Pittsfield Holidays

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Pittsfield Holidays

From flight tickets to accommodation and every fantastic adventure in between, ebookers can make your ultimate Pittsfield break a reality.

You'd like your dinner served hot on a rooftop garden? Too easy. With over 500 airline partners and more than 500,000 worldwide properties to look through, the world is yours for the taking.

Looking for some peace of mind? Book a Flight + Hotel package through ebookers, and if you happen to spot a better deal elsewhere within 48 hours pre check in, we'll meet it and refund the difference. That's our Price Guarantee.

Whether you're seeking a sleepless city or the stillness of a coastal escape, we can help you satisfy your wanderlust. Terms and Conditions apply.

More Pittsfield hotels

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd Killington VT
The price is €198 per night
€198
12 Jan - 13 Jan 2026
includes taxes & fees
15.28 km from city centre
Our customers tell us that they can't get enough of the helpful staff at Killington Mountain Lodge, Tapestry Collection by Hilton. During your stay, you're just a quick walk from Killington Resort. Features include free WiFi in public areas and a free ski shuttle, plus a 24-hour gym.
Hot tub
Pet-friendly
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is €336 per night
€336
19 Jan - 20 Jan 2026
includes taxes & fees
28.87 km from city centre
Our customers tell us that they can't get enough of the helpful staff at Woodstock Inn & Resort. During your stay, you're just a quick walk from Middle Covered Bridge. Enjoy features like free WiFi in public areas and free valet parking, plus 4 restaurants. This property offers pet-friendly amenities, such as food and water bowls.
Pool
Hot tub
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd Killington VT
The price is €230 per night
€230
23 Dec - 24 Dec
includes taxes & fees
15.82 km from city centre
The free breakfast at The Mountain Inn at Killington gets high marks from our customers. During your stay, you're just a quick walk from Killington Resort. Free WiFi in public areas, free self-parking and a free ski shuttle are available.
Pool
Breakfast included
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
78 Weathervane Dr Killington VT
12.99 km from city centre
Our customers tell us that they can't get enough of the pool at North Star Lodge and Resort. During your stay, you'll be within walking distance of Killington Resort. Enjoy features like free WiFi in public areas and free self-parking, plus an outdoor pool.
Pool
Parking included
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St Rutland VT
The price is €135 per night
€135
4 Jan - 5 Jan 2026
includes taxes & fees
23.23 km from city centre
Our customers tell us that they enjoy the free breakfast at Comfort Inn Rutland - Killington. During your stay, you're just a quick walk from Vermont State Fairgrounds. You'll find features such as free WiFi in public areas and free self-parking, plus an indoor pool.
Pool
Hot tub
Mountain Sports Inn

Mountain Sports Inn

2 out of 5
813 Killington Road Killington VT
The price is €121 per night
€121
19 Jan - 20 Jan 2026
includes taxes & fees
12.71 km from city centre
Our customers tell us that they enjoy the free breakfast at Mountain Sports Inn. During your stay, you'll be within walking distance of Gifford Woods State Park. You'll find features such as free WiFi in public areas and free self-parking, plus a restaurant.
Breakfast included
Parking included
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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.

Cheap flights to Pittsfield

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, 31 Dec - Thu, 1 Jan
CLT
Charlotte
LEB
Lebanon
€405 Return, found 2 days ago
€405
Return
found 2 days ago
Select United flight, departing Wed, 31 Dec from Charlotte to Lebanon, returning Thu, 1 Jan, priced at €405 found 2 days ago
Thu, 1 Jan - Wed, 7 Jan
CLT
Charlotte
LEB
Lebanon
€430 Return, found 2 days ago
€430
Return
found 2 days ago
Select Delta flight, departing Thu, 1 Jan from Charlotte to Lebanon, returning Wed, 7 Jan, priced at €430 found 2 days ago
Wed, 31 Dec - Tue, 6 Jan
CLT
Charlotte
LEB
Lebanon
€442 Return, found 2 days ago
€442
Return
found 2 days ago
Select United flight, departing Wed, 31 Dec from Charlotte to Lebanon, returning Tue, 6 Jan, priced at €442 found 2 days ago
Thu, 1 Jan - Thu, 8 Jan
CLT
Charlotte
LEB
Lebanon
€456 Return, found 2 days ago
€456
Return
found 2 days ago
Select Delta flight, departing Thu, 1 Jan from Charlotte to Lebanon, returning Thu, 8 Jan, priced at €456 found 2 days ago
Wed, 31 Dec - Wed, 31 Dec
CLT
Charlotte
LEB
Lebanon
€465 Return, found 2 days ago
€465
Return
found 2 days ago
Select Delta flight, departing Wed, 31 Dec from Charlotte to Lebanon, returning Wed, 31 Dec, priced at €465 found 2 days ago
Wed, 31 Dec - Fri, 9 Jan
CLT
Charlotte
LEB
Lebanon
€468 Return, found 2 days ago
€468
Return
found 2 days ago
Select United flight, departing Wed, 31 Dec from Charlotte to Lebanon, returning Fri, 9 Jan, priced at €468 found 2 days ago

Other holiday destinations

^Savings based on all package bookings with Flight + Hotel made on ebookers.ie from as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.