Pittsfield Vacation Packages 2026 from $520

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

$520

per person

Nov 13 - Nov 16

found 1 day ago

Roundtrip non-stop flight included

Pittsburgh (PIT) 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

$780

per person

Nov 6 - Nov 9

found 1 day 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.

Attitash Mountain Village

$621

per person

Sep 29 - Oct 2

found 11 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Manchester (MHT)

2 outdoor pools, 4 outdoor tennis courts, and an indoor pool are all featured at this smoke-free aparthotel. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site. Enjoy the sauna and perks like free self parking and free WiFi.

The Wylie Inn and Conference Center at Endicott College

Save 100% on your flight

$918

per person

Oct 28 - Nov 1

found 1 day ago

Roundtrip flight included

Denver (DEN) to Boston (BOS)

A 24-hour gym, free self parking, and wedding services are featured at this hotel. WiFi in public areas is free. A coffee shop, a computer station, and luggage storage are also on offer.

Mandarin Oriental, Boston

Back Bay

Save 100% on your flight

$1,030

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Denver (DEN) 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

Best Western Plus Landmark Inn

480 Main Street Laconia NH

Free Cancellation

Reserve now, pay when you stay

$114 nightly

$124 total

Sep 21 - Sep 22

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

Winnisquam Lake Inn

788 Laconia Rd Tilton NH

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$97 total

Aug 24 - Aug 25

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 Naswa Resort

1086 Weirs Blvd Laconia NH

$169 nightly

$183 total

Aug 30 - Aug 31

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

The Centennial

96 Pleasant St Concord NH

Free Cancellation

Reserve now, pay when you stay

$120 nightly

$130 total

Sep 10 - Sep 11

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

$179 nightly

$194 total

Aug 31 - Sep 1

Total with taxes and fees

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

Steele Hill Resorts

516 Steele Hill Road Sanbornton NH

$189 nightly

$205 total

Sep 1 - Sep 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

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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

Drake Field

After visiting Drake Field, 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 $520. 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.