Book Hotels in Pittsfield, VT

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

Lincoln Inn & Gallery

Lincoln Inn & Gallery

3 out of 5
2709 West Woodstock Rd, Woodstock, VT
$235 nightly
The price is $259 total per night from Jun 2 to Jun 3
$259 total
Jun 2 - Jun 3
Total includes taxes and fees
This inn features free self parking and free WiFi in public areas. Enjoy the free self-serve breakfast each morning. A fireplace in the lobby and a picnic area ...
"Beautiful Inn and grounds."

Reviewed on May 27, 2025

Lincoln Inn & Gallery
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
$156 nightly
The price is $170 total per night from Jun 12 to Jun 13
$170 total
Jun 12 - Jun 13
Total includes 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 business center and free ...
"Great location and rooms are very clean. staff fairly knowledgeable, tho they were unable to print me out a receipt."

Reviewed on May 25, 2025

My Place Hotel-Randolph VT
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
$419 nightly
The price is $461 total per night from Jun 1 to Jun 2
$461 total
Jun 1 - Jun 2
Total includes 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 ...
"Super weekend- elegant and relaxed."

Reviewed on May 8, 2025

Woodstock Inn & Resort
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road, Woodstock, VT
$208 nightly
The price is $229 total per night from Jun 3 to Jun 4
$229 total
Jun 3 - Jun 4
Total includes taxes and fees
This hotel features an indoor pool, a hot tub, and a restaurant. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the ...
"A lovely inn, clean, well appointed in the hotel and room, hot and cold buffet breakfast , game room and pool. Had a delicious dinner at the bistro. Proximity to town- less than 5 minutes. Very glad we came for a 2 night getaway."

Reviewed on May 20, 2025

On The River Inn
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd, Killington, VT
Fully refundableReserve now, pay when you stay
$156 nightly
The price is $172 total per night from Jun 8 to Jun 9
$172 total
Jun 8 - Jun 9
Total includes 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 ...
"Cute and cozy location. Clean and all employees were very nice. The restaurant/distillery was great. The pool was nice! Walls were very thin which made it hard to sleep. Also temperature was not controllable in the room. The in room unit was not working which also made the temperature a bit uncomfortable ..."

Reviewed on May 27, 2025

The Mountain Inn at Killington
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Fully refundableReserve now, pay when you stay
$120 nightly
The price is $132 total per night from Jun 4 to Jun 5
$132 total
Jun 4 - Jun 5
Total includes 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.
"Excellent room and location"

Reviewed on May 27, 2025

The Shire Woodstock
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
$117 nightly
The price is $129 total per night from Jun 1 to Jun 2
$129 total
Jun 1 - Jun 2
Total includes 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 ...
"Quiet. Nothing happening"

Reviewed on May 12, 2025

North Star Lodge and Resort
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
$107 nightly
The price is $118 total per night from Jun 1 to Jun 2
$118 total
Jun 1 - Jun 2
Total includes 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. ...
"Check in and check out was efficient. We only stayed here for about 9 hours arriving around 11:30 at night and checking out around 8:30. Breakfast was good."

Reviewed on May 23, 2025

Comfort 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
$130 nightly
The price is $143 total per night from Jun 2 to Jun 3
$143 total
Jun 2 - Jun 3
Total includes 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 ...
"Off season rate was a great value. Draft beer in the bar $12 - not so much of value."

Reviewed on May 26, 2025

Killington 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 $118. 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 1,726 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
"Excellent room and location"
A verified traveler stayed at The Shire Woodstock
The Shire Woodstock
Explore More Ways to Travel with Travelocity

Explore More Ways to Travel with Travelocity