Pittsfield Holidays

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Top Flight + Hotel Deals in Pittsfield

Price found within the past 48 hours. Click for updated prices.
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4 out of 5
Seaport District
per person
18 Sept - 22 Sept
found 18 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.2/10 Wonderful! (3,781 reviews)
Pool was great. Close to seaport.

Reviewed on 7 Aug 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
19 Sept - 22 Sept
found 18 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.8/10 Exceptional! (1,014 reviews)
Wonderful high end hotel in a fantastic area. Loved being able to walk to the north end!

Reviewed on 3 Aug 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
19 Sept - 22 Sept
found 18 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (135 reviews)
I had high expectations since we have been to Raffles Singapore before and after the recent renovations and it is one of our favorite hotels in the world! Glad to say that Raffles Boston did not disappoint. The hotel decor is gorgeous, thoughtfully luxurious in every detail. Location is great. Service is professional but friendly. The room butler is a convenience that cannot be overstated. Also, the first hotel that actually kept the room temperature at 66 F during the whole night. Adios, Four Seasons! Raffles is my new home in Boston.

Reviewed on 5 Aug 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
per person
19 Sept - 22 Sept
found 18 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (1,005 reviews)
Very convenient boutique hotel

Reviewed on 5 Aug 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
per person
19 Sept - 22 Sept
found 18 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (428 reviews)
Had an amazing time at the Whitney. Front desk service was impeccable, friendly and was ‘just’ the added touch I would expect of a property of this caliber. I really do look forward to my next time in Boston and hope to stay at the Whitney.

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 7 Sept to 8 Sept
€74
7 Sept - 8 Sept
includes taxes & fees
6.8/10 (674 reviews)
"The beach area was a danger to get to. Had to cross a very busy highway and walk down a steep hill. Breakfast was skimpy and late."

Reviewed on 5 Aug 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 €114 per night from 10 Aug to 11 Aug
€114
10 Aug - 11 Aug
includes taxes & fees
7.6/10 Good! (1,016 reviews)
Worth the trip
"Friendly , professional and worth the trip!"

Reviewed on 4 Aug 2025

Best Western Plus Landmark Inn
Weirs Beach Motel and Cottages

Weirs Beach Motel and Cottages

2 out of 5
396 Lakeside Ave, Laconia, NH
8/10 Very Good! (659 reviews)
"Nice an cozy ..walk distance to board walk"

Reviewed on 3 Aug 2025

Get rates
Weirs Beach Motel and Cottages
See all 1,166 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 €819 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.