Pittsfield Vacation Packages 2026 from $597

Pittsfield flight + hotel vacation packages

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

The Charles Hotel

West Cambridge

$597

per person

Mar 20 - Mar 22

found 14 hours ago

Roundtrip non-stop flight included

Cleveland (CLE) to Boston (BOS)

A full-service spa, 3 restaurants, and a 24-hour gym are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Self parking, limo/town car service, and a snack bar/deli are also offered.

The Langham, Boston

Downtown Boston

Save 100% on your flight

$1,215

per person

May 15 - May 18

found 1 day ago

Roundtrip flight included

Nashville (BNA) to Boston (BOS)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the 24-hour gym and perks like free WiFi.

Raffles Boston

Back Bay

Save 100% on your flight

$2,237

per person

May 15 - May 18

found 1 day ago

Roundtrip flight included

Cleveland (CLE) 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.

Omni Parker House

Downtown Boston

Save 100% on your flight

$770

per person

May 15 - May 18

found 1 day ago

Roundtrip flight included

Nashville (BNA) to Boston (BOS)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A coffee shop, express check-out, and a computer station are also on offer.

Found Hotel Boston Common

Bay Village

Save 100% on your flight

$745

per person

May 15 - May 18

found 1 day ago

Roundtrip flight included

Nashville (BNA) to Boston (BOS)

Free WiFi in public areas, luggage storage, and a safe deposit box are available at this hotel. There's locker space and multilingual staff can provide around-the-clock assistance.

Top Pittsfield hotels deals

The Centennial

96 Pleasant St Concord NH

Free Cancellation

Reserve now, pay when you stay

$153 nightly

$166 total

Feb 22 - Feb 23

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

Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

76 Mountain Rd Epsom NH

$141 nightly

$153 total

Feb 23 - Feb 24

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

Hampton Inn by Hilton Concord/Bow

515 South St Bow NH

Free Cancellation

Reserve now, pay when you stay

$106 nightly

$115 total

Feb 23 - Feb 24

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

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

Mar 1 - Mar 2

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

Tru by Hilton Concord

South Main Street, 406 Concord NH

Free Cancellation

Reserve now, pay when you stay

$114 nightly

$124 total

Feb 26 - Feb 27

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

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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.

Pittsfield Town Hall

After visiting Pittsfield Town Hall, 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.

Frequently asked questions

How much are vacation packages to Pittsfield?

With Travelocity vacation packages, you could live it up in Pittsfield from just $597. 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.