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Top Pittsfield hotels

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
$489 nightly
The price is $538 total per night from Aug 17 to Aug 18
$538 total
Aug 17 - Aug 18
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 ...
"Really enjoyed our stay."

Reviewed on Jul 18, 2025

Woodstock Inn & Resort
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road, Woodstock, VT
$252 nightly
The price is $278 total per night from Jul 23 to Jul 24
$278 total
Jul 23 - Jul 24
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 ...
"Helpfulness of the staff was first class"

Reviewed on Jul 13, 2025

On The River Inn
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
$175 nightly
The price is $192 total per night from Jul 27 to Jul 28
$192 total
Jul 27 - Jul 28
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.
"The property offers close walking distance to shops and restaurants, easy access to a grocery store, and a gorgeous view of the ŕiver."

Reviewed on Jul 17, 2025

The Shire Woodstock
Brandon Inn

Brandon Inn

3 out of 5
20 Park Street, Brandon, VT
$136 nightly
The price is $149 total per night from Jul 23 to Jul 24
$149 total
Jul 23 - Jul 24
Total includes taxes and fees
This hotel features an outdoor pool and a bar/lounge. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. ...
"Dated but cute. 3 flights of stairs to get to our room was not our favorite but room was large and comfortable. Pillows were stiff as boards. If we were there more than one night i would have asked to swap pillows. Town is adorable. I would stay again if in the area."

Reviewed on Jul 20, 2025

Brandon Inn
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 Jul 23 to Jul 24
$129 total
Jul 23 - Jul 24
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 ...
"Pleasant and quiet. Older charm, basic hotel, conveniently located and the warm outdoor pool and duck pond/fountain are great. Easy walk to the restaurant next door. Hot good coffee at 5:00 a.m. for early risers. Very clean, but the beds are a bit firm. All in all, would definitely visit again because ..."

Reviewed on Jul 20, 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
$125 nightly
The price is $138 total per night from Aug 18 to Aug 19
$138 total
Aug 18 - Aug 19
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. ...
"Hotel was good. Was a great steakhouse next door. Hotel breakfast what you would expect. No problems"

Reviewed on Jul 21, 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
$146 nightly
The price is $161 total per night from Jul 27 to Jul 28
$161 total
Jul 27 - Jul 28
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 ...
Family reunion.
"Our room was not ready when we arrived at 4:20. The person checking us in was very apologetic and offered us a glass of wine, and breakfast. We really appreciated that!"

Reviewed on Jul 20, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton
Cortina Inn

Cortina Inn

3 out of 5
476 Holiday Drive, Rutland, VT
Fully refundableReserve now, pay when you stay
$82 nightly
The price is $91 total per night from Jul 31 to Aug 1
$91 total
Jul 31 - Aug 1
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi, free self parking, and a free airport shuttle. Traveling on business? Take advantage of the ...
"Staff were extremely helpful all during my stay."

Reviewed on Jun 16, 2025

Cortina Inn
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
401 US-7, Located At The Junction Of Us 4 And Us 7, Rutland, VT
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $113 total per night from Jul 24 to Jul 25
$113 total
Jul 24 - Jul 25
Total includes taxes and fees
A restaurant and an indoor pool are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. ...
"Very nice"

Reviewed on Jul 13, 2025

Days Inn by Wyndham Rutland/Killington Area
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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 $91. 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 1,753 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

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

5 out of 5
Posted 2 days ago
Travelocity Verified Review
"Our room was not ready when we arrived at 4:20. The person checking us in was very apologetic and offered us a glass of wine, and breakfast. We really appreciated that!"
A verified traveler stayed at Killington Mountain Lodge, Tapestry Collection by Hilton
Killington Mountain Lodge, Tapestry Collection by Hilton
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