Pittsfield Vacation Packages 2026 from $518

Pittsfield flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

The Inn at Buzzards Bay

Save 100% on your flight

$518

per person

Mar 18 - Mar 25

found 1 day ago

Roundtrip flight included

Denver (DEN) 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.

The Cove At Yarmouth

Save 100% on your flight

$624

per person

Mar 18 - Mar 25

found 1 day ago

Roundtrip flight included

Denver (DEN) to Boston (BOS)

A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free aparthotel. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.

Boston Harbor Hotel

North End

Save 100% on your flight

$1,735

per person

Apr 8 - Apr 12

found 23 hours ago

Roundtrip flight included

Denver (DEN) to Boston (BOS)

A marina, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the indoor pool and perks like free WiFi.

By the Sea Guests Bed & Breakfast & Suites

Save 100% on your flight

$1,007

per person

Mar 18 - Mar 25

found 1 day ago

Roundtrip flight included

Denver (DEN) to Boston (BOS)

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.

Raffles Boston

Back Bay

Save 100% on your flight

$2,220

per person

Apr 21 - Apr 25

found 1 day ago

Roundtrip flight included

Denver (DEN) to Boston (BOS)

A full-service spa, 3 restaurants, and an indoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and rooftop terrace.

Top Pittsfield hotels deals

Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

76 Mountain Rd Epsom NH

$141 nightly

$153 total

Feb 25 - Feb 26

Total with taxes and fees

This cabin includes express check-out and a virtual front desk. Take advantage of the free self parking.

Hampton Inn by Hilton Concord/Bow

515 South St Bow NH

Free Cancellation

Reserve now, pay when you stay

$106 nightly

$115 total

Feb 22 - Feb 23

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.

Comfort Inn Concord South End

71 Hall St Concord NH

Free Cancellation

Reserve now, pay when you stay

$111 nightly

$120 total

Feb 26 - Feb 27

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 continental breakfast and free self parking.

Pool

Breakfast included

Steele Hill Resorts

516 Steele Hill Road Sanbornton NH

$189 nightly

$205 total

Feb 12 - Feb 13

Total with taxes and fees

A golf course, a full-service spa, and 2 indoor pools are all featured at this hotel. Bring the family and enjoy the children's pool, waterslide, and playground. Enjoy the 2 outdoor tennis courts and perks like free self parking and free WiFi.

Pool

Hot Tub

Fireside Inn & Suites Gilford

17 Harris Shore Road Gilford NH

Free Cancellation

Reserve now, pay when you stay

$134 nightly

$146 total

Mar 1 - Mar 2

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free internet in public areas. Enjoy the seasonal outdoor pool and free perks like on-the-go breakfast and free self parking.

Winnisquam Lake Inn

788 Laconia Rd Tilton NH

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$97 total

Feb 12 - Feb 13

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.

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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.

Drake Field

After visiting Drake Field, make a plan to see the other sights and activities in Pittsfield.

Scenic Theatre

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

Frequently asked questions

How much are vacation packages to Pittsfield?

With Travelocity vacation packages, you could live it up in Pittsfield from just $518. 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.