Pittsfield Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to €185 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top Flight + Hotel Deals in Pittsfield

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

YOTEL Boston

4 out of 5
Seaport District
per person
25 Aug - 28 Aug
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
8.6/10 Excellent! (2,098 reviews)
Safe location. Clubs across the street for a night out. Fairly close to tourist things. Rooms are clean but on the smaller side.

Reviewed on 24 Jul 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
25 Aug - 28 Aug
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
I made a mistake on my room type when I made the reservation, they hotel was extremely helpful in helping me get it corrected. The hotel is beautiful, the location/views are amazing, and the food at the hotel restaurant was outstanding.

Reviewed on 23 Jul 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
per person
25 Aug - 28 Aug
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (1,003 reviews)
We enjoyed our stay very much, the staff is super friendly, rooms are very clean, the restaurants offer delicious meals, breakfast are simply amazing ❤️

Reviewed on 23 Jul 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
per person
25 Aug - 28 Aug
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (122 reviews)
Excellent, elegant, great service in every way possible. Friendly, helpful and responsive staff too.

Reviewed on 14 Jul 2025

Hampton Inn Boston Seaport District

Hampton Inn Boston Seaport District

3 out of 5
Seaport District
per person
25 Aug - 28 Aug
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.2/10 Wonderful! (2,411 reviews)
Great location in the Seaport area of Boston. The property is clean and the staff was excellent. The only issue I had was that breakfast was served only until 9 am. While this isn’t a big deal it did cause quite the chaos with guests all coming around the same time causing long lines and difficulty finding a place to sit. Having breakfast open until at least 10 am or even 11 am would mitigate this.

Reviewed on 25 Jul 2025

Top hotels in Pittsfield

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 €74 per night from 4 Aug to 5 Aug
€74
4 Aug - 5 Aug
includes taxes & fees
6.8/10 (647 reviews)
"nothing"

Reviewed on 21 Jul 2025

Winnisquam Lake Inn
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 €101 per night from 31 Jul to 1 Aug
€101
31 Jul - 1 Aug
includes taxes & fees
7.6/10 Good! (1,015 reviews)
"Staff was nice and very helpful. Room was clean and comfortable."

Reviewed on 21 Jul 2025

Best Western Plus Landmark Inn
Microtel Inn & Suites by Wyndham Dover

Microtel Inn & Suites by Wyndham Dover

2 out of 5
31 Webb Pl, Dover, NH
Fully refundableReserve now, pay when you stay
The price is €110 per night from 4 Aug to 5 Aug
€110
4 Aug - 5 Aug
includes taxes & fees
7.8/10 Good! (1,005 reviews)
"We had never stayed at a Microtel and were pleasantly surprised. The room was larger than expected, very clean and comfortable. The only suggestion I would make is to move the outdoor ashtray away from the front door, initial entry to lobby smells like an old bowling alley."

Reviewed on 22 Jul 2025

Microtel Inn & Suites by Wyndham Dover
See all 1,168 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.

Frequently asked questions

How much does a Pittsfield holiday package cost?
You'll find cheap prices from €884 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.

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