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May 10 - May 12

Top Pittsfield hotels

Comfort Inn Trolley Square

Comfort Inn Trolley Square

2.5 out of 5
19 Allen St, Rutland, VT
Free Cancellation
Reserve now, pay when you stay
14.43 mi from city center
The price is $123 per night
$123
per night
May 5 - May 6
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. Enjoy the spa tub and free perks like buffet breakfast and free self parking.
Hot Tub
Breakfast included
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd, Killington, VT
Free Cancellation
Reserve now, pay when you stay
9.49 mi from city center
The price is $134 per night
$134
per night
May 19 - May 20
This hotel features a 24-hour gym and a spa tub. There's a free ski shuttle, and ski passes and ski storage are available on site. WiFi in public areas is free.
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
Free Cancellation
Reserve now, pay when you stay
15.08 mi from city center
The price is $101 per night
$101
per night
May 15 - May 16
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. A restaurant, a 24-hour front desk, and express check-out are also provided.
Pet friendly
Breakfast included
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
78 Weathervane Dr, Killington, VT
Free Cancellation
Reserve now, pay when you stay
8.06 mi from city center
The price is $108 per night
$108
per night
Jun 3 - Jun 4
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 and perks like free self parking and free WiFi.
Pool
Parking included
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
17.93 mi from city center
The price is $289 per night
$289
per night
May 5 - May 6
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 WiFi. Relax with a drink at one of the 2 bars/lounges and enjoy the 2 spa tubs and indoor pool.
Hot Tub
Pet friendly
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd, Killington, VT
Free Cancellation
Reserve now, pay when you stay
9.83 mi from city center
The price is $132 per night
$132
per night
Jun 2 - Jun 3
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 breakfast and free self parking.
Pet friendly
Breakfast included
Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington

2.5 out of 5
5 Best Western Place, Rutland, VT
Free Cancellation
Reserve now, pay when you stay
11.32 mi from city center
The price is $161 per night
$161
per night
May 23 - May 24
This hotel features a gym and an outdoor tennis court. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking. A 24-hour business center, free WiFi in public areas, and a terrace are also on offer.
Pet friendly
Breakfast included
Mountain Sports Inn

Mountain Sports Inn

2 out of 5
813 Killington Road, Killington, VT
7.89 mi from city center
The price is $94 per night
$94
per night
May 26 - May 27
A restaurant, free self parking, and a communal living room are among this hotel's amenities. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Luggage storage and concierge services are also provided.
Breakfast included
Parking included
Hampton Inn Rutland

Hampton Inn Rutland

2.5 out of 5
47 Farrell Rd, Rutland, VT
Free Cancellation
Reserve now, pay when you stay
15.18 mi from city center
The price is $127 per night
$127
per night
May 12 - May 13
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
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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.

Top hotels in Pittsfield for Extended Stay

Queen Studio on the 2nd floor with outdoor heated pool 207

Queen Studio on the 2nd floor with outdoor heated pool 207

Killington
The price is $104 per night from May 19 to May 20
$104
per night
May 19 - May 20
9.4/10 Exceptional! (3 reviews)
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.

Seize your some day

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.

Pittsfield hotels essential information

Accommodation
1,621 hotels
Lowest Price
$94
Highest Price
$289
Popular hotels
Comfort Inn Trolley Square, Killington Mountain Lodge, Tapestry Collection by Hilton, Days Inn by Wyndham Rutland/Killington Area, North Star Lodge and Resort, Woodstock Inn & Resort, The Mountain Inn at Killington, Best Western Inn & Suites Rutland-Killington, Mountain Sports Inn, Hampton Inn Rutland

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 $94. 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 1,621 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 Mountain Inn at Killington

The Mountain Inn at Killington

5 out of 5
Posted 4 days ago
Travelocity Verified Review
"The Ultimate Eastern United States Ski Experience! Majestic mountain views and steps from the slopes! That’s only some of the finer points of the luxurious and rustic Mountain Inn at Killington. Situated at 47 Old Mill Road in Killington, VT, this inn is a 1 minute car ride or short walk to the “Beast of the East” known as Killington. The walk is perhaps 5 minutes from door-to-chairlift at Ramshead Mountain—one of six peaks that compromise Killington ski resort, which looms in the distance from the grounds of the inn. The inn is cozy, quiet, clean, modern yet rustic, and dog-friendly. There’s lots to enjoy from the on-site whiskey distillery and restaurant (Still on the Mountain), the bar, and the breakfast nook which serves a generous array of morning pick-me-ups including scones, sweet rolls, fruit, cold cereal in individually packaged bowl containers, Chobani Greek yogurt, water, juice, coffee and tea. I took my dog with me on a ski trip and we stayed two nights in April. On property you will also find a gift shop, live music on Friday and Saturday nights, an outdoor heated pool (no dogs allowed) plus a small gym and game room with a pool table and corn hole set-up for indoor fun. There is no air conditioning, and my room got hot at times so to cool it off you may opt to shut off the heat and open a window. I did, and the mountain air cooled things off nicely. My room was beautifully designed with a walk-in shower with sliding glass door, two queen beds, wooden headboards!"
A verified traveler stayed at The Mountain Inn at Killington
The Mountain Inn at Killington

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