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, (137)
9.0/10
Wonderful
(137)
The price is $165
$165
$182 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Mountain Valley Retreat
Mountain Valley Retreat
2.5 star property
Killington
9.6 out of 10, Exceptional, (191)
9.6/10
Exceptional
(191)
- Experience nature near Killington with complimentary mountain breakfasts.
The price is $110
$110
$124 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Grey Bonnet Inn
Grey Bonnet Inn
2.0 star property
Killington
7.8 out of 10, Good, (67)
7.8/10
Good
(67)
- Charming mountain lodge minutes from Killington Resort with free breakfast and WiFi.
The price is $199
$199
$219 total
includes taxes & fees
Jan 19 - Jan 20, 2026
The Mountain Top Inn & Resort
The Mountain Top Inn & Resort
3.5 star property
Chittenden
9.0 out of 10, Wonderful, (99)
9.0/10
Wonderful
(99)
- Mountainside retreat with ski-in/ski-out access and year-round outdoor adventures.
The price is $325
$325
$354 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Mountain Meadows Lodge
Mountain Meadows Lodge
3.5 star property
Killington
9.4 out of 10, Exceptional, (184)
9.4/10
Exceptional
(184)
- Experience Killington's natural beauty from this charming lodge with a hot tub.
The price is $219
$219
$266 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Greenbrier Inn
Greenbrier Inn
2.0 star property
Killington
9.4 out of 10, Exceptional, (648)
9.4/10
Exceptional
(648)
- Cozy mountainside inn near top skiing with outdoor pool and woodland trails.
The price is $189
$189
$218 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Mountain Sports Inn
Mountain Sports Inn
2.0 star property
The Woods
8.8 out of 10, Excellent, (993)
8.8/10
Excellent
(993)
- Ski country comfort with a view, just 5 minutes from Killington's best slopes.
The price is $129
$129
$142 total
includes taxes & fees
Jan 4 - Jan 5, 2026
North Star Lodge and Resort
North Star Lodge and Resort
2.0 star property
Killington
8.6 out of 10, Excellent, (1007)
8.6/10
Excellent
(1007)
- Tranquil mountain retreat near Killington Resort with outdoor pool and sauna.
The price is $160
$160
$176 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Summit Lodge
Summit Lodge
3.0 star property
Killington
8.6 out of 10, Excellent, (402)
8.6/10
Excellent
(402)
- Enjoy a cozy mountain hideaway 5 minutes from Killington Resort's top ski runs.
The price is $193
$193
$212 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Après Inn Killington
Après Inn Killington
2.0 star property
Killington
9.4 out of 10, Exceptional, (165)
9.4/10
Exceptional
(165)
- Mountain escape by Killington Resort with free WiFi and parking amenities.
The price is $185
$185
$204 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Snowed Inn
Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (374)
9.8/10
Exceptional
(374)
- Stay minutes from Killington Resort with a peaceful inn offering private hot tubs.
The price is $236
$236
$286 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Turn of River Lodge
Turn of River Lodge
2.5 star property
Killington
9.0 out of 10, Wonderful, (271)
9.0/10
Wonderful
(271)
The price is $127
$127
$139 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Alpine Court Chalet 4 Bedroom Home
Alpine Court Chalet 4 Bedroom Home
3.0 star property
Killington
- Tranquil ski lodge with a short walk to Pico Mountain and free Wi-Fi.
The price is $547
$547
$1,168 total
includes taxes & fees
Jan 11 - Jan 12, 2026
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, (1007)
7.4/10
Good
(1007)
The price is $188
$188
$207 total
includes taxes & fees
Jan 21 - Jan 22, 2026
The Suites at Killington Center
The Suites at Killington Center
3.5 star property
Killington
The price is $206
$206
$447 total
includes taxes & fees
Jan 14 - Jan 15, 2026
The Vermont Inn
The Vermont Inn
3.0 star property
Rutland
9.2 out of 10, Wonderful, (415)
9.2/10
Wonderful
(415)
- Family-friendly B&B near skiing with pool, fitness center, and complimentary perks.
The price is $285
$285
$311 total
includes taxes & fees
Jan 11 - Jan 12, 2026
The Mountain Inn at Killington
The Mountain Inn at Killington
2.5 star property
Killington
9.2 out of 10, Wonderful, (972)
9.2/10
Wonderful
(972)
- Just a few steps from Killington Resort with a free ski shuttle and slope access.
Mountain Green
Mountain Green
2.0 star property
Killington
6.8 out of 10, (17)
6.8/10
(17)
- Ski-in condo with indoor pool, just a short drive to Killington's slopes.
The price is $224
$224
$300 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Best Western Inn & Suites Rutland-Killington
Best Western Inn & Suites Rutland-Killington
2.5 star property
Rutland
8.8 out of 10, Excellent, (1002)
8.8/10
Excellent
(1002)
- Quiet ski retreat near Killington with outdoor pool and mountain access.
The price is $179
$179
$197 total
includes taxes & fees
Jan 5 - Jan 6, 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.
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.
Go beyond your typical stay in Pittsfield
Pet friendly
Apartment
Family friendly
Cottage
Condo
Check out reviews of Pittsfield hotels guests love
North Star Lodge and Resort
10/10 Excellent
"great"
Greenbrier Inn
10/10 Excellent
"The staff were very welcoming, and helpful. Wonderful place to stay. "
Brandon Inn
10/10 Excellent
"Clean room"
On The River Inn
10/10 Excellent
"The Inn was quite nice. We enjoyed the 2nd floor library area to sit and relax. The restaurant on site 506 Bistro was fabulous. "
Killington Mountain Lodge, Tapestry Collection by Hilton
10/10 Excellent
"Great resort & people even better !!! No shuttle to ski fyi so u have to have a car !! "
The Mountain Inn at Killington
10/10 Excellent
"It was our first time staying here and the experience was excellent. All the staff were very kind and helpful. The hotel’s location is excellent, and the breakfast and restaurant food were delicious. 100% recommended."
Après Inn Killington
10/10 Excellent
"Nice place to stay if you want to travel around Vermont."
Comfort Inn Rutland - Killington
10/10 Excellent
"Super clean and staff was very accommodating when I needed to change to a larger room. Great stay!"
The Shire Woodstock
10/10 Excellent
"Clean and spacious room. Check-in was quick and staff were kind and helpful."
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 30 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.