Pittsfield Vacations 2026 from CA $1,350

Pittsfield flight + hotel packages

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

The Langham, Boston

Downtown Boston

CA $1,350

per person

Dec 19 - Dec 22

found 24 hours ago

Roundtrip flight included

Ottawa (YOW) to Boston (BOS)

Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Boston Harbor and Boston Common are located nearby.

Boston Harbor Hotel

North End

Save 100% on your flight

CA $1,856

per person

Dec 3 - Dec 7

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Boston (BOS)

Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions Boston Harbor and Boston Common are located nearby.

Four Seasons Hotel Boston

Bay Village

Save 100% on your flight

CA $1,856

per person

Nov 4 - Nov 7

found 23 hours ago

Roundtrip flight included

Detroit (DTW) to Boston (BOS)

Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the room service in our reviews. Popular attractions Boston Common and Copley Square are located nearby.

Mandarin Oriental, Boston

Back Bay

Save 100% on your flight

CA $1,689

per person

Nov 4 - Nov 7

found 23 hours ago

Roundtrip flight included

Detroit (DTW) to Boston (BOS)

Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions Copley Square and Fenway Park are located nearby.

Raffles Boston

Back Bay

Save 100% on your flight

CA $1,367

per person

Dec 25 - Dec 28

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.

Top Pittsfield hotels deals

Best Western Plus Landmark Inn

480 Main Street Laconia NH

Free cancellation

Reserve now, pay when you stay

CA $155

CA $168 total

Oct 22 - Oct 23

includes taxes & fees

Book a stay at this business-friendly hotel in Laconia. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Belknap Mill Society Museum and Sun Day's Salon & Spa, Inc. are located nearby.

Breakfast included

Parking included

Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

76 Mountain Rd Epsom NH

CA $191

CA $269 total

Oct 28 - Oct 29

includes taxes & fees

Stay at this cabin in Epsom. Enjoy free parking, patios, and climate control. Popular attractions James Park and Epsom Public Library are located nearby.

Kitchen

Pet-friendly

Fireside Inn & Suites Gilford

17 Harris Shore Road Gilford NH

Free cancellation

Reserve now, pay when you stay

CA $205

CA $222 total

Oct 26 - Oct 27

includes taxes & fees

Book a stay at this business-friendly hotel in Gilford. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Lake Winnipesaukee and Bank of New Hampshire Pavilion at Meadowbrook are located nearby.

Pool

Hot tub

Hampton Inn by Hilton Concord/Bow

515 South St Bow NH

Free cancellation

Reserve now, pay when you stay

CA $138

CA $150 total

Oct 25 - Oct 26

includes taxes & fees

Book a stay at this business-friendly hotel in Bow. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Capitol Center for the Arts and Plausawa Valley Country Club are located nearby.

Pool

Breakfast included

Winnisquam Lake Inn

788 Laconia Rd Tilton NH

Free cancellation

Reserve now, pay when you stay

CA $123

CA $134 total

Sep 30 - Oct 1

includes taxes & fees

Stay at this hotel in Tilton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Silver Lake and Lochmere Golf & Country Club are located nearby.

Breakfast included

Parking included

The Naswa Resort

1086 Weirs Blvd Laconia NH

CA $220

CA $239 total

Oct 8 - Oct 9

includes taxes & fees

Book a stay at this beach resort in Laconia. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Bank of New Hampshire Pavilion at Meadowbrook and Winnipesaukee Playhouse are located nearby.

On private beach

Parking included

Don't see what you're looking for?

See all available properties in Pittsfield

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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.

See properties

Pittsfield Vacations

If you're vacationing in Pittsfield and you don't really know a great deal about it, don't worry — we can fill you in!

This town is located 9 miles (14 kilometers) northeast of Pembroke. You'll also find it 13 miles (21 kilometers) northeast of Concord.

2,000 friendly locals reside in this part of New Hampshire.

Places to visit in Pittsfield

Ever wondered what Saturn's rings are made of or just what a black hole is? Learn all about the stars, moons and the mysteries of the universe at Christa McAuliffe Planetarium. Want more ideas? Ever wondered how people lived without the mod cons we enjoy today? Amble down the old streets of Canterbury Shaker Village and experience life as it was lived many years ago.

Where do you fly into for Pittsfield?

While you're researching for your Pittsfield escape, bear in mind that the closest terminal, Manchester-Boston Regional Airport (MHT), is approximately 25 miles (40 kilometers) south of the main streets. Book your flights, fill up your suitcase and get ready for an once-in-a-lifetime adventure!

Frequently asked questions

How much are vacation packages to Pittsfield?

With Travelocity vacation packages, you could live it up in Pittsfield from just CA $1,350. 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 105 kilometers 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 88 kilometers northeast of the bustling downtown area. Your other choices are Manchester-Boston Regional Airport (MHT) (40 kilometers away from central Pittsfield) and Lebanon Municipal Airport (LEB) (88 kilometers 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.