Pittsfield Vacations from AED6,652

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The Latest Pittsfield Vacation Packages

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

YOTEL Boston

4 out of 5
Seaport District
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Abu Dhabi (AUH) to Boston (BOS)
8.6/10 Excellent! (1,978 reviews)
Staff was nice. Had breakfast downstairs in the lobby. Only had one person taking orders and serving customers for both the bar and dining room. I paid for valet parking. The valet did not keep up with the cars. Just left them out front. When I was trying to return there was no parking and no one to take my car. I tried to call the hotel and no one would answer the phone.

Reviewed on 31 March 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Abu Dhabi (AUH) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
The best stay I’ve ever had in Boston

Reviewed on 31 March 2025

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Chinatown
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Abu Dhabi (AUH) to Boston (BOS)
8/10 Very Good! (534 reviews)
Parking is just a hassle

Reviewed on 25 March 2025

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Abu Dhabi (AUH) to Boston (BOS)
8.8/10 Excellent! (1,006 reviews)
Staff was helpful and bed was very comfortable. However, aside from the mattress, the room needed an update. There was no mini fridge and no outlet next to the bed.

Reviewed on 30 March 2025

Hotel AKA Boston Common

Hotel AKA Boston Common

4 out of 5
Downtown Boston
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Abu Dhabi (AUH) to Boston (BOS)
8.8/10 Excellent! (1,072 reviews)
Great location, walkable to all that we wanted to see. Hotelroom was clean and quit. Staff was very friendly

Reviewed on 31 March 2025

Find the Best Pittsfield Vacation Packages

Pittsfield Hotel Deals

Steele Hill Resorts
Steele Hill Resorts
3 out of 5
516 Steele Hill Road, Sanbornton, NH
The price is AED 680 per night from Apr 1 to Apr 2
AED 680
AED 737 total
includes taxes & fees
1 Apr - 2 Apr
8.2/10 Very Good! (623 reviews)
"Liked everything"

Reviewed on 17 March 2025

Steele Hill Resorts
Fairfield Inn By Marriott Concord
Fairfield Inn By Marriott Concord
2.5 out of 5
4 Gulf St, Concord, NH
Fully refundableReserve now, pay when you stay
The price is AED 419 per night from Apr 11 to Apr 12
AED 419
AED 454 total
includes taxes & fees
11 Apr - 12 Apr
8.4/10 Very Good! (1,001 reviews)
Decent place
"Decent room, decent breakfast. Kind of a sketchy area. Rooms either face an extremely busy interstate or a garbage-filled area below train tracks."

Reviewed on 22 March 2025

Fairfield Inn By Marriott Concord
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 AED 356 per night from Apr 2 to Apr 3
AED 356
AED 387 total
includes taxes & fees
2 Apr - 3 Apr
7.6/10 Good! (1,001 reviews)
"Great location"

Reviewed on 16 March 2025

Best Western Plus Landmark Inn
See all 1,102 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 vacation package cost?
You’ll find cheap prices from AED6,652 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?
The off-season is the best time to travel to Pittsfield if you’re trying to save. Another tip for scoring cheap Pittsfield vacation packages? Avoid visiting during public holidays and any major events.
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.
How to plan a trip to Pittsfield?

  1. Choose when to go: Check your diary and pack your bags. Your favorite 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 accommodations 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 vacation package.