Deals on vacations and trips to Pittsfield

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Pittsfield flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
Price was $1,031, price is now $692 per person
$692
per person
Jun 22 - Jun 24
found 3 hours ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
A restaurant and a bar/lounge are featured at this hotel. A terrace, limo/town car service, and a snack bar/deli are also on offer.
Summer House Hotel

Summer House Hotel

2 out of 5
Save 100% on your flight
Price was $2,233, price is now $1,484 per person
$1,484
per person
May 23 - May 30
found 15 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
This hotel features a private beach and 2 restaurants. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like continental breakfast and WiFi in public areas. Enjoy the seasonal outdoor pool and unwind at the beach bar and poolside bar.
The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was $3,033, price is now $2,064 per person
$2,064
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the 24-hour gym and perks like free WiFi.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,772, price is now $1,211 per person
$1,211
per person
May 16 - May 18
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) 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.
The Westin Waltham-Boston

The Westin Waltham-Boston

4 out of 5
Price was $1,232, price is now $882 per person
$882
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

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
This cabin includes a garden and barbecue grills.
Kitchen
Outdoor Space
Steele Hill Resorts

Steele Hill Resorts

3 out of 5
516 Steele Hill Road Sanbornton NH
$189 nightly
The price is $205 total per night
$205 total
Apr 8 - Apr 9
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
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
$105 nightly
The price is $114 total per night
$114 total
Apr 15 - Apr 16
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
Winnisquam Lake Inn

Winnisquam Lake Inn

3 out of 5
788 Laconia Rd Tilton NH
Free Cancellation
Reserve now, pay when you stay
$79 nightly
The price is $86 total per night
$86 total
May 7 - May 8
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
Best Western Concord Inn & Suites

Best Western Concord Inn & Suites

2.5 out of 5
97 Hall St Concord NH
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $124 total per night
$124 total
Apr 19 - Apr 20
Total with taxes and fees
This hotel features an indoor pool and a gym. Enjoy the hot tub and free perks like on-the-go breakfast and free self parking. A business center, free WiFi in public areas, and express check-out are also on offer.
Pool
Hot Tub
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
$98 nightly
The price is $106 total per night
$106 total
May 7 - May 8
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
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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

Drake Field

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

Drake Field

Pittsfield Town Hall

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

Pittsfield Town Hall

Frequently asked questions

How much are vacation packages to Pittsfield?
With Travelocity vacation packages, you could live it up in Pittsfield from just $692. 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.

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.