Pittsfield Vacation Homes
Vermont
United States of America
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Vacation Homes in Pittsfield

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

3.0 star property

Killington

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

Condo, 3 Bedrooms | Private kitchen | Fridge, coffee/tea maker, toaster

Townhome, 3 Bedrooms | Living area | Smart TV

Sunrise Mountain Village by RedAwning

2.0 star property

Killington

Sunrise Mountain Village by RedAwning

House, 2 Bedrooms | 2 bedrooms, free WiFi

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

2.0 star property

Killington

10.0 out of 10, Exceptional, (2)

10/10

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

Apartment, Multiple Beds (Colony Club C12) | Interior

Colony Club C12

3.5 star property

Killington

Colony Club C12

House, Multiple Beds (Hemlock Ridge 1D) | Private kitchen | Fridge, microwave, stovetop, dishwasher

House, Multiple Beds (Hemlock Ridge 1D) | Dining

Hemlock Ridge 1D

3.5 star property

Killington

Hemlock Ridge 1D

House, Multiple Beds (Viewmont Chalet) | Living area

House, Multiple Beds (Viewmont Chalet) | Private kitchen

Viewmont Chalet

3.5 star property

Killington

Viewmont Chalet

Breakaway House by Killington Vacation Rentals

2.0 star property

Killington

Breakaway House by Killington Vacation Rentals

House, 1 Double Bed (Pond View Cabin) | Property grounds

Pond View Cabin

3.0 star property

Rutland

Pond View Cabin

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

3.0 star property

Rutland

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

House, 4 Bedrooms | Living area | Smart TV, streaming services

House, 4 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker, toaster

Serene Architect-designed Vermont Chalet 4 Bedroom Home

3.5 star property

Pittsfield

Serene Architect-designed Vermont Chalet 4 Bedroom Home

House, Multiple Beds (Great Escape Ski Lodge) | Private kitchen | Oven, toaster

House, Multiple Beds (Great Escape Ski Lodge) | Living area

Great Escape Ski Lodge

3.0 star property

Killington

Great Escape Ski Lodge

House, 2 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker, toaster

Killington A-frame 2 Bedroom Home

3.0 star property

North Sherburne

The price is NT$8,341

NT$8,341

NT$15,767 total

includes taxes & fees

Oct 26 - Oct 27

Killington A-frame 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

The price is NT$8,382

NT$8,382

NT$17,575 total

includes taxes & fees

Oct 5 - Oct 6

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

House, 4 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker

House, 4 Bedrooms | Living area | Smart TV

Sugar Hollow 4 Bedroom Home

3.0 star property

Rutland

Sugar Hollow 4 Bedroom Home

House, Multiple Beds, Mountain View (Sweet Life) | In-room dining

House, Multiple Beds, Mountain View (Sweet Life) | Bathroom | Combined shower/tub, spring water tub, free toiletries, hair dryer

House, Multiple Beds, Mountain View (Sweet Life) | Balcony

House, Multiple Beds, Mountain View (Sweet Life) | Staircase

Sweet Life - GetAway

3.5 star property

Pittsfield

Sweet Life - GetAway

Mountainview Escape 4 Bedroom Home

2.0 star property

North Sherburne

Mountainview Escape 4 Bedroom Home

House, Multiple Beds (Old Orchard House) | Exterior

House, Multiple Beds (Old Orchard House) | 5 bedrooms

Old Orchard House

3.0 star property

Brandon

Old Orchard House

House, 4 Bedrooms | 4 bedrooms, free WiFi

The Waffelhaus In Killington 4 Bedroom Home

2.0 star property

Killington

The Waffelhaus In Killington 4 Bedroom Home

Tanglewood Chalet: 4 Br/4 Ba Family Home In Killington, Perfect For Groups 4 Bedroom Home

2.0 star property

Killington

Tanglewood Chalet: 4 Br/4 Ba Family Home In Killington, Perfect For Groups 4 Bedroom Home

Shreadquarters 3 Bedroom Home

2.0 star property

Killington

Shreadquarters 3 Bedroom Home

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

Mountain Sports Inn

10/10 Excellent

"Great "

Shu 1-night trip

Posted 1 day ago

Mountain Sports Inn

Best Western Inn & Suites Rutland-Killington

10/10 Excellent

"Our room was great! We got an upgrade and our room even had a patio! "

Julia 1-night trip

Posted 2 days ago

Best Western Inn & Suites Rutland-Killington

Comfort Inn Rutland - Killington

10/10 Excellent

"Great place to stay. Well kept."

Bianca 1-night trip

Posted 2 days ago

Comfort Inn Rutland - Killington

Cortina Inn

6/10 Okay

"This hotel appears to be in the middle of a renovation (9/26/25). Room was clean and comfortable. Hallways and outside need work. Very few amenities."

Stanley 1-night trip

Posted 2 days ago

Cortina Inn

Greenbrier Inn

10/10 Excellent

"Wonderful staff "

Patricia 1-night trip

Posted 2 days ago

Greenbrier Inn

Killington Mountain Lodge, Tapestry Collection by Hilton

10/10 Excellent

"Best place in Killington!"

Donald 1-night trip

Posted 2 days ago

Killington Mountain Lodge, Tapestry Collection by Hilton

North Star Lodge and Resort

10/10 Excellent

"Central location in Vermont! Best place I stay at up on Killington. Has fireplace with sitting area in lobby, game room, coffee in morning and a Heated Pool! The grounds are. Ice with picnic tables around pond! Located near everything in mountain!"

Beverly 3-night trip

Posted 3 days ago

North Star Lodge and Resort

Brandon Inn

10/10 Excellent

"Historic building very well maintained. Friendly and helpful staff. Great location in town "

Dave 1-night trip

Posted 4 days ago

Brandon Inn

Days Inn by Wyndham Rutland/Killington Area

10/10 Excellent

"The staff was fantastic the room was clean and they allowed me to bring my dog "

Edward 1-night trip

Posted 4 days ago

Days Inn by Wyndham Rutland/Killington Area

Find out more about Pittsfield

Pittsfield Vacation Homes information

Number of reviews	2
Accommodation	93 Vacation Homes
Lowest Price	NT$15,767
Highest Price	NT$17,575

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Search Vacation Homes in Pittsfield

Change your mind

Treat yourself

Be picky

Check prices for these dates

Vacation Homes in Pittsfield

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

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

Sunrise Mountain Village by RedAwning

Sunrise Mountain Village by RedAwning

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

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

Colony Club C12

Colony Club C12

Hemlock Ridge 1D

Hemlock Ridge 1D

Viewmont Chalet

Viewmont Chalet

Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals

Pond View Cabin

Pond View Cabin

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

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

Serene Architect-designed Vermont Chalet 4 Bedroom Home

Serene Architect-designed Vermont Chalet 4 Bedroom Home

Great Escape Ski Lodge

Great Escape Ski Lodge

Killington A-frame 2 Bedroom Home

Killington A-frame 2 Bedroom Home

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

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

Sugar Hollow 4 Bedroom Home

Sugar Hollow 4 Bedroom Home

Sweet Life - GetAway

Sweet Life - GetAway

Mountainview Escape 4 Bedroom Home

Mountainview Escape 4 Bedroom Home

Old Orchard House

Old Orchard House

The Waffelhaus In Killington 4 Bedroom Home

The Waffelhaus In Killington 4 Bedroom Home

Tanglewood Chalet: 4 Br/4 Ba Family Home In Killington, Perfect For Groups 4 Bedroom Home

Tanglewood Chalet: 4 Br/4 Ba Family Home In Killington, Perfect For Groups 4 Bedroom Home

Shreadquarters 3 Bedroom Home

Shreadquarters 3 Bedroom Home

Top Pittsfield Hotel Reviews

Mountain Sports Inn

Find out more about Pittsfield

Find out more about Pittsfield

Pittsfield Vacation Homes information

Explore a world of travel with Expedia

Explore a world of travel with Expedia

More Accommodation Types in Pittsfield

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