Pittsfield Vacation Packages 2026 from $727

Pittsfield flight + hotel vacation packages

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

Boston Lodge and Suites

Dorchester

Save 100% on your flight

$727

per person

Nov 25 - Nov 28

found 21 hours ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

Free WiFi in public areas, a terrace, and a garden are available at this hotel. Families will appreciate the playground, onsite laundry facilities, and in-room childcare. A hair salon, a picnic area, and express check-out are also on offer.

Boston Harbor Hotel

North End

Save 100% on your flight

$1,084

per person

Dec 16 - Dec 20

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) 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.

Raffles Boston

Back Bay

Save 100% on your flight

$1,307

per person

Dec 16 - Dec 20

found 16 hours ago

Roundtrip flight included

Atlanta (ATL) 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.

Four Seasons Hotel Boston

Bay Village

Save 100% on your flight

$1,399

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, laundry service, and valet parking. There's a 24-hour gym on site, and laundry facilities and concierge services are also offered.

Mandarin Oriental, Boston

Back Bay

Save 100% on your flight

$1,508

per person

Dec 16 - Dec 20

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Boston (BOS)

A full-service spa, a gym, and a restaurant are all featured at this smoke-free hotel. Families will appreciate the onsite laundry facilities and babysitting. Enjoy the sauna and perks like free WiFi.

Top Pittsfield hotels deals

The Centennial

96 Pleasant St Concord NH

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$138 total

Nov 4 - Nov 5

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 4 conference rooms, along with express check-out. A 24-hour gym and luggage storage are also provided.

Breakfast included

Pet friendly

Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

76 Mountain Rd Epsom NH

$175 nightly

$190 total

Nov 5 - Nov 6

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

Best Western Plus Landmark Inn

480 Main Street Laconia NH

Free Cancellation

Reserve now, pay when you stay

$101 nightly

$110 total

Nov 1 - Nov 2

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-out. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Breakfast included

Parking included

The Naswa Resort

1086 Weirs Blvd Laconia NH

$154 nightly

$167 total

Oct 8 - Oct 9

Total with taxes and fees

This smoke-free resort features a private beach and 2 restaurants. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas.

On private beach

Parking included

Hampton Inn by Hilton Concord/Bow

515 South St Bow NH

$101 nightly

$110 total

Nov 1 - Nov 2

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

Fireside Inn & Suites Gilford

17 Harris Shore Road Gilford NH

Free Cancellation

Reserve now, pay when you stay

$124 nightly

$135 total

Nov 1 - Nov 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.

Pool

Hot Tub

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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.

Stay near popular Pittsfield attractions

Harold Conrad Square

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

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Frequently asked questions

How much are vacation packages to Pittsfield?

With Travelocity vacation packages, you could live it up in Pittsfield from just $727. 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.