Search Private Holiday Homes in Pittsfield

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec

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
Sunrise Mountain Village by RedAwning
In-room dining

Sunrise Mountain Village by RedAwning

2.0 star property
Sunrise Mountain Village by RedAwning
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 RM861
RM2,505 total
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 RM1,157
RM2,186 total
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 RM1,209
RM2,498 total
includes taxes & fees
5 Oct - 6 Oct
Rutland's Hidden Gem: 2 Br/1ba Renovated Home Close To Everything 2 Bedroom Home
Sugar Hollow 4 Bedroom Home
Private kitchen

Sugar Hollow 4 Bedroom Home

3.0 star property
Sugar Hollow 4 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
Beechwood Home Brought to you by GetAway Vacations
Private kitchen

Beechwood Home Brought to you by GetAway Vacations

3.0 star property
Beechwood Home Brought to you by GetAway Vacations
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
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pittsfield Hotel Reviews

North Star Lodge and Resort

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 1 day ago
North Star Lodge and Resort

Find out more about Pittsfield

Find out more about Pittsfield

Pittsfield Private Holiday Homes information

Number of reviews
2
Accommodation
92 Private Holiday Homes
Lowest Price
RM2,186
Highest Price
RM2,505

Explore a world of travel with Expedia

Explore a world of travel with Expedia