Hotels in Pittsfield

Wake to complimentary continental breakfast at this charming Woodstock B&B. Enjoy nearby cross-country skiing and snowboarding, then return to free WiFi and parking. Billings Park and Trail and Dana House Museum are just minutes away.

Set in charming South Woodstock, Kedron Valley Inn puts you near Union Arena Community Center and VINS Nature Center. After exploring, enjoy dinner at Ransom Tavern or unwind with drinks on the terrace.

Unwind at this elegant Vermont resort with golf course, spa, and indoor pool near Middle Covered Bridge. Four restaurants serve American cuisine, while two bars offer evening relaxation. Travelers praise the attentive staff and central location.

Set along the waters of Woodstock, this family-friendly hotel offers an indoor pool, hot tub, and fitness center. Grab a bite at 506 Bistro and Lounge before exploring Union Arena or Five Elm Arches. Free WiFi and parking round out this relaxing riverside retreat.

This peaceful B&B offers a quiet retreat with Victorian charm and lush gardens. Enjoy the on-site restaurant and unwind at the stylish bar after exploring nearby Five Elm Arches. Guests rave about the delicious breakfast and convenient free WiFi and parking.

Tucked in charming Woodstock, this inn provides a cozy retreat with a welcoming fireplace in the lobby. Explore the nearby Union Arena Community Center or wander along the scenic Ottaquechee River. Convenient free WiFi and self parking make your Vermont adventure seamless.

Set in a serene landscape just outside Woodstock, this cozy motel offers the perfect basecamp for Killington and Sugarbush skiing adventures. Clean, peaceful rooms welcome you after days of outdoor exploration. Enjoy free WiFi, parking, and proximity to the Ottaquechee River.

This business-friendly hotel in Randolph Center offers complimentary WiFi and parking near Whale Dance Sculpture and Montague Golf Club. Just 6 minutes from Randolph Station and 24 minutes from Montpelier airport, with round-the-clock front desk assistance.

Embrace alpine adventure at this ski-in/ski-out haven featuring 2 hot tubs and an outdoor pool. After thrilling runs at Killington Resort, relax at the full-service spa. The bar and restaurant offer perfect après-ski unwinding near Pico Mountain.

Escape to this cozy B&B near prime skiing at Killington and Pico Mountain. Unwind in private hot tubs after a day on the slopes, or stroll to nearby restaurants and shops. The quiet, homey atmosphere lets you fall asleep to natural sounds with windows open.

Surrounded by Vermont's mountains, this cozy inn offers a peaceful stay just minutes from Killington and Pico ski resorts. Enjoy free WiFi and parking, plus a charming picnic area for outdoor relaxation after slopes adventures.

Warm mountain escape with ski-trail access and an indoor pool for year-round relaxation. Enjoy free parking and nearby hiking trails while staying close to both Killington Resort and Pico Mountain for thrilling winter adventures.

Just 5 minutes from Killington Resort, this quiet lodge offers a peaceful mountain escape. Dive into the outdoor pool, relax in the sauna after skiing, or enjoy a meal at the restaurant with a drink at the bar.

Experience the ultimate ski vacation with slopeside convenience. This mountain retreat offers free breakfast and parking, plus an outdoor pool to relax after hitting the slopes. Near both Killington and Pico Mountain resorts, you'll appreciate the helpful staff and cozy bar/lounge.

Wake up to adventure in this Killington vacation home with free WiFi. Located within a 10-minute drive of both Killington Resort and Pico Mountain, you'll find the perfect base for skiing thrills and mountain exploration.