Pittsfield Holidays

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Top Flight + Hotel Deals in Pittsfield

Price found within the past 48 hours. Click for updated prices.
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
South End
Price was €1,483, price is now €1,104 per person
€1,104
per person
1 Sept - 8 Sept
found 21 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (2,710 reviews)

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was €3,656, price is now €1,876 per person
€1,876
per person
1 Sept - 8 Sept
found 21 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Great location and very helpful staff

Reviewed on 16 Jul 2026

The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
Downtown Boston
Save 100% on your flight
Price was €2,009, price is now €1,293 per person
€1,293
per person
1 Sept - 8 Sept
found 21 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (5,113 reviews)
So impressed with this hotel. Snacks and water were free in the rooms. The staff was super helpful - clean rooms. Bar within the the hotel as well as a cafe.

Reviewed on 16 Jul 2026

Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Downtown Boston
Save 100% on your flight
Price was €1,909, price is now €1,386 per person
€1,386
per person
1 Sept - 8 Sept
found 21 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (3,186 reviews)
The hotel is in a great location with dining, shopping, and attractions in walking distance. The staff was very helpful and professional. The room was clean and the bed very comfortable. But, the property overall is a bit worn and could use a recess.

Reviewed on 16 Jul 2026

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was €1,816, price is now €1,330 per person
€1,330
per person
1 Sept - 8 Sept
found 21 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
8.8/10 Excellent! (1,524 reviews)
Not really sure what the amenities were but in a great location

Reviewed on 16 Jul 2026

Top hotels in Pittsfield

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
The price is €117 per night from 5 Aug to 6 Aug
€117
5 Aug - 6 Aug
includes taxes & fees
7.8/10 Good! (1,007 reviews)
"Could use some renovation"

Reviewed on 16 Jul 2026

Best Western Plus Landmark Inn
The Naswa Resort

The Naswa Resort

3 out of 5
1086 Weirs Blvd Laconia NH
The price is €246 per night from 19 Jul to 20 Jul
€246
19 Jul - 20 Jul
includes taxes & fees
The Naswa Resort
Winnisquam Lake Inn

Winnisquam Lake Inn

3 out of 5
788 Laconia Rd Tilton NH
Fully refundableReserve now, pay when you stay
The price is €84 per night from 28 Jul to 29 Jul
€84
28 Jul - 29 Jul
includes taxes & fees
6.8/10 (899 reviews)
"Great central location. This property suffers from a lack of maintenance as decking, landscaping and building basic repairs are severely lacking. The linen is inexpensive stained and discolored. Tiny room, struggled with the key system, no desk staff after nine."

Reviewed on 16 Jul 2026

Winnisquam Lake Inn
See all 1,243 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.

Stay near popular Pittsfield attractions

Harold Conrad Square

This quaint community park in Pittsfield offers a peaceful retreat for quiet reflection and leisurely walks. Bring a picnic lunch and explore the historic churches nearby for a charming small-town experience.
See properties

Frequently asked questions

How much does a Pittsfield holiday package cost?
You'll find cheap prices from €1,104 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 holiday to Pittsfield costs.
What are the cheapest months to go to Pittsfield?
The off-season is the best time to travel to Pittsfield if you're trying to save. Another tip for scoring cheap Pittsfield holiday packages? Avoid visiting during public holidays and any major events.
How many days is enough for Pittsfield?
The ideal length of your Pittsfield holiday depends on what you'd like to do. Typically, a handful of days to a week will give you enough time to check out all the major attractions and discover some hidden spots along the way.
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 holiday package as soon as possible.
Is it cheaper to book a Pittsfield holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging accommodation and flights individually. Better still, you can customise 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 holiday 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.
How to plan a trip to Pittsfield?

  1. Choose when to go: Check your diary and pack your bags. Your favourite season and the type of activities available will also help you decide when to visit Pittsfield.
  2. Calculate your budget: Make sure you have enough money to pay for everything from food and transportation to activities and flights. Your accommodation will likely be the biggest expense during your trip to Pittsfield.
  3. Set the duration of your trip: Start by making a list of all the attractions and activities you'd like to get to in Pittsfield. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a tailored Pittsfield holiday package.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.