Pittsfield Vacation Packages 2026 from $1,233

Pittsfield flight + hotel vacation packages

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

The Coach House

Save 100% on your flight

$1,233

per person

Sep 5 - Sep 8

found 8 hours ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

This hotel features free self parking and free WiFi in public areas. Enjoy the free on-the-go breakfast each morning.

The Atlas Hotel

Allston

Save 100% on your flight

$1,344

per person

Sep 23 - Sep 30

found 5 hours ago

Roundtrip flight included

Dallas (DAL) to Boston (BOS)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the laundry service and valet parking. A communal living room, luggage storage, and concierge services are also on offer.

Iris Hotel Boston

Coolidge Corner

Save 100% on your flight

$1,501

per person

Sep 23 - Sep 30

found 5 hours ago

Roundtrip flight included

Dallas (DAL) 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 computer station, dry cleaning, and luggage storage are also on offer.

Furnished Apartment Near Longwood

North Brookline

Save 100% on your flight

$1,808

per person

Sep 23 - Sep 30

found 5 hours ago

Roundtrip flight included

Dallas (DAL) to Boston (BOS)

This apartment features a virtual front desk. Take advantage of the self parking.

Mandarin Oriental, Boston

Back Bay

Save 100% on your flight

$1,266

per person

Sep 5 - Sep 8

found 22 hours ago

Roundtrip flight included

Chicago (ORD) 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

Bower Cabin- Cabin in woods on a remote pond, Romantic getaway, Green living!

Pittsfield NH

Get rates

This cabin includes a garden and barbecue grills.

Best Western Plus Landmark Inn

480 Main Street Laconia NH

Free Cancellation

Reserve now, pay when you stay

$116 nightly

$126 total

Jul 21 - Jul 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

The Naswa Resort

1086 Weirs Blvd Laconia NH

$179 nightly

$194 total

Jul 7 - Jul 8

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.

The Lake Estate on Winnisquam

725 Laconia Road Tilton NH

$324 nightly

$351 total

Jul 7 - Jul 8

Total with taxes and fees

This luxury hotel features a private beach, a full-service spa, and 2 restaurants. Traveling on business? Take advantage of the free WiFi in public areas and valet parking. Relax with a drink at one of the 2 bars/lounges and enjoy perks like free self parking.

On private beach

Pool

Winnisquam Lake Inn

788 Laconia Rd Tilton NH

Free Cancellation

Reserve now, pay when you stay

$109 nightly

$118 total

Jul 26 - Jul 27

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.

Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

76 Mountain Rd Epsom NH

$175 nightly

$190 total

Aug 4 - Aug 5

Total with taxes and fees

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

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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 $1,233. 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.