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Top Pittsfield hotels

Killington area home - 4-seasons, hot tub and A/C

Killington area home - 4-seasons, hot tub and A/C

Pittsfield VT
A hot tub is featured at this vacation home, along with a garden and laundry facilities. There's fun for all ages with a playground and an arcade/game room, ...
"House was very nice overall. Spacious and well laid out. Certain things felt a little dirty - grout in the showers, the bedding, etc. Nothing egregious, just not pristinely clean."

Reviewed on Jul 20, 2026

Get rates
Opens in a new windowKillington area home - 4-seasons, hot tub and A/C
The Jackson

The Jackson

4 out of 5
43 Senior Lane Woodstock VT
$179 nightly
The price is $197 total per night from Jul 28 to Jul 29
$197 total
Jul 28 - Jul 29
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, ...
"Staffing was basically non-existent with a machine generated welcome and check out. Property website stated “Food is a central component of every stay here at our Woodstock, VT Bed and Breakfast - and we take immeasurable pride in it. Our breakfast is a European-style breakfast…”which we assumed ..."

Reviewed on Jul 18, 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 Aug 16 to Aug 17
$527 total
Aug 16 - Aug 17
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 ...
"I am terribly sorry to give such a bad review. They put us in the basement they call ground level, the room smelled dank and like mold. Everything stayed wet..towels bathing suits. The people were nice. The elevator smelled like urin and puke..they charge a incidentale fee of 250 dollars a day that ..."

Reviewed on Jul 16, 2026

Opens in a new windowWoodstock Inn & Resort
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
$239 nightly
The price is $263 total per night from Jul 26 to Jul 27
$263 total
Jul 26 - Jul 27
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 ...
"Is just charming, peaceful and with that Vermont character."

Reviewed on Jul 20, 2026

Opens in a new windowOn The River Inn
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
$117 nightly
The price is $127 total per night from Aug 2 to Aug 3
$127 total
Aug 2 - Aug 3
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 ...
"The room was clean. Plenty of towels. Bed blankets are a bit odd"

Reviewed on Jul 20, 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
Fully refundableReserve now, pay when you stay
$156 nightly
The price is $172 total per night from Jul 21 to Jul 22
$172 total
Jul 21 - Jul 22
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 ...
"We enjoyed our stay here, it is a great location to the mountain and the staff (and owner) were friendly and fun to talk with. My only recommendation is to get on the upper floor if you can. We had a family staying above us and we heard every step late into the evening and early the next morning, ..."

Reviewed on Jul 20, 2026

Opens in a new windowThe Mountain Inn at Killington
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St. Woodstock VT
$293 nightly
The price is $322 total per night from Aug 18 to Aug 19
$322 total
Aug 18 - Aug 19
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.
"There for one night. Stayed in the river house. Room was good. Very quiet. The fire pits and sitting area along the river was fantastic. Sat out there at night after dinner and for coffee the next morning."

Reviewed on Jul 18, 2026

Opens in a new windowThe Shire Woodstock
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St Rutland VT
Fully refundable
$116 nightly
The price is $128 total per night from Jul 26 to Jul 27
$128 total
Jul 26 - Jul 27
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. ...
"Good breakfast"

Reviewed on Jul 19, 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
$139 nightly
The price is $152 total per night from Jul 26 to Jul 27
$152 total
Jul 26 - Jul 27
Total with taxes and fees
This hotel features a 24-hour gym and a hot tub. Traveling on business? Take advantage of the 2 conference rooms, along with free WiFi in public areas. Self ...
"The property is absolutely gorgeous. Front desk was great. The room I got had a skylite, which is nice but the sun was right in the pillows of the bed, so in the afternoon, if you wanted to take a rest from your days activities, you couldn’t due to the sun being in the pillows, and no way to block ..."

Reviewed on Jul 15, 2026

Opens in a new windowKillington Mountain Lodge, Tapestry Collection by Hilton
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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 $127. 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 1,830 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

On The River Inn

On The River Inn

5 out of 5
Posted less than an hour ago
Travelocity Verified Review
"Is just charming, peaceful and with that Vermont character."
A verified traveler stayed at On The River Inn
On The River Inn

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