Pittsfield Vacation Packages 2026 from $1,072

Pittsfield flight + hotel vacation packages

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

Fairmont Copley Plaza, Boston

Back Bay

Save 100% on your flight

$1,072

per person

Jul 25 - Jul 30

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. There's a rooftop terrace on site, and laundry facilities and concierge services are also offered.

Boston Harbor Hotel

North End

Save 100% on your flight

$1,779

per person

Jul 25 - Jul 30

found 1 day ago

Roundtrip 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.

By the Sea Guests Bed & Breakfast & Suites

$1,174

per person

Aug 2 - Aug 7

found 1 day ago

Roundtrip flight included

Charlotte (CLT) 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.

Nantucket Inn

Save 100% on your flight

$2,024

per person

Aug 2 - Aug 7

found 1 day ago

Roundtrip flight included

Charlotte (CLT) to Boston (BOS)

2 outdoor tennis courts, 2 hot tubs, and an indoor pool are all featured at this smoke-free resort. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy a meal from the restaurant and perks like free self parking and a free beach shuttle.

Chatham Tides

Save 100% on your flight

$2,647

per person

Jul 25 - Aug 1

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Boston (BOS)

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, a picnic area, and a computer station are also on offer.

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.

Kitchen

Outdoor Space

Steele Hill Resorts

516 Steele Hill Road Sanbornton NH

$189 nightly

$205 total

May 26 - May 27

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

Hampton Inn by Hilton Concord/Bow

515 South St Bow NH

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$106 total

May 31 - Jun 1

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

DoubleTree by Hilton Downtown Concord

172 N Main St Concord NH

Free Cancellation

Reserve now, pay when you stay

$158 nightly

$172 total

Jun 7 - Jun 8

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Pool

Pet friendly

Winnisquam Lake Inn

788 Laconia Rd Tilton NH

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$97 total

May 26 - May 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.

Breakfast included

Parking included

Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

76 Mountain Rd Epsom NH

$175 nightly

$190 total

Jun 24 - Jun 25

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

Don't see what you're looking for?

See all available properties in Pittsfield

View all properties

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 $1,072. 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.