Deals on vacations and trips to Pittsfield

Save when you book Pittsfield package deals

Choose two or more items and save on your trip:

Pittsfield flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Quality Inn & Conference Center

Quality Inn & Conference Center

2.5 out of 5
per person
Jul 18 - Jul 20
found 1 day ago
Roundtrip flight included
Charleston (CHS) to Franklin (FKL)
This hotel features a restaurant, a gym, and a bar/lounge. Free perks include buffet breakfast, free self parking, and a roundtrip airport shuttle. Free WiFi in public areas, a garden, and laundry facilities are also on offer.

Top Pittsfield hotels deals

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
$88 nightly
The price is $100 total per night
$100 total
Jun 1 - Jun 2
Total includes 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.
Pool
Breakfast included
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
$229 nightly
The price is $258 total per night
$258 total
Jun 4 - Jun 5
Total includes taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at one of the 2 bars/lounges and enjoy perks like free self parking.
Pool
Spa
Days Inn by Wyndham Warren

Days Inn by Wyndham Warren

3 out of 5
210 Ludlow Street, Warren, PA
Free Cancellation
Reserve now, pay when you stay
$70 nightly
The price is $77 total per night
$77 total
Jun 2 - Jun 3
Total includes taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and free perks like on-the-go breakfast and free self parking.
Pool
Breakfast included
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
$144 nightly
The price is $162 total per night
$162 total
Jun 8 - Jun 9
Total includes 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.
Pool
Parking included
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
$114 nightly
The price is $132 total per night
$132 total
Jun 8 - Jun 9
Total includes 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.
Pool
Breakfast included
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
Free Cancellation
Reserve now, pay when you stay
$126 nightly
The price is $142 total per night
$142 total
Jun 8 - Jun 9
Total includes taxes and fees
This resort features a golf course, ski-in/ski-out access, and a full-service spa. Take advantage of ski passes and ski storage on site. Bring the family and enjoy the mini golf, waterslide, and playground.
Pool
Hot Tub
Don't see what you're looking for?
See all available properties in Pittsfield
View all properties
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 $333. 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.

Photos of local treasures

Browse Pittsfield vacation photos for more inspiration