Hotels in Pittsfield

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The Shire Woodstock
The Shire Woodstock
3.0 star property
Woodstock
8.8 out of 10, Excellent, (918 reviews)
The price is $130
$154 total
includes taxes & fees
May 6 - May 7
The Shire Woodstock
The Vesper
The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (57 reviews)
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.
The price is $156
$172 total
includes taxes & fees
Apr 19 - Apr 20
The Vesper
Kedron Valley Inn
Kedron Valley Inn
3.5 star property
South Woodstock
9.0 out of 10, Wonderful, (334 reviews)
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.
The price is $246
$271 total
includes taxes & fees
Apr 19 - Apr 20
Kedron Valley Inn
Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 star property
Woodstock
9.4 out of 10, Exceptional, (572 reviews)
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.
The price is $309
$384 total
includes taxes & fees
Apr 20 - Apr 21
Woodstock Inn & Resort
On The River Inn
On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,005 reviews)
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.
The price is $152
$204 total
includes taxes & fees
May 6 - May 7
On The River Inn
The Jackson
The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (278 reviews)
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.
The price is $203
$223 total
includes taxes & fees
May 5 - May 6
The Jackson
Lincoln Inn & Gallery
Lincoln Inn & Gallery
3.0 star property
West Woodstock
8.8 out of 10, Excellent, (66 reviews)
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.
The price is $94
$103 total
includes taxes & fees
Apr 19 - Apr 20
Lincoln Inn & Gallery
Sleep Woodstock Motel
Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (573 reviews)
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.
The price is $81
$152 total
includes taxes & fees
May 3 - May 4
Sleep Woodstock Motel
Deer Brook Inn
Deer Brook Inn
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (1 review)
The price is $252
$278 total
includes taxes & fees
Apr 17 - Apr 18
Deer Brook Inn
My Place Hotel-Randolph VT
My Place Hotel-Randolph VT
2.0 star property
Randolph Center
9.4 out of 10, Exceptional, (426 reviews)
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.
The price is $106
$116 total
includes taxes & fees
May 10 - May 11
My Place Hotel-Randolph VT
Green Trails Inn
Green Trails Inn
3.0 star property
Brookfield
The price is $125
$137 total
includes taxes & fees
Apr 26 - Apr 27
Green Trails Inn
Killington Haus
Killington Haus
2.0 star property
Killington
9.2 out of 10, Wonderful, (39 reviews)
The price is $147
$162 total
includes taxes & fees
Apr 17 - Apr 18
Killington Haus
Killington Mountain Lodge, Tapestry Collection by Hilton
Killington Mountain Lodge, Tapestry Collection by Hilton
3.5 star property
Killington
7.4 out of 10, Good, (1,001 reviews)
The price is $139
$152 total
includes taxes & fees
Apr 22 - Apr 23
Killington Mountain Lodge, Tapestry Collection by Hilton
Killington Grand Hotel
Killington Grand Hotel
3.5 star property
Base Area
8.8 out of 10, Excellent, (210 reviews)
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.
The price is $232
$272 total
includes taxes & fees
May 17 - May 18
Killington Grand Hotel
Snowed Inn
Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (394 reviews)
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.
The price is $189
$229 total
includes taxes & fees
Apr 19 - Apr 20
Snowed Inn
Après Inn Killington
Après Inn Killington
2.0 star property
Killington
9.4 out of 10, Exceptional, (185 reviews)
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.
The price is $138
$152 total
includes taxes & fees
Apr 21 - Apr 22
Après Inn Killington
Mountain Green
Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (23 reviews)
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.
The price is $187
$251 total
includes taxes & fees
Apr 19 - Apr 20
Mountain Green
North Star Lodge and Resort
North Star Lodge and Resort
2.0 star property
Killington
8.8 out of 10, Excellent, (1,000 reviews)
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.
The price is $153
$169 total
includes taxes & fees
May 3 - May 4
North Star Lodge and Resort
The Mountain Inn at Killington
The Mountain Inn at Killington
2.5 star property
Killington
9.2 out of 10, Wonderful, (1,007 reviews)
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.
The price is $149
$172 total
includes taxes & fees
May 4 - May 5
The Mountain Inn at Killington
Breakaway House by Killington Vacation Rentals
Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
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.
Breakaway House by Killington Vacation Rentals
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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Frequently asked questions

What accommodations do travelers recommend in Pittsfield?
Can I book a refundable accommodation in Pittsfield?
If you need the flexibility to change your travel plans to Pittsfield, most accommodations provide refundable* rates you can book. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.
Where can I stay in Pittsfield if I want a vacation home instead of a hotel?
If you want a good alternative to a hotel, review our selection of 32 vacation homes.
What will the weather in Pittsfield be like during my trip?
The warmest months in Pittsfield are usually July and August with an average temp of 63°F. January and February are the chilliest months when the average temp is 23°F. The rainiest months are July and June.
Why should I book my Pittsfield hotel with Hotels.com?
There are plenty of reasons to book your Pittsfield travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.