Pittsfield Private Home Rentals

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Check prices for these dates

Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov

Featured Private Holiday Homes in Pittsfield

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

Colony Club C12

3.5 star property
Colony Club C12
Hemlock Ridge 1D
Private kitchen

Hemlock Ridge 1D

3.5 star property
Hemlock Ridge 1D
Viewmont Chalet
Living area

Viewmont Chalet

3.5 star property
Viewmont Chalet
Breakaway House by Killington Vacation Rentals
Private kitchen

Breakaway House by Killington Vacation Rentals

2.0 star property
The price is S$738
includes taxes & fees
1 Oct - 2 Oct
Breakaway House by Killington Vacation Rentals
Pond View Cabin
Property grounds

Pond View Cabin

3.0 star property
Pond View Cabin
Forest Mountain Escape: Beautiful Mountaintop Escape In Mendon, Vt. 20 Min To Killington/14 To Pico. 4 Bedroom Home
Dining

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
Serene Architect-designed Vermont Chalet 4 Bedroom Home
Terrace/patio

Serene Architect-designed Vermont Chalet 4 Bedroom Home

3.5 star property
Serene Architect-designed Vermont Chalet 4 Bedroom Home
Great Escape Ski Lodge
Private kitchen

Great Escape Ski Lodge

3.0 star property
Great Escape Ski Lodge
Silver Spring Chalet Brought to you by GetAway Vacations
Living area

Silver Spring Chalet Brought to you by GetAway Vacations

2.5 star property
Silver Spring Chalet Brought to you by GetAway Vacations
Killington A-frame 2 Bedroom Home
Private kitchen

Killington A-frame 2 Bedroom Home

3.0 star property
The price is S$668
includes taxes & fees
26 Oct - 27 Oct
Killington A-frame 2 Bedroom Home
Rutland's Hidden Gem: 2 Br/1ba Renovated Home Close To Everything 2 Bedroom Home
Private kitchen

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

3.5 star property
The price is S$720
includes taxes & fees
5 Oct - 6 Oct
Rutland's Hidden Gem: 2 Br/1ba Renovated Home Close To Everything 2 Bedroom Home
Sweet Life - GetAway
In-room dining

Sweet Life - GetAway

3.5 star property
Sweet Life - GetAway
Mountainview Escape 4 Bedroom Home
Exterior

Mountainview Escape 4 Bedroom Home

2.0 star property
Mountainview Escape 4 Bedroom Home
Old Orchard House
Exterior

Old Orchard House

3.0 star property
Old Orchard House
The Waffelhaus In Killington 4 Bedroom Home
Private kitchen

The Waffelhaus In Killington 4 Bedroom Home

2.0 star property
The Waffelhaus In Killington 4 Bedroom Home
Tanglewood Chalet: 4 Br/4 Ba Family Home In Killington, Perfect For Groups 4 Bedroom Home
Exterior

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

2.0 star property
Tanglewood Chalet: 4 Br/4 Ba Family Home In Killington, Perfect For Groups 4 Bedroom Home
Shreadquarters 3 Bedroom Home
Exterior

Shreadquarters 3 Bedroom Home

2.0 star property
Shreadquarters 3 Bedroom Home
Alpine Court Chalet 4 Bedroom Home
Interior

Alpine Court Chalet 4 Bedroom Home

3.0 star property
Alpine Court Chalet 4 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

Brandon Inn

Brandon Inn

10/10 Excellent
"Very lovely gem that has become a new favorite! Fun to live like previous generations!!!"
Elizabeth 1-night trip
Posted 4 days ago
Brandon Inn

Find out more about Pittsfield

Find out more about Pittsfield

Pittsfield Private Holiday Homes information

Number of reviews
2
Accommodation
93 Private Holiday Homes
Lowest Price
S$668
Highest Price
S$738

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