Pittsfield Hotels from S$128
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Go beyond your typical stay in Pittsfield
Pet friendly
Family friendly
Check prices for these dates
Our top choices for Pittsfield hotels
Hampton Inn Rutland
Hampton Inn RutlandRutland
9.0 out of 10, Wonderful, (1,004 reviews)
"Clean Hotel, rooms, great hot breakfast with fruits. A lot of restaurants nearby. "
Alisher
The price is S$215
includes taxes & fees
27 Apr - 28 Apr
My Place Hotel-Randolph VT
My Place Hotel-Randolph VTRandolph Center
9.4 out of 10, Exceptional, (424 reviews)
"Great place to stay!"
Chenwei
The price is S$148
includes taxes & fees
27 Apr - 28 Apr
Comfort Inn Rutland - Killington
Comfort Inn Rutland - KillingtonRutland
8.0 out of 10, Very good, (1,011 reviews)
"Clean room, comfortable bed
Great steakhouse next door"
Mark
The price is S$195
includes taxes & fees
16 Apr - 17 Apr
On The River Inn
On The River InnWest Woodstock
9.4 out of 10, Exceptional, (1,004 reviews)
"Had a lovely stay while visiting, enjoyed the breakfast and the staff were all very friendly and accommodating. Would def stay here again"
dylan
The price is S$254
includes taxes & fees
21 Apr - 22 Apr
Courtyard Middlebury
Courtyard MiddleburyMiddlebury
8.8 out of 10, Excellent, (561 reviews)
"Very clean and comfortable room. Helpful staff. "
Elizabeth
The price is S$188
includes taxes & fees
26 Apr - 27 Apr
Sleep Woodstock Motel
Sleep Woodstock MotelWoodstock
9.6 out of 10, Exceptional, (572 reviews)
"A great place to stay with pets. Rooms are a little tight, but they are clean and comfortable."
Ron
The price is S$153
includes taxes & fees
14 Apr - 15 Apr
Middlebury Sweets Motel
Middlebury Sweets MotelMiddlebury
8.6 out of 10, Excellent, (395 reviews)
"Clean spacious room and comfortable beds."
Daria
The price is S$168
includes taxes & fees
16 Apr - 17 Apr
The Mountain Inn at Killington
The Mountain Inn at KillingtonKillington
9.2 out of 10, Wonderful, (1,006 reviews)
"Great location and shuttle service. Nice breakfast and friendly staff. "
John
The price is S$197
includes taxes & fees
4 May - 5 May
Lincoln Inn & Gallery
Lincoln Inn & GalleryWest Woodstock
8.8 out of 10, Excellent, (66 reviews)
"Very pleasant and comfortable stay, about 20 mins drive to Killington nearby. Room was clean and quiet, and bed was very comfortable. Nice coffee/hot chocolate bar in the lobby but unfortunately not offering breakfast anymore."
Andrew
The price is S$128
includes taxes & fees
14 Apr - 15 Apr
Emrose Luxury Cabins
Emrose Luxury CabinsBrandon
9.0 out of 10, Wonderful, (91 reviews)
"Amazing stay"
Kelsey
The price is S$233
includes taxes & fees
21 Apr - 22 Apr
Brandon Inn
Brandon InnBrandon
8.8 out of 10, Excellent, (609 reviews)
"Loved The Brandon Inn. Kind staff, cozy atmosphere, great location and a warm room.
I will be returning here!!!"
David J.
The price is S$164
includes taxes & fees
15 Apr - 16 Apr
Best Western Inn & Suites Rutland-Killington
Best Western Inn & Suites Rutland-KillingtonRutland
8.8 out of 10, Excellent, (1,004 reviews)
"Excellent stay for the price."
Anthony
The price is S$226
includes taxes & fees
20 Apr - 21 Apr
The Shire Woodstock
The Shire WoodstockWoodstock
8.8 out of 10, Excellent, (918 reviews)
"Wonderful place to stay!"
Robin
The price is S$208
includes taxes & fees
6 May - 7 May
Mountain Sports Inn
Mountain Sports InnKillington
8.8 out of 10, Excellent, (1,004 reviews)
"Clean, great breakfast, room is a little small"
Ziye
The price is S$139
includes taxes & fees
20 Apr - 21 Apr
The Jackson
The JacksonWest Woodstock
9.6 out of 10, Exceptional, (277 reviews)
"Easy Check-In; Lovely Room; Great Location & Atmosphere. The staff was very friendly,"
Michael
The price is S$268
includes taxes & fees
6 May - 7 May
Mountain Meadows Lodge
Mountain Meadows LodgeKillington
9.6 out of 10, Exceptional, (210 reviews)
"Great place for our ski trip"
Mohammad
The price is S$231
includes taxes & fees
7 May - 8 May
North Star Lodge and Resort
North Star Lodge and ResortKillington
8.8 out of 10, Excellent, (1,001 reviews)
"Nice place to stay and room had a view of Superstar slope. "
Rick
The price is S$186
includes taxes & fees
8 May - 9 May
The Vermont Inn
The Vermont InnRutland
9.2 out of 10, Wonderful, (427 reviews)
"Greeted with cookies and a cozy living room with games and cute decorations. Nice, clean room with a comfortable bed. Breakfast was great (fresh berries, make your own waffles, muffins, etc). Breakfast is at 8 so you may not make first tracks in the slopes"
Piruz
The price is S$270
includes taxes & fees
3 May - 4 May
The Mountain Top Inn & Resort
The Mountain Top Inn & ResortChittenden
9.0 out of 10, Wonderful, (116 reviews)
"Great resort "
Adam
The price is S$205
includes taxes & fees
19 Apr - 20 Apr
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
Stay near popular Pittsfield attractions
Top Pittsfield Hotel Reviews
Days Inn by Wyndham Rutland/Killington Area
4/10 Poor
More cheap stays in Pittsfield
My Place Hotel-Randolph VT
2440 Vermont 66 Randolph Center VT
The price is S$148 per night from 27 Apr to 28 Apr
S$148
27 Apr - 28 Apr
includes taxes & fees
Frequently asked questions
Explore a world of travel with Expedia
- Belmont Hotels
- Benson Hotels
- Resorts in Benson
- Cabin Rentals in Berlin Corners
- Bethel Hotels
- Brandon Hotels
- Brookfield Hotels
- B&B in Castleton
- Castleton Hotels
- Cabin Rentals in Cavendish
- Villas in Cavendish
- Apartments in Central Vermont
- Boutique Hotels in Central Vermont
- Resorts in Central Vermont
- Chittenden Hotels
- Condo Rentals in Cornwall
- Hotels with free parking in Vermont
- Cabin Rentals in Fair Haven
- Goshen Hotels
- Granville Hotels
- Luxury Hotels in Killington
- Killington Hotels
- Motels in Killington
- Hotels near Killington Resort
- Cottages in Leicester
- Leicester Hotels
- Hotels with Gyms in Ludlow
- Mendon Hotels
- North Clarendon Hotels
- Hotels near Pico Mountain at Killington Ski Resort
- Quechee Hotels
- Randolph Hotels
- Reading Hotels
- Ripton Hotels
- Rochester Hotels
- Roxbury Hotels
- Rutland Hotels
- Hotels near Rutland Southern Vermont Regional
- Sharon Hotels
- Hotels near Silver Lake State Park
- South Royalton Hotels
- South Woodstock Hotels
- Hotels with Balcony in Stockbridge
- Condo Rentals in Vermont
- Motels in Vermont
- Wallingford Hotels
- Hotels with Swimming Pools in Warren
- Warren Hotels
- Hotels with smoking rooms in White River Junction
- Resorts in Windsor
- Woodstock Hotels
- Flights to Killington
- Flights to Ludlow
- Flights to Middlebury
- Flights to Waitsfield
- Flights to White River Junction
- Flights to Vermont
- Flights from Killington
- Flights from Wilder
- Flights from Norwich
- Flights from Perkinsville
- Flights from North Clarendon
- Flights from Sharon
- Flights from Danby
- Flights from Central Vermont
- Flights from Castleton
- Flights from Bethel
- Flights from Ludlow
- Flights from Chelsea
- Flights from Guaymas (GYM) to Rutland (RUT)
- Flights from Chicago (ORD) to Rutland (RUT)
- Flights from Sanya (SYX) to Montpelier (MPV)
- Visit Andover
- Visit Barre
- Bear Mountain Quad Ski Lift
- Branbury State Park
- Calvin Coolidge Historic Site
- Castleton University
- Diamond Run Mall
- Visit Fairlee
- Fire Tower
- Gifford Woods State Park
- Green Mountain National Golf Course
- Green Mountain Rock Climbing Center
- Halpin Covered Bridge
- Killington Golf Course
- Killington Peak
- Visit Moretown
- Visit Mount Tabor
- Visit Orwell
- Pico Mountain at Killington Ski Resort
- Practice Slope Chair Lift
- Proctor-Pittsford Country Club
- Saskadena Six Ski Area
- Skinner Barn
- Visit South Woodstock
- Visit Strafford
