Pittsfield Holidays

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Top hotels in Pittsfield

Peek'n Peak Resort Trademark Collection by Wyndham

Peek'n Peak Resort Trademark Collection by Wyndham

3.5 out of 5
1405 Olde Road, Clymer, NY
Fully refundableReserve now, pay when you stay
The price is HK$598 per night from 3 Aug to 4 Aug
HK$598
HK$912 total
3 Aug - 4 Aug
includes taxes & fees
8.4/10 Very Good! (932 reviews)
Great weekend
"I took my girlfriend there for her birthday. We had a great time.Should I bI took my girlfriend there for her birthday. We had a great time. Sat by the pool relaxed. Then went to a margaritaville theme party outside, very, very nice, cool Good music. This staff is very nice, very courteous. Helpful ..."

Reviewed on 19 Jul 2025

Peek'n Peak Resort Trademark Collection by Wyndham
La Quinta Inn & Suites by Wyndham Jamestown

La Quinta Inn & Suites by Wyndham Jamestown

3 out of 5
200 W 3rd St, Jamestown, NY
The price is HK$901 per night from 4 Aug to 5 Aug
HK$901
HK$1,018 total
4 Aug - 5 Aug
includes taxes & fees
8.4/10 Very Good! (1,013 reviews)
"The building was in overall good shape, not excellent (peeling paint in the bathrooms, etc), but overall good. Breakfast was very good each of the 4 mornings I was there. The biggest drawback is the severe lack of parking at this facility. Since I went out to eat most evenings, all spaces were taken ..."

Reviewed on 22 Jul 2025

La Quinta Inn & Suites by Wyndham Jamestown
Clarion Pointe Jamestown - Falconer

Clarion Pointe Jamestown - Falconer

2.5 out of 5
2800 North Main Street EXT, Jamestown, NY
Fully refundableReserve now, pay when you stay
The price is HK$876 per night from 24 Jul to 25 Jul
HK$876
HK$990 total
24 Jul - 25 Jul
includes taxes & fees
8/10 Very Good! (901 reviews)
Friendly staff and receive pets
"All the staff were kind and friendly. Good quality but basic breakfast. Everything worked well but some renovations could be done in bathrooms."

Reviewed on 8 Jul 2025

Clarion Pointe Jamestown - Falconer
See all 427 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 on Expedia for your Pittsfield getaway. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your holiday to Pittsfield costs.
What are the cheapest months to go to Pittsfield?
If you'd like to score a cheap Pittsfield holiday package, consider planning a trip in January, February and March. You're likely to find lower prices on accommodation and flights during these quieter months — perfect for a budget-friendly getaway.
How many days is enough for Pittsfield?
Usually, a handful of days is enough to see the main attractions during your Pittsfield holiday. But if you prefer to have some time to rest or take day tours, think about extending your trip.
How to find the best Pittsfield package deals?
Start your search for a Pittsfield package deal by entering your destination and travel dates under our "Packages" tab. Then apply some filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Pittsfield package deal right away, just switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Pittsfield getaway off to a flying start.
Is it cheaper to book a Pittsfield holiday as a package?
You can enjoy significant savings on your next Pittsfield escape by booking a customised holiday package. Click on the "Package" heading, then enter your travel dates and destination to browse some great hotel prices and airfares. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a holiday package to Pittsfield?
Secure amazing discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for a spur-of-the-moment Pittsfield adventure.
How to plan a trip to Pittsfield?

  1. Pick the ideal time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to visit Pittsfield.
  2. Budget wisely: In addition to the price of your stay, you'll need to consider other expenses too. These include flights, transportation and food. Also, put aside some extra funds for unexpected costs that could crop up during your trip to Pittsfield.
  3. Decide how long to go away for: Now that you're up to speed on Pittsfield, you can work out the ideal length of your holiday. Create a rough plan and give yourself enough time to cover everything you want to do.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to pick a Pittsfield holiday package that brings all your bookings together.

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