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Top Pittsfield hotels

Mountain Meadows Lodge

Mountain Meadows Lodge

3.5 out of 5
285 Thundering Brook Road Killington VT
$157 nightly
The price is $172 total per night from Oct 26 to Oct 27
$172 total
Oct 26 - Oct 27
Total with taxes and fees
This hotel features a hot tub and a sauna. Families will appreciate the arcade/game room and picnic area. Relax with a drink at the bar/lounge and enjoy the ...
"The farmhouse room was small and not to the standards of the lodge room. Our group all booked at the same time and our similar priced room was did not include a deck or the other amenities. The staff was superior and the general facility was incredible. Not sure why we were placed in a room that ..."

Reviewed on Oct 7, 2026

Opens in a new windowMountain Meadows Lodge
The Jackson

The Jackson

4 out of 5
43 Senior Lane Woodstock VT
$150 nightly
The price is $165 total per night from Nov 3 to Nov 4
$165 total
Nov 3 - Nov 4
Total with taxes and fees
A restaurant and a bar/lounge are featured at this bed & breakfast. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, ...
"Evelyn & Oakes was top notch."

Reviewed on Oct 6, 2026

Opens in a new windowThe Jackson
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$479 nightly
The price is $527 total per night from Nov 2 to Nov 3
$527 total
Nov 2 - Nov 3
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 ...
"Lovely feel to the hotel with friendly staff. Room was comfortable and location is excellent. Love Woodstock as a destination. I am never the biggest fan of breakfast, but really enjoyed it for once"

Reviewed on Oct 7, 2026

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
$105 nightly
The price is $115 total per night from Nov 8 to Nov 9
$115 total
Nov 8 - Nov 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 ...
"Great location nice new hotel, no food services and the hotel appeared like it had just opened. At the price we would have expected much more"

Reviewed on Oct 8, 2026

Opens in a new windowMy Place Hotel-Randolph VT
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
$183 nightly
The price is $202 total per night from Nov 1 to Nov 2
$202 total
Nov 1 - Nov 2
Total with 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 ...
"Very accommodating and helpful staff. Rooms were clean but missing amenities. No coffee. No glasses for water. Possibly an oversight"

Reviewed on Oct 7, 2026

Opens in a new windowOn The River Inn
Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
1246 Franklin Street Brandon VT
$192 nightly
The price is $210 total per night from Nov 8 to Nov 9
$210 total
Nov 8 - Nov 9
Total with taxes and fees
This hotel's 8 hot tubs and 24-hour gym are among the featured amenities. Families will appreciate the arcade/game room and picnic area. Enjoy the seasonal outdoor ...
"The room had an overpowering smell of cleaning products, and the only ventilation was a small bathroom window, so there was no real way to air it out. The property sits right off the highway, and traffic noise carried through the night, which made it hard to sleep. The space felt like it was put ..."

Reviewed on Oct 8, 2026

Opens in a new windowEmrose Luxury Cabins
Mountain Sports Inn

Mountain Sports Inn

2 out of 5
813 Killington Road Killington VT
$139 nightly
The price is $153 total per night from Oct 12 to Oct 13
$153 total
Oct 12 - Oct 13
Total with taxes and fees
A restaurant, free self parking, and a communal living room are among this hotel's amenities. Guests will appreciate free perks like full breakfast and WiFi ...
"The staff was very good and the breakfast was excellent thanks to all."

Reviewed on Oct 7, 2026

Opens in a new windowMountain Sports Inn
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St Rutland VT
Fully refundable
$123 nightly
The price is $136 total per night from Nov 1 to Nov 2
$136 total
Nov 1 - Nov 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. ...
"Clean room, good staff, good breakfast"

Reviewed on Oct 8, 2026

Opens in a new windowComfort Inn Rutland - Killington
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 Oct 19 to Oct 20
$172 total
Oct 19 - Oct 20
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 ...
Opens in a new windowThe Mountain Inn at Killington
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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 $115. 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 1,845 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

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

4 out of 5
Posted 9 hours ago
Travelocity Verified Review
"Clean room, good staff, good breakfast"
A verified traveler stayed at Comfort Inn Rutland - Killington
Comfort Inn Rutland - Killington

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