Deals on vacations and trips to Pittsfield

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Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $838, price is now $314 per person
$314
per person
Jan 23 - Jan 26
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was $1,829, price is now $909 per person
$909
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
Fenway–Kenmore
Save 100% on your flight
Price was $604, price is now $349 per person
$349
per person
Jan 24 - Jan 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. A coffee shop, a communal living room, and express check-in are also on offer.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,238, price is now $745 per person
$745
per person
Jan 29 - Feb 1
found 15 hours 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. Enjoy the indoor pool and perks like free WiFi.
The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Save 100% on your flight
Price was $896, price is now $549 per person
$549
per person
Mar 6 - Mar 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
A full-service spa, 3 restaurants, and a 24-hour gym are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Self parking, limo/town car service, and a snack bar/deli are also offered.

Top Pittsfield hotels deals

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 $107 total per night
$107 total
Dec 28 - Dec 29
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
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
$149 nightly
The price is $162 total per night
$162 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This cabin includes express check-out and a virtual front desk. Take advantage of the free self parking.
Kitchen
Pet friendly
Winnisquam Lake Inn

Winnisquam Lake Inn

3 out of 5
788 Laconia Rd Tilton NH
Get rates
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
$154 nightly
The price is $168 total per night
$168 total
Dec 22 - Dec 23
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.
Breakfast included
Pet friendly
Microtel Inn & Suites by Wyndham Dover

Microtel Inn & Suites by Wyndham Dover

2 out of 5
31 Webb Pl Dover NH
Free Cancellation
Reserve now, pay when you stay
$84 nightly
The price is $91 total per night
$91 total
Dec 22 - Dec 23
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. A lobby fireplace, a picnic area, and a computer station are also on offer.
Breakfast included
Pet friendly
TownePlace Suites by Marriott Gilford

TownePlace Suites by Marriott Gilford

3 out of 5
14 Sawmill Road Gilford NH
Free Cancellation
Reserve now, pay when you stay
$139 nightly
The price is $151 total per night
$151 total
Jan 20 - Jan 21, 2026
Total with taxes and fees
A full-service spa and an indoor pool are featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and free perks like continental 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

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 $314. 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