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.
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
Bay Village
Save 100% on your flight
per person
Jan 22 - Jan 27
found 22 hours ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
This historic hotel's 2 restaurants, 3 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A coffee shop, a garden, and a snack bar/deli are also on offer.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. There's a rooftop terrace on site, and laundry facilities and concierge services are also offered.
Sea Mist Resort by VRI Americas

Sea Mist Resort by VRI Americas

3 out of 5
per person
Mar 6 - Mar 11
found 1 hour ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
This aparthotel features an outdoor pool and an indoor pool. Business travelers can take advantage of the free WiFi in public areas. Enjoy the gym and perks like free self parking.
TownePlace Suites Boston Logan Airport/Chelsea

TownePlace Suites Boston Logan Airport/Chelsea

3 out of 5
Save 100% on your flight
per person
Jan 22 - Jan 27
found 22 hours ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy the free buffet breakfast each morning.
The Centennial

The Centennial

4 out of 5
Save 100% on your flight
per person
Feb 22 - Mar 1
found 3 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Manchester (MHT)
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.

Top Pittsfield hotels deals

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 $107 per night
$107
includes taxes & fees
$99 per night
Jan 19 - Jan 20, 2025
This hotel features an indoor pool and a spa 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
The Centennial

The Centennial

4 out of 5
96 Pleasant St, Concord, NH
Free Cancellation
Reserve now, pay when you stay
The price is $142 per night
$142
includes taxes & fees
$131 per night
Dec 30 - Dec 31
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
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
Jan 2 - Jan 3, 2025
This hotel's golf course, 2 indoor pools, and 2 outdoor tennis courts are some of the highlights. Bring the family and enjoy the children's pool, waterslide, and playground. Enjoy the 3 spa tubs and perks like free self parking and free WiFi.
Pool
Hot Tub
Fireside Inn & Suites Gilford

Fireside Inn & Suites Gilford

2.5 out of 5
17 Harris Shore Road, Gilford, NH
Free Cancellation
Reserve now, pay when you stay
The price is $167 per night
$167
includes taxes & fees
$154 per night
Dec 24 - Dec 25
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free internet in public areas. Enjoy the seasonal outdoor pool and free perks like on-the-go breakfast and free self parking.
Pool
Hot Tub
Holiday Inn Concord Downtown, an IHG Hotel

Holiday Inn Concord Downtown, an IHG Hotel

3 out of 5
172 N Main St, Concord, NH
Get rates
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
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
The price is $127 per night
$127
includes taxes & fees
$117 per night
Dec 24 - Dec 25
This hotel features an indoor pool and a gym. Enjoy the spa 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
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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.

Frequently asked questions

How much are vacation packages to Pittsfield?
With Travelocity vacation packages, you could live it up in Pittsfield from just $320. 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

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