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In two weeks
Sep 5 - Sep 7
In two months
Oct 17 - Oct 19
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Nov 14 - Nov 16
In four months
Dec 12 - Dec 14

Vacation Homes in Pittsfield

Sunrise Mountain Village by RedAwning
Townhome, 4 Bedrooms | In-room dining

Sunrise Mountain Village by RedAwning

2.5 star property
Sunrise Mountain Village by RedAwning
The Queens Croft V2 - Luxury Killington Ski Home. Newer. Better. Ski-ier. 3 Bedroom Home
House, 3 Bedrooms | Living area

The Queens Croft V2 - Luxury Killington Ski Home. Newer. Better. Ski-ier. 3 Bedroom Home

3.0 star property
The Queens Croft V2 - Luxury Killington Ski Home. Newer. Better. Ski-ier. 3 Bedroom Home
The Green House: Killington's Most Unique Ski Home 4 Bedroom Home
House, 2 Bedrooms | Property grounds

The Green House: Killington's Most Unique Ski Home 4 Bedroom Home

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a great experience! Loved the unique decoration. Super close to the mountain for skiing and easy to walk to a restaurant down the road for dinner. "
The Green House: Killington's Most Unique Ski Home 4 Bedroom Home
Colony Club C12
Apartment, Multiple Beds (Colony Club C12) | Interior

Colony Club C12

3.5 star property
Colony Club C12
Viewmont Chalet
House, Multiple Beds (Viewmont Chalet) | Living area

Viewmont Chalet

3.5 star property
Viewmont Chalet
Hemlock Ridge 1D
House, Multiple Beds (Hemlock Ridge 1D) | Private kitchen | Fridge, microwave, stovetop, dishwasher

Hemlock Ridge 1D

3.5 star property
Hemlock Ridge 1D
Breakaway House by Killington Vacation Rentals
House, 3 Bedrooms | Living area

Breakaway House by Killington Vacation Rentals

2.0 star property
Breakaway House by Killington Vacation Rentals
Pond View Cabin
House, 1 Double Bed (Pond View Cabin) | Property grounds

Pond View Cabin

3.0 star property
Pond View Cabin
Serene Architect-designed Vermont Chalet 4 Bedroom Home
House, 4 Bedrooms | Terrace/patio

Serene Architect-designed Vermont Chalet 4 Bedroom Home

3.5 star property
Serene Architect-designed Vermont Chalet 4 Bedroom Home
Rutland's Hidden Gem: 2 Br/1ba Renovated Home Close To Everything 2 Bedroom Home
House, 2 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker

Rutland's Hidden Gem: 2 Br/1ba Renovated Home Close To Everything 2 Bedroom Home

3.5 star property
Rutland's Hidden Gem: 2 Br/1ba Renovated Home Close To Everything 2 Bedroom Home
Old Orchard House
House, Multiple Beds (Old Orchard House) | Exterior

Old Orchard House

3.0 star property
Old Orchard House
Bob's Sled Lodge 2 Bedroom Home
House, 2 Bedrooms | Exterior

Bob's Sled Lodge 2 Bedroom Home

3.0 star property
Bob's Sled Lodge 2 Bedroom Home
Dean Hill Chalet
House, Multiple Beds (Dean Hill Chalet) | Outdoor dining

Dean Hill Chalet

3.0 star property
Dean Hill Chalet
Great Escape Ski Lodge
House, Multiple Beds (Great Escape Ski Lodge) | Private kitchen | Oven, toaster

Great Escape Ski Lodge

3.0 star property
Great Escape Ski Lodge
Sugar Hollow 4 Bedroom Home
House, 4 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker

Sugar Hollow 4 Bedroom Home

3.0 star property
Sugar Hollow 4 Bedroom Home
The Waffelhaus In Killington 4 Bedroom Home
House, 4 Bedrooms | Private kitchen

The Waffelhaus In Killington 4 Bedroom Home

2.0 star property
The Waffelhaus In Killington 4 Bedroom Home
Beechwood Home Brought to you by GetAway Vacations
House, 4 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker, toaster

Beechwood Home Brought to you by GetAway Vacations

3.0 star property
Beechwood Home Brought to you by GetAway Vacations
Forest Mountain Escape: Beautiful Mountaintop Escape In Mendon, Vt. 20 Min To Killington/14 To Pico. 4 Bedroom Home
House, 4 Bedrooms | Property grounds

Forest Mountain Escape: Beautiful Mountaintop Escape In Mendon, Vt. 20 Min To Killington/14 To Pico. 4 Bedroom Home

3.0 star property
Forest Mountain Escape: Beautiful Mountaintop Escape In Mendon, Vt. 20 Min To Killington/14 To Pico. 4 Bedroom Home
Mountainview Escape 4 Bedroom Home
House, 4 Bedrooms | Exterior

Mountainview Escape 4 Bedroom Home

2.0 star property
Mountainview Escape 4 Bedroom Home
Old Orchard House Brought to you by GetAway Vacations
House, 5 Bedrooms | Property grounds

Old Orchard House Brought to you by GetAway Vacations

3.0 star property
Old Orchard House Brought to you by GetAway Vacations
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Pittsfield Hotel Reviews

The Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent
"The hotel is very nice, very friendly, beautiful views specially from the room with balcony. Game room is awesome and the breakfast was delicious. Will come back again. "
DANIEL 2-night trip
Posted 17 hours ago
The Mountain Inn at Killington