Hotels in Pittsfield

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The Trailside Inn
The Trailside Inn
3.0 star property
North Sherburne
9.0 out of 10, Wonderful, (141 reviews)
The price is $165
$182 total
includes taxes & fees
Jan 19 - Jan 20
The Trailside Inn
Mountain Valley Retreat
Mountain Valley Retreat
2.5 star property
Killington
9.6 out of 10, Exceptional, (194 reviews)
  • cleanliness
    Experience nature near Killington with complimentary mountain breakfasts.
The price is $110
$124 total
includes taxes & fees
Jan 19 - Jan 20
Mountain Valley Retreat
Grey Bonnet Inn
Grey Bonnet Inn
2.0 star property
Killington
7.8 out of 10, Good, (68 reviews)
  • cleanliness
    Charming mountain lodge minutes from Killington Resort with free breakfast and WiFi.
The price is $164
$180 total
includes taxes & fees
Feb 1 - Feb 2
Grey Bonnet Inn
The Mountain Top Inn & Resort
The Mountain Top Inn & Resort
3.5 star property
Chittenden
9.0 out of 10, Wonderful, (101 reviews)
  • cleanliness
    Mountainside retreat with ski-in/ski-out access and year-round outdoor adventures.
The price is $260
$283 total
includes taxes & fees
Jan 19 - Jan 20
The Mountain Top Inn & Resort
Greenbrier Inn
Greenbrier Inn
2.0 star property
Killington
9.4 out of 10, Exceptional, (653 reviews)
  • cleanliness
    Cozy mountainside inn near top skiing with outdoor pool and woodland trails.
The price is $194
$224 total
includes taxes & fees
Jan 19 - Jan 20
Greenbrier Inn
Mountain Sports Inn
Mountain Sports Inn
2.0 star property
The Woods
8.8 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Ski country comfort with a view, just 5 minutes from Killington's best slopes.
The price is $109
$120 total
includes taxes & fees
Jan 21 - Jan 22
Mountain Sports Inn
Killington A-frame 2 Bedroom Home
Killington A-frame 2 Bedroom Home
3.0 star property
North Sherburne
  • cleanliness
    Ski retreat close to Green Mountain course, offering trail access and garden views.
The price is $448
$897 total
includes taxes & fees
Feb 5 - Feb 6
Killington A-frame 2 Bedroom Home
North Star Lodge and Resort
North Star Lodge and Resort
2.0 star property
Killington
8.6 out of 10, Excellent, (1,004 reviews)
  • cleanliness
    Tranquil mountain retreat near Killington Resort with outdoor pool and sauna.
The price is $160
$176 total
includes taxes & fees
Jan 19 - Jan 20
North Star Lodge and Resort
Summit Lodge
Summit Lodge
3.0 star property
Killington
8.6 out of 10, Excellent, (409 reviews)
  • cleanliness
    Enjoy a cozy mountain hideaway 5 minutes from Killington Resort's top ski runs.
The price is $193
$212 total
includes taxes & fees
Jan 20 - Jan 21
Summit Lodge
The Suites at Killington Center
The Suites at Killington Center
3.5 star property
Killington
The price is $142
$376 total
includes taxes & fees
Jan 19 - Jan 20
The Suites at Killington Center
Après Inn Killington
Après Inn Killington
2.0 star property
Killington
9.4 out of 10, Exceptional, (170 reviews)
  • cleanliness
    Mountain escape by Killington Resort with free WiFi and parking amenities.
The price is $176
$194 total
includes taxes & fees
Jan 19 - Jan 20
Après Inn Killington
Snowed Inn
Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (375 reviews)
  • cleanliness
    Stay minutes from Killington Resort with a peaceful inn offering private hot tubs.
The price is $213
$258 total
includes taxes & fees
Jan 20 - Jan 21
Snowed Inn
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, (1,003 reviews)
The price is $163
$180 total
includes taxes & fees
Jan 20 - Jan 21
Killington Mountain Lodge, Tapestry Collection by Hilton
Turn of River Lodge
Turn of River Lodge
2.5 star property
Killington
8.8 out of 10, Excellent, (273 reviews)
The price is $127
$139 total
includes taxes & fees
Jan 19 - Jan 20
Turn of River Lodge
The Vermont Inn
The Vermont Inn
3.0 star property
Rutland
9.2 out of 10, Wonderful, (415 reviews)
  • cleanliness
    Family-friendly B&B near skiing with pool, fitness center, and complimentary perks.
The price is $285
$311 total
includes taxes & fees
Jan 19 - Jan 20
The Vermont Inn
The Mountain Inn at Killington
The Mountain Inn at Killington
2.5 star property
Killington
9.2 out of 10, Wonderful, (980 reviews)
  • cleanliness
    Just a few steps from Killington Resort with a free ski shuttle and slope access.
The price is $249
$288 total
includes taxes & fees
Jan 19 - Jan 20
The Mountain Inn at Killington
Killington Ski Resort VT Vacation Condos
Killington Ski Resort VT Vacation Condos
3.5 star property
Killington
  • cleanliness
    Wake up to the thrill of skiing with easy access to Killington and Pico Mountain.
The price is $157
$367 total
includes taxes & fees
Jan 21 - Jan 22
Killington Ski Resort VT Vacation Condos
Mountain Green
Mountain Green
2.0 star property
Killington
7.0 out of 10, Good, (19 reviews)
  • cleanliness
    Ski-in condo with indoor pool, just a short drive to Killington's slopes.
The price is $235
$315 total
includes taxes & fees
Feb 10 - Feb 11
Mountain Green
Best Western Inn & Suites Rutland-Killington
Best Western Inn & Suites Rutland-Killington
2.5 star property
Rutland
8.8 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Quiet ski retreat near Killington with outdoor pool and mountain access.
The price is $179
$197 total
includes taxes & fees
Jan 25 - Jan 26
Best Western Inn & Suites Rutland-Killington
Emrose Luxury Cabins
Emrose Luxury Cabins
2.0 star property
Brandon
9.0 out of 10, Wonderful, (70 reviews)
  • cleanliness
    Experience wilderness retreat near Brandon with luxurious cabins and private hot tubs.
The price is $200
$226 total
includes taxes & fees
Jan 18 - Jan 19
Emrose Luxury Cabins
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 29 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.