Deals on vacations and trips to Pittsfield

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Pittsfield flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Webb's Year Round Resort

Webb's Year Round Resort

2.5 out of 5
Price was $611, price is now $572 per person
$572
per person
May 22 - May 25
found 7 hours ago
Roundtrip non-stop flight included
Orlando (ORL) to Jamestown (JHW)
This motel features an indoor pool and a hot tub. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A lobby fireplace, a computer station, and laundry facilities are also on offer.
The Spencer Hotel & Spa

The Spencer Hotel & Spa

2.5 out of 5
Price was $859, price is now $758 per person
$758
per person
May 22 - May 25
found 7 hours ago
Roundtrip non-stop flight included
Orlando (ORL) to Jamestown (JHW)
This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free cooked-to-order breakfast each morning. A business center, a terrace, and a garden are also on offer.
Athenaeum Hotel

Athenaeum Hotel

3.5 out of 5
Price was $805, price is now $759 per person
$759
per person
May 22 - May 25
found 7 hours ago
Roundtrip non-stop flight included
Orlando (ORL) to Jamestown (JHW)
A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A garden, a lobby fireplace, and luggage storage are also on offer.

Top Pittsfield hotels deals

Charming Farmhouse on a working farm.

Charming Farmhouse on a working farm.

Pittsfield PA
$160 nightly
The price is $177 total per night
$177 total
Apr 21 - Apr 22
Total with taxes and fees
This farm stay includes a garden and laundry facilities.
La Quinta Inn & Suites by Wyndham Jamestown

La Quinta Inn & Suites by Wyndham Jamestown

3 out of 5
200 W 3rd St Jamestown NY
Free Cancellation
Reserve now, pay when you stay
$86 nightly
The price is $97 total per night
$97 total
Apr 21 - Apr 22
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.
Chautauqua Harbor Hotel - Jamestown

Chautauqua Harbor Hotel - Jamestown

3.5 out of 5
10 Dunham Ave Celoron NY
Free Cancellation
Reserve now, pay when you stay
$118 nightly
The price is $134 total per night
$134 total
Apr 23 - Apr 24
Total with taxes and fees
The hotel's indoor pool, gym, and 2 bars/lounges are among the featured amenities. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy a meal from the a restaurant and perks like free self parking.
DoubleTree by Hilton Jamestown

DoubleTree by Hilton Jamestown

4 out of 5
150 W 4th St Jamestown NY
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $110 total per night
$110 total
Apr 26 - Apr 27
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.
Peek'n Peak Resort Trademark Collection by Wyndham

Peek'n Peak Resort Trademark Collection by Wyndham

3.5 out of 5
1405 Olde Road Clymer NY
$125 nightly
The price is $141 total per night
$141 total
May 1 - May 2
Total with taxes and fees
This smoke-free resort features a golf course, a full-service spa, and 6 restaurants. Take advantage of ski lessons, ski rentals and ski passes on site, and enjoy downhill skiing. Bring the family and enjoy the mini golf, waterslide, and playground.
Holiday Inn Express & Suites Jamestown by IHG

Holiday Inn Express & Suites Jamestown by IHG

2.5 out of 5
2811 North Main Street Jamestown NY
Free Cancellation
$105 nightly
The price is $119 total per night
$119 total
Apr 23 - Apr 24
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 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.

Frequently asked questions

How much are vacation packages to Pittsfield?
Vacation packages, including flights and hotels in Pittsfield, start from as low as $572. Make your travel dreams come true and secure your dream vacation with Travelocity today.
Where can I get the best vacation package deals for Pittsfield?
There's no need to look any further than Travelocity. With no less than 400 air carriers and 1,000,000 properties worldwide, it's a piece of cake to put together a Pittsfield package deal that suits your travel style.
Why should I book my Pittsfield vacation bundle via Travelocity?
We take the hassle out of travel planning. Whether you're looking for a new destination to discover or want to make sure you get the best price on offer, we're here to assist. Our 24/7 customer support, quality service and Price Match Guarantee mean you can book with confidence with Travelocity.
Will I save money on my Pittsfield car rental if I book it with hotels and flights?
Bundling your hotel, flight and car into a Pittsfield vacation package is the easiest way to land the best prices. Plus, having your own set of wheels gives you the freedom to get to all those amazing sights you're itching to check out. Sitting 80 mi away from Pittsfield, Geneva State Park is one attraction that should feature on your itinerary. Top up the tank and make a day trip of it.
Which airport is best for Pittsfield?
Erie Intl. Airport (ERI) is one of the biggest airports in Pittsfield. It's around 45 mi northwest of the bustling downtown area. Other options available to you are Venango Regional Airport (FKL) (40 mi away from central Pittsfield) and Chautauqua County Airport (JHW) (25 mi away from central Pittsfield).
Where should I stay when visiting Pittsfield?
Many travelers choose to stay at the Charming Farmhouse on a working farm.. It's an excellent base for your Pittsfield escape.

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