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.
The Hotel Salem

The Hotel Salem

3 out of 5
Downtown Salem
Save 100% on your flight
Price was $705, price is now $489 per person
$489
per person
Feb 1 - Feb 7
found 5 hours ago
Roundtrip flight included
Philadelphia (PHL) to Boston (BOS)
This hotel features a restaurant, a rooftop terrace, and a bar/lounge. WiFi in public areas is free. A terrace, luggage storage, and concierge services are also on offer.
The Hotel Portsmouth

The Hotel Portsmouth

3 out of 5
Downtown
Save 100% on your flight
Price was $843, price is now $574 per person
$574
per person
Feb 26 - Mar 4
found 16 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 4 onsite conference rooms. A snack bar/deli and concierge services are also provided.
The McKernan Inn

The McKernan Inn

3 out of 5
Price was $732, price is now $510 per person
$510
per person
Mar 20 - Mar 24
found 15 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
This inn features free WiFi in public areas, concierge services, and free self parking. Enjoy the free continental breakfast each morning. A garden, a picnic area, and luggage storage are also on offer.
AC Hotel by Marriott Portsmouth

AC Hotel by Marriott Portsmouth

3.5 out of 5
North End
Save 100% on your flight
Price was $840, price is now $599 per person
$599
per person
Feb 26 - Mar 4
found 16 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
This hotel features 2 bars/lounges and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. A restaurant, a 24-hour front desk, and dry cleaning are also provided.
The Inn at Buzzards Bay

The Inn at Buzzards Bay

2.5 out of 5
Price was $903, price is now $669 per person
$669
per person
Mar 7 - Mar 14
found 10 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Boston (BOS)
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A picnic area, express check-out, and barbecue grills are also on offer.

Top Pittsfield hotels deals

Hampton Inn by Hilton Concord/Bow

Hampton Inn by Hilton Concord/Bow

2.5 out of 5
515 South St Bow NH
Free Cancellation
Reserve now, pay when you stay
$102 nightly
The price is $110 total per night
$110 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

2 out of 5
76 Mountain Rd Epsom NH
$149 nightly
The price is $162 total per night
$162 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This cabin includes express check-out and a virtual front desk. Take advantage of the free self parking.
Kitchen
Pet friendly
Tru by Hilton Concord

Tru by Hilton Concord

2.5 out of 5
South Main Street, 406 Concord NH
Free Cancellation
Reserve now, pay when you stay
$106 nightly
The price is $115 total per night
$115 total
Dec 31 - Jan 1, 2026
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls and litter boxes. A 24-hour gym and a safe deposit box are also provided.
Breakfast included
Pet friendly
Winnisquam Lake Inn

Winnisquam Lake Inn

3 out of 5
788 Laconia Rd Tilton NH
Free Cancellation
Reserve now, pay when you stay
$85 nightly
The price is $92 total per night
$92 total
Dec 28 - Dec 29
Total with taxes and fees
This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free continental breakfast each morning. A terrace, a library, and a picnic area are also on offer.
Breakfast included
Parking included
The Centennial

The Centennial

4 out of 5
96 Pleasant St Concord NH
Free Cancellation
Reserve now, pay when you stay
$154 nightly
The price is $168 total per night
$168 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 4 conference rooms, free WiFi in public areas, and express check-out. Guests will appreciate freebies like continental breakfast and free self parking.
Breakfast included
Pet friendly
Best Western Plus Landmark Inn

Best Western Plus Landmark Inn

2.5 out of 5
480 Main Street Laconia NH
Free Cancellation
Reserve now, pay when you stay
$105 nightly
The price is $114 total per night
$114 total
Dec 28 - Dec 29
Total with taxes and fees
This hotel features an indoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
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.

Popular places to visit

Harold Conrad Square

After visiting Harold Conrad Square, make a plan to see the other sights and activities in Pittsfield.

Harold Conrad Square

Josiah Carpenter Library

Josiah Carpenter Library is just one of the places to see in Pittsfield, so why not enjoy the other things to explore during your travels?

Josiah Carpenter Library

Scenic Theatre

You can enjoy a show at Scenic Theatre on your trip to Pittsfield.

Scenic Theatre

Frequently asked questions

How much are vacation packages to Pittsfield?
With Travelocity vacation packages, you could live it up in Pittsfield from just $489. Activities, flights and hotels — we've got you. You'll save loads just for bundling together your bookings. And with everything taken care of before you go, you can sit back, relax and enjoy the adventure.
Where can I get the best vacation package deals for Pittsfield?
You can lock in awesome Pittsfield package deals with Travelocity. Select from as many as 400 air carriers and 1,000,000 worldwide properties and turn those travel fantasies into reality.
Why should I book my Pittsfield vacation package with Travelocity?
The three S's — savings, support and a stress-free booking — are just the tip of the iceberg. Enjoy a fulfilling travel experience knowing you can rely on our expert team of customer support professionals 24/7. With the Travelocity Price Match Guarantee, you know you'll always get the best deal available.
Will I save money on my Pittsfield car rental if I bundle it with a hotel or flight?
Combining your car, hotel and flight into a Pittsfield vacation package is a great way to land the best prices. Plus, having your own wheels gives you absolute freedom to make your way to all the landmarks you can't wait to see. Situated 65 mi from Pittsfield, Fenway Park is one place that should be on your must-do list. Fill up the tank and make a day trip of it.
Which airport is best for Pittsfield?
Portland Intl. Jetport Airport (PWM) is one of the most popular airports in Pittsfield. It's situated 55 mi northeast of the bustling downtown area. Your other choices are Manchester-Boston Regional Airport (MHT) (25 mi away from central Pittsfield) and Lebanon Municipal Airport (LEB) (55 mi away from central Pittsfield).
Where should I stay when visiting Pittsfield?
The Vasha is a cozy pet-friendly lake house for relaxing in a secluded location. is the first choice of many travelers. Book now to avoid missing out.

Photos of local treasures

Browse Pittsfield vacation photos for more inspiration