Deals on vacations and trips to Pittsfield

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Pittsfield flight + hotel vacation packages

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Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Save 100% on your flight
Price was $739, price is now $392 per person
$392
per person
Nov 8 - Nov 10
found 1 day ago
Roundtrip non-stop 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.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was $3,207, price is now $1,479 per person
$1,479
per person
Dec 11 - Dec 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Embassy Suites Boston Logan Airport

Embassy Suites Boston Logan Airport

3.5 out of 5
East Boston
Save 100% on your flight
Price was $980, price is now $633 per person
$633
per person
Dec 11 - Dec 18
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 24-hour business center, express check-in, and free airport shuttle. Enjoy the gym and perks like free train station pick-up.
XV Beacon

XV Beacon

5 out of 5
Beacon Hill
Save 100% on your flight
Price was $1,912, price is now $1,318 per person
$1,318
per person
Dec 10 - Dec 15
found 2 hours ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and airport shuttle. Valet parking, limo/town car service, and dry cleaning are also offered.
Hampton Inn Boston Logan Airport Chelsea

Hampton Inn Boston Logan Airport Chelsea

2.5 out of 5
Save 100% on your flight
Price was $902, price is now $628 per person
$628
per person
Dec 11 - Dec 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
A gym, self parking, and laundry facilities are featured at this hotel. Guests will appreciate freebies like continental breakfast, WiFi in public areas, and a roundtrip airport shuttle. Luggage storage and a safe deposit box are also provided.

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
$79 nightly
The price is $86 total per night
$86 total
Oct 13 - Oct 14
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
The Centennial

The Centennial

4 out of 5
96 Pleasant St, Concord, NH
Free Cancellation
Reserve now, pay when you stay
$145 nightly
The price is $157 total per night
$157 total
Nov 2 - Nov 3
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 4 conference rooms, free WiFi in public areas, and express check-out. Guests will appreciate freebies like continental breakfast and free self parking.
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
$84 nightly
The price is $91 total per night
$91 total
Nov 2 - Nov 3
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.
The Naswa Resort

The Naswa Resort

3 out of 5
1086 Weirs Blvd, Laconia, NH
$159 nightly
The price is $173 total per night
$173 total
Oct 5 - Oct 6
Total with taxes and fees
This smoke-free resort features a private beach and 2 restaurants. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas.
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
$101 nightly
The price is $110 total per night
$110 total
Nov 2 - Nov 3
Total with taxes and fees
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.
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
$126 nightly
The price is $137 total per night
$137 total
Oct 26 - Oct 27
Total with taxes and fees
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.
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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 $392. 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