Pittsfield Vacations from $925

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The Latest Pittsfield vacation packages

Price found within the past 48 hours. Click for updated prices.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was $1,691, price is now $925 per person
$925
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)
We were there for 5 days. It was impeccable. The location, service, ambiance everything was perfect! All small attentions that makes you feel comfortable. We took the water taxi from (and to) the airport directly to the hotel fastest way to get there. Easy to walk around and along the waterfront. Breakfast was excellent

Reviewed on Jun 15, 2026

Meco Hotel - Hostel

Meco Hotel - Hostel

2 out of 5
West End
Save 100% on your flight
Price was $1,712, price is now $1,073 per person
$1,073
per person
Aug 30 - Sep 5
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.6/10 Excellent! (457 reviews)
Spacious, nice LOCKABLE drawers under beds!

Reviewed on Jun 16, 2026

Chatham Tides

Chatham Tides

2.5 out of 5
Save 100% on your flight
Price was $3,358, price is now $2,112 per person
$2,112
per person
Aug 8 - Aug 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (707 reviews)
It was absolutely charming and beautiful! The view was magnificent, the staff couldn't have been more accommodating and the room was wonderful. I would return to Room 23 over and over again.

Reviewed on Jun 20, 2026

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $2,701, price is now $1,706 per person
$1,706
per person
Aug 30 - Sep 5
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (657 reviews)
Incredible staff. This is an amazing location and the breakfast is great

Reviewed on Jun 16, 2026

Furnished Apartment Near Longwood

Furnished Apartment Near Longwood

3 out of 5
North Brookline
Save 100% on your flight
Price was $1,872, price is now $1,204 per person
$1,204
per person
Aug 30 - Sep 5
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
7.4/10 Good! (3 reviews)
Easy to check in, students friendly apartment, convenient location, easy to call Uber or Lyft, and within 20 min. drive to the famous universities.

Reviewed on Apr 1, 2026

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Pittsfield Hotel 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
10/10 Exceptional! (38 reviews)
"The cabin had everything we needed for a perfect peaceful getaway"

Reviewed on May 3, 2026

Get rates
Bower Cabin- Cabin in woods on a remote pond, Romantic getaway, Green living!
Best Western Plus Landmark Inn

Best Western Plus Landmark Inn

2.5 out of 5
480 Main Street Laconia NH
Fully refundableReserve now, pay when you stay
$112 nightly
The price is $122 total per night from Jun 22 to Jun 23
$122 total
Jun 22 - Jun 23
Total with taxes and fees
7.8/10 Good! (1,005 reviews)
"Very unclean and old. Our sheets had many runs in them. Floors dirty, room smelled. Just not a pleasant stay at all."

Reviewed on Jun 20, 2026

Best Western Plus Landmark Inn
Comfort Inn Concord South End

Comfort Inn Concord South End

2.5 out of 5
71 Hall St Concord NH
Fully refundable
$105 nightly
The price is $114 total per night from Jul 12 to Jul 13
$114 total
Jul 12 - Jul 13
Total with taxes and fees
8.2/10 Very Good! (1,003 reviews)
"second time staying here during Laconia bike week. conveniently located hotel, clean, plenty of parking, and helpful staff. Ninas sandwich shop 2 min walk. great sandwiches family-owned business. 2 Home Fitness located next store. worked out there the whole week. nice gym. easy access to 89, 91 and ..."

Reviewed on Jun 20, 2026

Comfort Inn Concord South End
See all 1,252 properties in Pittsfield
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.

Find the Best Pittsfield Vacation Packages

Pittsfield Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Manchester-Boston Regional Airport (MHT)
Population
1,600

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Frequently asked questions

How much does a Pittsfield vacation package cost?
You'll find cheap prices from $925 on Expedia for your Pittsfield escape. However, a range of factors like the length of stay, hotel choice and season will determine how much your vacation to Pittsfield costs.
What are the cheapest months to go to Pittsfield?
You can generally find lower rates and better availability in November, December and January. Explore our cheap Pittsfield vacation packages and you could land some great off-season deals.
How many days is enough for Pittsfield?
Generally, a handful of days is enough to tick off the main sights during your Pittsfield vacation. However, if you'd like to have more time to relax or go on day tours, think about extending your itinerary.
How to find the best Pittsfield package deals?
Use Expedia's filters to find some tempting Pittsfield package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or browse for Pittsfield package deals in the off-peak season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Pittsfield vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging accommodations and flights individually. Better still, you can customize your Pittsfield escape to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Pittsfield?
Land amazing discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Pittsfield adventure.
Does Expedia offer Book Now, Pay Later Pittsfield vacation packages?
Set off on your perfect trip to Pittsfield with Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or wait for your next payday — we've teamed up with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans mean you can spread the total cost across 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily stick to your budget and snag great deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.