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 area home - 4-seasons & hot tub. Sleeps 12+

Killington area home - 4-seasons & hot tub. Sleeps 12+

1.53 km from city centre
During your stay at this holiday home, you're just a quick walk from Green Mountain National Forest. 1 hot tub and an arcade/games room are available. Enjoy your stay with amenities like free WiFi and a kitchen in the holiday home.
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 €155 per night
€155
includes taxes & fees
18 Nov - 19 Nov
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.
Comfort Inn Trolley Square

Comfort Inn Trolley Square

2.5 out of 5
19 Allen St, Rutland, VT
The price is €104 per night
€104
includes taxes & fees
26 Nov - 27 Nov
23.23 km from city centre
Our customers tell us that they enjoy the free breakfast at Comfort Inn Trolley Square. 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
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
The price is €113 per night
€113
includes taxes & fees
26 Nov - 27 Nov
24.29 km from city centre
Our customers tell us that they can't get enough of the helpful staff at Days Inn by Wyndham Rutland/Killington Area. During your stay, you're just a quick walk from Diamond Run Mall. You'll find features such as free breakfast, free WiFi in public areas and free self-parking.
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is €359 per night
€359
includes taxes & fees
1 Dec - 2 Dec
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 Red Wagon Toy Company. 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
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
78 Weathervane Dr, Killington, VT
The price is €109 per night
€109
includes taxes & fees
1 Dec - 2 Dec
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.
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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.

Thu, 19 Dec - Thu, 26 Dec
EWR
New York
LEB
Lebanon
€392 Return, found 20 hours ago
€392
Return
found 20 hours ago
Select United flight, departing Thu, 19 Dec from New York to Lebanon, returning Thu, 26 Dec, priced at €392 found 20 hours ago
Thu, 19 Dec - Thu, 26 Dec
EWR
New York
LEB
Lebanon
€401 Return, found 20 hours ago
€401
Return
found 20 hours ago
Select United flight, departing Thu, 19 Dec from New York to Lebanon, returning Thu, 26 Dec, priced at €401 found 20 hours ago
Thu, 19 Dec - Thu, 26 Dec
EWR
New York
LEB
Lebanon
€415 Return, found 20 hours ago
€415
Return
found 20 hours ago
Select United flight, departing Thu, 19 Dec from New York to Lebanon, returning Thu, 26 Dec, priced at €415 found 20 hours 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.