Search Vacation Homes in Pittsfield
Change your mind
Book hotels with free cancellation
Be picky
Search almost a million properties worldwide
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Compare 626 Vacation Homes in Pittsfield with updated reviews, rates, and availability.

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
9.8 out of 10, Exceptional, (22)

Our Quechee Escape: Spacious 5 - bedroom home in breathtaking central Vermont
Our Quechee Escape: Spacious 5 - bedroom home in breathtaking central Vermont
10.0 out of 10, Exceptional, (3)

Cozy Private Bedroom with Own Entrance - No Shower
Cozy Private Bedroom with Own Entrance - No Shower
10.0 out of 10, Exceptional, (3)
The price is AED 294
AED 448 total
includes taxes & fees
9 May - 10 May

Spacious country home, beautiful sunsets, 40 acres
Spacious country home, beautiful sunsets, 40 acres
10.0 out of 10, Exceptional, (32)

Classic Vermont Farmhouse near Sugarbush Resort
Classic Vermont Farmhouse near Sugarbush Resort
9.8 out of 10, Exceptional, (36)

☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace
☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace
9.2 out of 10, Wonderful, (36)

Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi
Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi
10.0 out of 10, Exceptional, (3)

The Shredquarters: Mid-Century Modern Chalet | 4 minutes to Snowshed 3BR/2BA
The Shredquarters: Mid-Century Modern Chalet | 4 minutes to Snowshed 3BR/2BA
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.
Save an average of 15% on thousands of hotels when you're signed in
Other property types in Pittsfield

Killington area home - 4-seasons & hot tub. Sleeps 13+
Killington area home - 4-seasons & hot tub. Sleeps 13+
9.8 out of 10, Exceptional, (117)

Private Killington Area Inn all to Yourself!
Private Killington Area Inn all to Yourself!
10.0 out of 10, Exceptional, (38)

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
9.0 out of 10, Wonderful, (42)
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.
Recent reviews of Pittsfield hotels
Recent reviews of Pittsfield hotels

North Star Lodge and Resort
5/5 Excellent
Rad Hotel
"Great hotel on the Killington access road with a rad outdoor hot pool with view of the mountain. Staff are always friendly and helpful. "
A verified traveler stayed at North Star Lodge and Resort
Posted 3 days ago
Explore a world of travel with Expedia
Explore a world of travel with Expedia
More Accommodation Types in
- Condo Rentals in Pittsfield
- Apartments in Pittsfield
- Cabin Rentals in Pittsfield
- Cottages in Pittsfield
- Chalets in Pittsfield
- Lodges in Pittsfield
- B&B in Pittsfield
- Farmstay in Pittsfield
- Aparthotels in Pittsfield
- Inns in Pittsfield
- Motels in Pittsfield
- Guest Houses in Pittsfield
- Resorts in Pittsfield
- Villas in Pittsfield
- Treehouses in Pittsfield
- Hotels