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.
Hinckleys Dreamwood Cottages

Hinckleys Dreamwood Cottages

3 out of 5
Save 100% on your flight
Price was $1,165, price is now $873 per person
$873
per person
Oct 19 - Oct 23
found 23 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Bangor (BGR)
Free WiFi in public areas is available at this cottage. Take advantage of the free self parking.
3Bedroom2Bath CarriageHouse Pet Friendly

3Bedroom2Bath CarriageHouse Pet Friendly

3.5 out of 5
Save 100% on your flight
Price was $2,057, price is now $1,248 per person
$1,248
per person
Oct 19 - Oct 23
found 23 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Bangor (BGR)
This vacation home includes a garden and barbecue grills. Take advantage of the free self parking.
3BedroomApt Pool CampFire PlayArea

3BedroomApt Pool CampFire PlayArea

3 out of 5
Save 100% on your flight
Price was $1,933, price is now $1,303 per person
$1,303
per person
Oct 19 - Oct 23
found 23 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Bangor (BGR)
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this apartment. A garden is also provided.
Bar Harbor Main Street Apartments

Bar Harbor Main Street Apartments

3.5 out of 5
Downtown Bar Harbor
Save 100% on your flight
Price was $3,092, price is now $2,187 per person
$2,187
per person
Sep 24 - Sep 29
found 9 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Bangor (BGR)
The apartment doesn't skimp on freebies - guests receive free continental breakfast and free self parking.
Whitehall

Whitehall

3 out of 5
Price was $1,193, price is now $901 per person
$901
per person
Oct 20 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Bangor (BGR)
A bar/lounge and a terrace are featured at this hotel, along with free self parking. Guests will appreciate free perks like self-serve breakfast and WiFi in public areas. A garden, express check-out, and luggage storage are also on offer.

Top Pittsfield hotels deals

Family, Friends and Fun for all

Family, Friends and Fun for all

2 out of 5
$357 nightly
The price is $389 total per night
$389 total
Aug 24 - Aug 25
Total includes taxes and fees
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Angel Mist Retreat Garage Apartment

Angel Mist Retreat Garage Apartment

$284 nightly
The price is $310 total per night
$310 total
Aug 25 - Aug 26
Total includes taxes and fees
This condo features free WiFi in public areas, a garden, and laundry facilities.
Kitchen
Washer
Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville

2 out of 5
376 Main Street, Waterville, ME
Free Cancellation
Reserve now, pay when you stay
$146 nightly
The price is $159 total per night
$159 total
Aug 24 - Aug 25
Total includes taxes and fees
This hotel features a hot tub, a gym, and a restaurant. Enjoy the seasonal outdoor pool and free perks like continental breakfast and free self parking. Free parking, a business center, and free WiFi in public areas are also offered.
Pool
Hot Tub
The Elmwood

The Elmwood

2.5 out of 5
455 Kennedy Memorial Dr, Waterville, ME
Free Cancellation
Reserve now, pay when you stay
$149 nightly
The price is $162 total per night
$162 total
Aug 20 - Aug 21
Total includes taxes and fees
This motel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.
Breakfast included
Pet friendly
Holiday Inn Express & Suites Waterville - North by IHG

Holiday Inn Express & Suites Waterville - North by IHG

2.5 out of 5
332 Main St, Waterville, ME
Free Cancellation
$135 nightly
The price is $147 total per night
$147 total
Sep 4 - Sep 5
Total includes taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Best Western Plus Waterville Grand Hotel

Best Western Plus Waterville Grand Hotel

3 out of 5
375 Main Street, Waterville, ME
Free Cancellation
Reserve now, pay when you stay
$140 nightly
The price is $153 total per night
$153 total
Aug 24 - Aug 25
Total includes taxes and fees
This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Pool
Pet friendly
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.

Popular places to visit

Northern Light Sebasticook Valley Hospital

Though Northern Light Sebasticook Valley Hospital might be what brings you to town, perhaps you'll have a chance to explore more of Pittsfield while you are here.

Northern Light Sebasticook Valley Hospital

JW Parks Golf Course

Enjoy a round of golf in Pittsfield at JW Parks Golf Course. Make some time to visit the shops while you're in the area.

JW Parks Golf Course

Frequently asked questions

How much are vacation packages to Pittsfield?
Travelocity offers great package deals to Pittsfield, as well as flights and hotels, starting from an impressive $873. With all that extra cash, you could purchase some cool tours or maybe even tack on a few extra days to your exciting adventure.
Where can I get the best vacation package deals for Pittsfield?
Travelocity can help you snag an awesome Pittsfield package deal. With as many as 400 air carriers and 1,000,000 properties worldwide, we're sure you'll be able to craft the perfect itinerary.
Why should I book my Pittsfield vacation bundle with Travelocity?
From our 24/7 customer support to our range of amazing destinations, we're dedicated to giving you the most unforgettable escape. All you have to do is to click and book — our Price Match Guarantee will make sure you get the best price.
Can I save money on my Pittsfield car rental if I bundle it with a hotel or flight?
With a Pittsfield vacation package, you can combine your flight, car and hotel bookings and save a tidy sum. If you want to uncover the best of this wonderful area, why not make tracks to Franconia Notch State Park? This must-see sight is 120 mi from Pittsfield. With a rental car, you'll be there in a flash.
Which airport is best for Pittsfield?
Bangor Intl. Airport (BGR) (30 mi away from the downtown area), Hancock County - Bar Harbor Airport (BHB) (55 mi away from central Pittsfield) and Knox County Regional Airport (RKD) (50 mi away from central Pittsfield) are all great options for Pittsfield.
Where should I stay when visiting Pittsfield?
The The OverNight Library ~ 1/2 mile off I-95 is popular with many visitors. Book soon before it's too late.

Photos of local treasures

Browse Pittsfield vacation photos for more inspiration