

Responds fast! avg. 3 hours 50 minutes

Price per night from

$198

Rutland's Hidden Gem: 2 BR/1BA Renovated Home Close to Everything

Rutland house

2 bedrooms
1 bathroom

sleeps 6

Responds fast! avg. 3 hours 50 minutes

Price per night from

$199

Left Duplex Home Directly Across From Pico Mountain, Close to Killington.

Killington house

3 bedrooms
2 bathrooms

sleeps 8

Responds fast! avg. 3 hours 50 minutes

Price per night from

$266

FL E2A

Killington condo

1 bedroom
1 bathroom

sleeps 2

Responds fast! avg. 3 hours 50 minutes

Price per night from

$120

Tanglewood Blues

Killington house

4 bedrooms
3 bathrooms

sleeps 8

Responds fast! avg. 3 hours 50 minutes

Price per night from

$299

Forest Suites: Sleep 10 in Killington Center Condo-hotel *******

Killington condo

2 bedrooms
3 bathrooms

sleeps 10

Responds fast! avg. 3 hours 50 minutes

Price per night from

$332

Viewing 38 of 142
rentals in Pittsfield

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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Pittsfield Rentals

Per night

142 Houses

Viewing 38 of 142rentals in Pittsfield

Top Destination reviews

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Viewing 38 of 142
rentals in Pittsfield