Book Exclusive Pittsfield Vacation Packages

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Pittsfield flight + hotel packages

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

Iris Hotel Boston

4 out of 5
Coolidge Corner South Side
Price was CA $1,306, price is now CA $930 per person
CA $930
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
Stay at this 4-star business-friendly hotel in Brookline. Enjoy free WiFi, breakfast (surcharge), and room service. Popular attractions Fenway Park and Harvard Square are located nearby.
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was CA $2,015, price is now CA $1,052 per person
CA $1,052
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
Stay at this 4-star luxury hotel in Lexington. Enjoy room service, free bicycles on site, and onsite spa services. Our guests praise the helpful staff in our reviews. Popular attractions Lexington Battle Green and Burlington Mall are located nearby.
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $2,166, price is now CA $1,263 per person
CA $1,263
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
Stay at this 5-star 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.
The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Price was CA $1,594, price is now CA $1,042 per person
CA $1,042
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
Stay at this 4-star luxury hotel in Cambridge. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Harvard Square and Fenway Park are located nearby.
The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $1,542, price is now CA $1,095 per person
CA $1,095
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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 Faneuil Hall Marketplace and New England Aquarium are located nearby.

Top Pittsfield hotels deals

Winnisquam Lake Inn

Winnisquam Lake Inn

3 out of 5
788 Laconia Rd, Tilton, NH
Free cancellation
Reserve now, pay when you stay
The price is CA $118 per night
CA $118
CA $128 total
Oct 26 - Oct 27
includes taxes & fees
Stay at this 3-star 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 Lochmere Golf & Country Club and Sanbornton Public Library are located nearby.
Breakfast included
Parking included
Best Western Plus Landmark Inn

Best Western Plus Landmark Inn

2.5 out of 5
480 Main Street, Laconia, NH
Free cancellation
Reserve now, pay when you stay
The price is CA $141 per night
CA $141
CA $154 total
Nov 2 - Nov 3
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 Bank of New Hampshire Pavilion at Meadowbrook and Gunstock Mountain Resort are located nearby.
Pool
Breakfast included
Hampton Inn by Hilton Concord/Bow

Hampton Inn by Hilton Concord/Bow

2.5 out of 5
515 South St, Bow, NH
Free cancellation
Reserve now, pay when you stay
The price is CA $114 per night
CA $114
CA $123 total
Nov 2 - Nov 3
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
Fairfield Inn By Marriott Concord

Fairfield Inn By Marriott Concord

2.5 out of 5
4 Gulf St, Concord, NH
Free cancellation
Reserve now, pay when you stay
The price is CA $173 per night
CA $173
CA $188 total
Nov 2 - Nov 3
includes taxes & fees
Book a stay at this business-friendly hotel in Concord. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Capitol Center for the Arts and Rotary Park are located nearby.
Pool
Breakfast included
The Centennial

The Centennial

4 out of 5
96 Pleasant St, Concord, NH
Free cancellation
Reserve now, pay when you stay
Get rates
Stay at this 4-star business-friendly hotel in Concord. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Capitol Center for the Arts and New Hampshire Historical Society are located nearby.
Breakfast included
Pet-friendly
The Naswa Resort

The Naswa Resort

3 out of 5
1086 Weirs Blvd, Laconia, NH
Get rates
Stay at this 3-star 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 Gunstock Mountain Resort are located nearby.
On private beach
Parking included
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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.

Popular places to visit

Harold Conrad Square

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

Harold Conrad Square

Josiah Carpenter Library

Josiah Carpenter Library is just one of the places to see in Pittsfield, so why not enjoy the other things to explore during your travels?

Josiah Carpenter Library

Scenic Theatre

You can enjoy a show at Scenic Theatre on your trip to Pittsfield.

Scenic Theatre

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 $930. 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.

Photos of local treasures

Browse Pittsfield vacation photos for more inspiration