Search Resorts in Pittsfield
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Compare 4 Resorts in Pittsfield with updated reviews, rates, and availability.

Woodstock Inn & Resort
Woodstock Inn & Resort
9.2 out of 10, Wonderful, (503)
The price is SAR 1,121
SAR 1,399 total
includes taxes & fees
16 Mar - 17 Mar

The Mountain Top Inn & Resort
The Mountain Top Inn & Resort
9.0 out of 10, Wonderful, (78)
The price is SAR 775
SAR 971 total
includes taxes & fees
1 Apr - 2 Apr

Killington Weekly/Monthly/Seasonal/Holiday 5/6 Bdrms 2Game RM 2 Kit 3 LVR 4BA
Killington Weekly/Monthly/Seasonal/Holiday 5/6 Bdrms 2Game RM 2 Kit 3 LVR 4BA

On The Mountain - 1 - Bedroom - Sleeps 6
On The Mountain - 1 - Bedroom - Sleeps 6
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 Vermont Ski and Snowmobiling House
Killington Vermont Ski and Snowmobiling House
9.4 out of 10, Exceptional, (42)

Mountain Green
Mountain Green
5.8 out of 10, (8)
The price is SAR 860
SAR 1,154 total
includes taxes & fees
23 Mar - 24 Mar

Cozy Loft for two with Hot Tub & Mtn Views
Cozy Loft for two with Hot Tub & Mtn Views
10.0 out of 10, Exceptional, (233)
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

506 On the River Inn
5/5 Excellent
"Top tier property. The breakfast in particular was well done. Recommended"
A verified traveler stayed at 506 On the River Inn
Posted 2 days ago
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Popular Destinations
More Accommodation Types in Pittsfield
- Vacation Homes in Pittsfield
- 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
- Villas in Pittsfield
- Treehouses in Pittsfield
- Hotels