Book Exclusive Pittsfield Vacation Packages

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Pittsfield flight + hotel packages

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

Lighthouse Inn

3 out of 5
Price was CA $2,038, price is now CA $1,431 per person
CA $1,431
per person
Jul 10 - Jul 14
found 13 hours ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
Book a stay at this beach hotel in West Dennis. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Hyannis Harbor and Main Street Hyannis are located nearby.
The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $4,806, price is now CA $3,283 per person
CA $3,283
per person
Jun 15 - Jun 19
found 24 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 clean rooms in our reviews. Popular attractions New England Aquarium and Boston Harbor are located nearby.
The Atlas Hotel

The Atlas Hotel

4.5 out of 5
Allston
Price was CA $2,153, price is now CA $1,517 per person
CA $1,517
per person
Jun 21 - Jun 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Popular attractions Harvard Square and Fenway Park 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 $2,081, price is now CA $1,467 per person
CA $1,467
per person
Jun 21 - Jun 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
Book a stay at this 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.
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was CA $2,097, price is now CA $1,488 per person
CA $1,488
per person
Jun 15 - Jun 19
found 24 hours ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
Book a stay at this boutique hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions TD Garden and Boston Common are located nearby.

Top Pittsfield hotels deals

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

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

Pittsfield NH
Get rates
Stay at this cabin in Pittsfield. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Kooaukee Island and Little Kooaukee Island are located nearby.
Kitchen
Outdoor space
Steele Hill Resorts

Steele Hill Resorts

3 out of 5
516 Steele Hill Road Sanbornton NH
The price is CA $258 per night
CA $258
CA $280 total
Apr 27 - Apr 28
includes taxes & fees
Book a stay at this spa hotel in Sanbornton. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Ahern State Park and Sanbornton Public Library are located nearby.
Pool
Hot tub
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 $122 per night
CA $122
CA $132 total
May 3 - May 4
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 Lochmere Golf & Country Club and Sanbornton Public Library are located nearby.
Breakfast included
Parking included
Fairfield Inn By Marriott Concord

Fairfield Inn By Marriott Concord

3 out of 5
4 Gulf St Concord NH
Free cancellation
Reserve now, pay when you stay
The price is CA $169 per night
CA $169
CA $184 total
Apr 28 - Apr 29
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
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

2 out of 5
76 Mountain Rd Epsom NH
The price is CA $161 per night
CA $161
CA $234 total
May 27 - May 28
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
Comfort Inn Concord South End

Comfort Inn Concord South End

2.5 out of 5
71 Hall St Concord NH
Free cancellation
The price is CA $150 per night
CA $150
CA $163 total
May 10 - May 11
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 breakfast and the helpful staff in our reviews. Popular attractions Capitol Center for the Arts and Rotary Park are located nearby.
Pool
Breakfast 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

Pittsfield Town Hall

After visiting Pittsfield Town Hall, make a plan to see the other sights and activities in Pittsfield.

Pittsfield Town Hall

Harold Conrad Square

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

Harold Conrad Square

Drake Field

After visiting Drake Field, make a plan to see the other sights and activities in Pittsfield.

Drake Field

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 $1,431. 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

Lake Autumn Foliage fog
Panoramic view of rural Vermont in autumn time.
Reflection of Mount Monadnock on Perkins Pond in Autumn
Sugar Hill Scenic Vista in Autumn on the Kancamagus Scenic Highway - White Mountain New Hampshire
Aerial view of vibrant fall foliage painting the landscape around scattered houses and a tranquil pond, with rolling hills beyond, in the White Mountains. Sugar Hill, New Hampshire, United States.