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Our top choices for Pittsfield hotels
8.8 out of 10, Excellent, (895)
Tucked in charming Woodstock, this welcoming hotel provides complimentary WiFi, parking, and bicycle rentals for exploring nearby trails. Guests praise the helpful staff and spotless rooms, with Billings Park and Red Wagon Toy Company just moments away.
"Wonderful place to stay!"
Robin
9.6 out of 10, Exceptional, (551)
Enjoy a peaceful retreat near Killington and Sugarbush ski resorts. This well-maintained motel offers clean rooms and friendly staff in a beautiful Vermont setting. Free WiFi and parking make it easy to explore Ottaquechee River and local hiking trails.
"The staff at this motel are 5 star! Lisa went above and beyond to make my stay easy since I was there for a medical procedure. "
Crystal
The price is NZ$256
includes taxes & fees
6 Jan - 7 Jan 2026
9.8 out of 10, Exceptional, (259)
Victorian charm awaits at this quiet Woodstock B&B where travellers rave about the delicious morning meal. Relax in the garden, enjoy evening drinks at the bar, or explore nearby Union Arena and Five Elm Arches from this peaceful retreat.
"The Jackson Inn is incredibly charming and in a picturesque area. The room was very comfortable and the restaurant and staff was amazing."
Abby
9.0 out of 10, Wonderful, (271)
Wake to mountain adventures at this cosy Vermont lodge. Just minutes from Killington and Pico Mountain ski resorts, guests enjoy free continental breakfast and parking. Mountain biking trails await nearby, with 24-hour front desk staff ready to assist throughout your stay.
"Was amazing ill be back"
Jacob
The price is NZ$240
includes taxes & fees
4 Jan - 5 Jan 2026
9.4 out of 10, Exceptional, (1004)
Discover a tranquil retreat near the train station in Woodstock featuring an indoor pool, spa pool, and on-site 506 Bistro and Lounge. Guests love the helpful staff, complimentary breakfast, and convenient access to Union Arena Community Centre.
"Brilliant stay"
Enrico
9.6 out of 10, Exceptional, (191)
Experience mountain adventures from this tranquil B&B offering complimentary full breakfast, WiFi, and parking. Outdoor enthusiasts can enjoy nearby hiking, biking, and kayaking, plus easy access to Pico Mountain and Killington ski areas.
"This was my third stay with Mike and Barbara. It's just so lovely in a beautiful rural setting! And sure can't complain about the hearty breakfasts cooked by Chef Mike. It's certain I'll return on another ski adventure to Killington."
Kathy
The price is NZ$214
includes taxes & fees
22 Jan - 23 Jan 2026
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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Stay near popular Pittsfield attractions
More cheap accommodation in Pittsfield
My Place Hotel-Randolph VT
2440 Vermont 66 Randolph Center VT
The price is NZ$194 per night from 25 Jan to 26 Jan
NZ$194
25 Jan - 26 Jan 2026
includes taxes & fees
9.2/10 Wonderful! (354 reviews)
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