Book Hotels in Pittsfield, VT

Start date: Check-in selected.
To Date
End date: Check-out

Cabins, apartments, houseboats! We offer comfortable & private vacation rentals

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Filter by

Guest rating
Guest rating
Star rating
Payment type
Payment type
Property type
Property type
Neighborhood
Neighborhood
Traveler experience
Traveler experience
Popular locations
Popular locations
Meal plans available
Meal plans available
Amenities
Amenities
Accessibility
Accessibility

Top Pittsfield hotels

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$429 nightly
The price is $472 total per night from Jan 20 to Jan 21
$472 total
Jan 20 - Jan 21
Total with taxes and fees
This luxury resort features a golf course, a full-service spa, and 4 restaurants. Enjoy the 2 indoor tennis courts and perks like free valet parking and free ...
Luxurious and friendly resort! Loved it

Reviewed on Dec 18, 2025

Opens in a new windowWoodstock Inn & Resort
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
2440 Vermont 66 Randolph Center VT
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $107 total per night from Feb 8 to Feb 9
$107 total
Feb 8 - Feb 9
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling on business? Take advantage of the 24-hour business center and ...
This is a newer hotel. Rooms were very clean, staff was kind, nice and quiet. Full sized fridge in the room. Only 3 floors which was nice because I cant take elevators. I travel to this area about 8 times a year and will definitely stay here again.

Reviewed on Jan 11, 2026

Opens in a new windowMy Place Hotel-Randolph VT
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd Killington VT
$261 nightly
The price is $288 total per night from Jan 20 to Jan 21
$288 total
Jan 20 - Jan 21
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the free ski shuttle and onsite ski storage. Enjoy the gym and free perks like continental ...
Everyone was friendly, courteous, and helpful. Room was very clean. Restaurant and bar had live music. Overall place was A+

Reviewed on Jan 17, 2026

Opens in a new windowThe Mountain Inn at Killington
Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington

2.5 out of 5
5 Best Western Place Rutland VT
Fully refundableReserve now, pay when you stay
$179 nightly
The price is $197 total per night from Jan 26 to Jan 27
$197 total
Jan 26 - Jan 27
Total with taxes and fees
This hotel features a 24-hour gym and an outdoor tennis court. Enjoy the free ski shuttle and onsite ski storage. Enjoy the seasonal outdoor pool and free perks ...
Very easy to get to, very clean and spacious room and excellent staff attention

Reviewed on Jan 10, 2026

Opens in a new windowBest Western Inn & Suites Rutland-Killington
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
78 Weathervane Dr Killington VT
Fully refundableReserve now, pay when you stay
$160 nightly
The price is $176 total per night from Jan 21 to Jan 22
$176 total
Jan 21 - Jan 22
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Families will appreciate the arcade/game room and onsite laundry facilities. Enjoy the gym ...
Location was good. Easy check in

Reviewed on Jan 16, 2026

Opens in a new windowNorth Star Lodge and Resort
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St. Woodstock VT
Fully refundableReserve now, pay when you stay
$131 nightly
The price is $144 total per night from Jan 21 to Jan 22
$144 total
Jan 21 - Jan 22
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and a picnic area are also provided.
Cozy comfortable room for a fair price. Easy check-in and check-out.

Reviewed on Jan 17, 2026

Opens in a new windowThe Shire Woodstock
Summit Lodge

Summit Lodge

3 out of 5
200 Summit Road Killington VT
$193 nightly
The price is $212 total per night from Jan 20 to Jan 21
$212 total
Jan 20 - Jan 21
Total with taxes and fees
This smoke-free inn features 2 outdoor pools, a hot tub, and a restaurant. Enjoy the seasonal outdoor pool and free perks like full breakfast and free self parking. ...
Nice staff. Kind

Reviewed on Jan 14, 2026

Opens in a new windowSummit Lodge
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St Rutland VT
Fully refundableReserve now, pay when you stay
$140 nightly
The price is $154 total per night from Feb 1 to Feb 2
$154 total
Feb 1 - Feb 2
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. ...
Very comfortable stay. Only stayed one night. Everything was as expected. Updated rooms and bathrooms. Clean and comfortable.

Reviewed on Jan 9, 2026

Opens in a new windowComfort Inn Rutland - Killington
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd Killington VT
Fully refundableReserve now, pay when you stay
$171 nightly
The price is $189 total per night from Jan 28 to Jan 29
$189 total
Jan 28 - Jan 29
Total with taxes and fees
This hotel features a 24-hour gym and a hot tub. There's a free ski shuttle, and ski passes and ski storage are available on site. WiFi in public areas is ...
Solid accommodations.

Reviewed on Jan 12, 2026

Opens in a new windowKillington Mountain Lodge, Tapestry Collection by Hilton
Don't see what you're looking for?
See all available properties in Pittsfield
View all properties
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.

Pittsfield Hotel & Travel Guide\n

Visiting Central Vermont- Killington and hoping to find basic or more upscale accommodations in Pittsfield? There are a limited number of options which can be booked through Travelocity's reservations page. You'll find 2 hotels, apartments and other accommodation options in Pittsfield that will fit the bill.

Travelocity-listed hotels within a quick drive of Pittsfield include the The Mountain Top Inn & Resort and The Trailside Inn.

The Killington Grand Resort Hotel is positioned 11 miles (18 kilometers) away from the heart of Pittsfield. An alternative place to stay is the Mountain Green Ski & Golf Resort, which is located 11 miles (18 kilometers) away. Another possibility is to make a booking at the Mendon Mountainview Lodge or the The Red Clover Inn & Restaurant.

When you are keen to discover some more of the forests typical in this part of the world, you might also take some time in other destinations in Central Vermont. Have fun snowboarding and skiing or enjoy the region's intriguing cultural and natural attractions. Family-friendly Travelocity-registered hotel options await you.

Killington is 11 miles (17 kilometers) southeast of Pittsfield and boasts Killington Ski Resort and Green Mountain National Golf Course. The North Star Lodge and Resort and Killington Center Inn & Suites are just some of the convenient hotel and apartment choices in Killington. 14 miles (23 kilometers) south of Pittsfield, you may also choose to stay at Rutland, which is home to the Hampton Inn Rutland and Holiday Inn Rutland-Killington Area. If you stay in Rutland, a couple of places to add to your itinerary are the Pine Hill Park and Vermont State Fairgrounds.

Make sure you get your serving of sport by taking a journey to Glens Falls Civic Center, which can be found 50 miles (80 kilometers) to the southwest of Pittsfield. Travelocity readers who enjoy the ease of booking a room close to the game, make a reservation in the The Glens Falls Inn or Sleep Inn & Suites.

Before you and your traveling partner head towards Pittsfield, put aside some time to browse our Pittsfield hotel and travel page where you'll find out about the numerous attractions on offer.

Frequently asked questions

What are the top kid-friendly hotels in Pittsfield?
Take some of the hassles out of traveling with young ones by choosing a family-friendly hotel in Pittsfield. From useful amenities to services that bring a smile, these stays feature perks that'll make your getaway plain sailing: The whole gang will love staying at Wintergreen 106 in Pittsfield. Housekeeping services and a fireplace are just a couple of the things that help make this hotel a sought-after option. Also look into Perfect secluded cozy getaway home Hawk Landing. It offers a water park, a nearby theme park and ample opportunities for family time.
Where can I find cheap hotels in Pittsfield?
At Travelocity you'll find really nice hotels in Pittsfield at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Pittsfield rather than in Pittsfield. We may find you even better rates, too.
How do I find the best Pittsfield hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Pittsfield then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Pittsfield?
The cheapest hotel in Pittsfield is $107. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Pittsfield?
There are 1,800 hotels in Pittsfield on Travelocity.
What are the best hotels in Pittsfield?
Pittsfield has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Pittsfield for you!
When is the best time to visit Pittsfield?
If you want the joy of a fun-filled trip in peak season, visit Pittsfield during November, December and January. If you'd prefer the peace of off-season, book a stay during quieter months, such as April, May and June.
When is the cheapest time to stay in Pittsfield?
Based on historic data is usually the cheapest month to visit Pittsfield. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Pittsfield?
There are multiple hotels in Pittsfield that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Pittsfield. We have plenty of kid-friendly hotels in Pittsfield to choose from on Travelocity!
Why book a hotel in Pittsfield through Travelocity?
Because we have the top hotels in Pittsfield! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Pittsfield on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Pittsfield hotel reviews by fellow wanderers

The Shire Woodstock

The Shire Woodstock

5 out of 5
Posted 2 days ago
Travelocity Verified Review
"Cozy comfortable room for a fair price. Easy check-in and check-out."
A verified traveler stayed at The Shire Woodstock
The Shire Woodstock

Explore More Ways to Travel with Travelocity