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'll be close to White River Golf Club. 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.
Hot tub
Kitchen
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 €126 per night
€126
per night
30 Jun - 1 Jul
15.28 km from city centre
During your stay at Killington Mountain Lodge, Tapestry Collection by Hilton, 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
Comfort Inn Trolley Square

Comfort Inn Trolley Square

2.5 out of 5
19 Allen St, Rutland, VT
The price is €136 per night
€136
per night
17 Jun - 18 Jun
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
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is €441 per night
€441
per night
17 Jun - 18 Jun
28.87 km from city centre
Our customers tell us they enjoy Woodstock Inn & Resort's good location. 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
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 €114 per night
€114
per night
17 Jun - 18 Jun
24.29 km from city centre
Our customers tell us that they enjoy 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.
Breakfast included
Pet-friendly
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd, Killington, VT
The price is €135 per night
€135
per night
20 Jun - 21 Jun
15.82 km from city centre
Our customers tell us that they enjoy the free breakfast at The Mountain Inn at Killington. 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
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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.

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.