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Choose from 1582 Pittsfield Hotel Deals

Killington Mountain Lodge, Tapestry Collection by Hilton
Killington Mountain Lodge, Tapestry Collection by Hilton
3.5 out of 5
2617 Killington Rd, Killington, VT
  • 15 min walk from Killington Resort
The price is $170 per night from Dec 3 to Dec 4
$170
includes taxes & fees
Dec 3 - Dec 4
Stay at this 3.5-star ski hotel in Killington. Enjoy free WiFi, a free ski shuttle, and a 24-hour fitness center. Our guests praise the helpful staff and the ...
7.2/10 Good! (1,000 reviews)
"Great experience! It was a lot of fun around the pool table or the fire pit outside. We loved it! It was great to have our dog with us everywhere around the hotel. Everything is very clean and in modern design. The only downside was that the restaurant dinner menu is limited to 5 options and there ..."

Reviewed on Oct 29, 2024

Killington Mountain Lodge, Tapestry Collection by Hilton
Comfort Inn Trolley Square
Comfort Inn Trolley Square
2.5 out of 5
19 Allen St, Rutland, VT
  • 27 min drive from Killington Resort
The price is $114 per night from Dec 1 to Dec 2
$114
includes taxes & fees
Dec 1 - Dec 2
Book a stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8/10 Very Good! (1,001 reviews)
"Staff helpful and friendly. Rooms small, but space is used efficiently. Rooms were clean and welcoming. There is occasional noise from the mechanics of the building (e.g. HVAC). A bit outside of town, probably a 20 minute walk to city center. I was comfortable, felt safe, and would stay there again ..."

Reviewed on Nov 10, 2024

Comfort Inn Trolley Square
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
  • 28 min drive from Killington Resort
The price is $115 per night from Nov 17 to Nov 18
$115
includes taxes & fees
Nov 17 - Nov 18
Book a stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
6.2/10 (1,000 reviews)
"People are very, very hard-working and they’re working on improving their hotel. I was very impressed how they use the substance when cleaning to make sure the mirror in the bathroom did not fog up during showers. I know that’s not a big thing but it is when you’re in a hurry to get ready and go. ..."

Reviewed on Nov 3, 2024

Days Inn by Wyndham Rutland/Killington Area
Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 out of 5
Fourteen The Green, Woodstock, VT
  • 43 min drive from Killington Resort
The price is $384 per night from Dec 1 to Dec 2
$384
includes taxes & fees
Dec 1 - Dec 2
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (480 reviews)
"Lovely hotel. Could do with some updates in areas but a very unique picturesque place ."

Reviewed on Nov 8, 2024

Woodstock Inn & Resort
North Star Lodge and Resort
North Star Lodge and Resort
2 out of 5
78 Weathervane Dr, Killington, VT
  • 5 min drive from Killington Resort
The price is $118 per night from Dec 1 to Dec 2
$118
includes taxes & fees
Dec 1 - Dec 2
Book a stay at this family-friendly hotel in Killington. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the pool and the helpful staff ...
8.4/10 Very Good! (991 reviews)
Would stay again!
"I have no complaints about our stay, the hotel room was clean and the bed was comfortable. The Establishment is a bit outdated but if that doesn't bother you, this was a great place to stay. The staff I interacted with were both helpful and friendly."

Reviewed on Nov 8, 2024

North Star Lodge and Resort
My Place Hotel-Randolph VT
My Place Hotel-Randolph VT
2 out of 5
2440 Vermont 66, Randolph Center, VT
  • 1 hour drive from Killington Resort
The price is $137 per night from Dec 8 to Dec 9
$137
includes taxes & fees
Dec 8 - Dec 9
Book a stay at this business-friendly hotel in Randolph Center. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Whale Dance Sculpture ...
9.2/10 Wonderful! (74 reviews)
"Stayed while passing through on my drive to Boston. Hotel and rooms are super clean and comfortable. Bed was super comfortable which is not always the case in hotels. There was also a kitchenette and full size fridge in the room which is always a convenient thing. Woud stay again here without ..."

Reviewed on Nov 15, 2024

My 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
  • 5 min walk from Killington Resort
The price is $161 per night from Nov 17 to Nov 18
$161
includes taxes & fees
Nov 17 - Nov 18
Book a stay at this ski hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
9/10 Wonderful! (703 reviews)
Great stay
"Clean, super friendly staff and great location. Restaurant was closed but it’s stick season."

Reviewed on Nov 14, 2024

The Mountain Inn at Killington
The Shire Woodstock
The Shire Woodstock
3 out of 5
46 Pleasant St., Woodstock, VT
  • 45 min drive from Killington Resort
The price is $192 per night from Nov 17 to Nov 18
$192
includes taxes & fees
Nov 17 - Nov 18
Stay at this 3-star hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in ...
8.6/10 Excellent! (675 reviews)
"Lovely place sitting in a the very lovely town of Woodstock. Town is walkable and there is a grocery store across the street from the hotel. The room was very nice, King bed and a big window view out back of the river and mountains beyond. Staff is very nice and accommodating. There's a fridge in ..."

Reviewed on Nov 10, 2024

The Shire Woodstock
Best Western Inn & Suites Rutland-Killington
Best Western Inn & Suites Rutland-Killington
2.5 out of 5
5 Best Western Place, Rutland, VT
  • 22 min drive from Killington Resort
The price is $177 per night from Nov 24 to Nov 25
$177
includes taxes & fees
Nov 24 - Nov 25
Stay at this hotel in Rutland. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.6/10 Excellent! (997 reviews)
"Nice hotel. Small front desk check-in issue but they resolved it."

Reviewed on Nov 10, 2024

Best Western Inn & Suites Rutland-Killington
Mountain Sports Inn
Mountain Sports Inn
2 out of 5
813 Killington Road, Killington, VT
  • 5 min drive from Killington Resort
The price is $98 per night from Nov 17 to Nov 18
$98
includes taxes & fees
Nov 17 - Nov 18
Stay at this hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
8.6/10 Excellent! (801 reviews)
"Good one"

Reviewed on Oct 28, 2024

Mountain Sports Inn
Brandon Inn
Brandon Inn
3 out of 5
20 Park Street, Brandon, VT
  • 55 min drive from Killington Resort
The price is $143 per night from Nov 17 to Nov 18
$143
includes taxes & fees
Nov 17 - Nov 18
Stay at this 3-star hotel in Brandon. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.6/10 Excellent! (386 reviews)
"I liked the charm of the building and the staff was very friendly"

Reviewed on Nov 11, 2024

Brandon Inn
Hampton Inn Rutland
Hampton Inn Rutland
2.5 out of 5
47 Farrell Rd, Rutland, VT
  • 28 min drive from Killington Resort
The price is $158 per night from Nov 17 to Nov 18
$158
includes taxes & fees
Nov 17 - Nov 18
Book a stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (854 reviews)
"Quick and clean"

Reviewed on Nov 8, 2024

Hampton Inn Rutland
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.

HOTW-Hotel-Deals-726-959@2x.jpg (1918×258)*Savings based on Hot Rate® hotel bookings as compared with the lowest published rates found on leading retail travel sites. Hot Rates are different from retail rates. With Hot Rates you enter the date, location and star rating. Hotel revealed only after booking. All bookings final.

Find cheap hotels in Pittsfield

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If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $98. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get up to 60% Pittsfield hotel deals at the last minute.

While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in Pittsfield. No matter your reason for visiting Pittsfield, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.

Frequently Asked Questions About Pittsfield hotels

Where can I find the best last-minute travel deals?

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How many hotels are there in Pittsfield?

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How to find cheap car rentals in Pittsfield?

Finding a cheap car rental deal in Pittsfield is as easy as scoring cheap hotels in Pittsfield. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can even save up to 60% off a car rental deal if you book a Hotwire Hot Rate at the last minute.

Is it safe to travel to Pittsfield now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Pittsfield right now?” When it’s time to book your getaway, be sure to check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.