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.
Comfort Inn & Suites Sturbridge - Brimfield

Comfort Inn & Suites Sturbridge - Brimfield

2.5 out of 5
per person
May 18 - May 23
found 23 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like continental breakfast and free self parking.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Save 100% on your flight
per person
Jun 9 - Jun 12
found 2 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Free WiFi in public areas, a terrace, and a garden are available at this hotel. Families will appreciate the playground, onsite laundry facilities, and in-room childcare. A hair salon, a picnic area, and express check-out are also on offer.
Riverview Resort

Riverview Resort

3 out of 5
Bass River
Save 100% on your flight
per person
Jun 25 - Jun 29
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
This aparthotel features an indoor pool and a gym. Enjoy the hot tub and perks like free self parking and free WiFi. A 24-hour business center, a picnic area, and laundry facilities are also on offer.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
May 30 - Jun 2
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. Relax with a drink at the bar/lounge and enjoy perks like free WiFi.
Ginkgo House on Harvard

Ginkgo House on Harvard

3 out of 5
Mid-Cambridge
Save 100% on your flight
per person
Jun 10 - Jun 14
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Free WiFi in public areas, a garden, and a picnic area are available at this inn. Express check-in, express check-out, and dry cleaning are also on offer.

Top Pittsfield hotels deals

Steele Hill Resorts

Steele Hill Resorts

3 out of 5
516 Steele Hill Road, Sanbornton, NH
The price is $201 per night
$201
includes taxes & fees
$185 per night
Apr 6 - Apr 7
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
Holiday Inn Express Hotel & Suites Tilton - Lakes Region by IHG

Holiday Inn Express Hotel & Suites Tilton - Lakes Region by IHG

2.5 out of 5
75 Tilton Road, NH Route 140, Tilton, NH
Free Cancellation
The price is $128 per night
$128
includes taxes & fees
$118 per night
Apr 9 - Apr 10
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast 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 $110 per night
$110
includes taxes & fees
$101 per night
Apr 6 - Apr 7
This hotel features an indoor pool and a 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
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 $124 per night
$124
includes taxes & fees
$114 per night
Apr 11 - Apr 12
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Breakfast included
Comfort Inn Concord

Comfort Inn Concord

2.5 out of 5
71 Hall St, Concord, NH
Free Cancellation
Reserve now, pay when you stay
The price is $116 per night
$116
includes taxes & fees
$107 per night
Apr 20 - Apr 21
This hotel features an indoor pool and a hot tub. Business travelers can take advantage of the free WiFi in public areas. Enjoy the sauna and free perks like continental breakfast and free self parking.
Pool
Hot Tub
Tru by Hilton Concord

Tru by Hilton Concord

2.5 out of 5
South Main Street, 406, Concord, NH
Free Cancellation
Reserve now, pay when you stay
The price is $126 per night
$126
includes taxes & fees
$116 per night
Apr 18 - Apr 19
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls and litter boxes. A 24-hour gym and a safe deposit box are also provided.
Breakfast included
Pet friendly
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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

Frequently asked questions

How much are vacation packages to Pittsfield?
With Travelocity vacation packages, you could live it up in Pittsfield from just $455. 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