Peekskill Vacations from $218

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Your Peekskill Vacation

Organizing your next big adventure is easy with a Peekskill vacation package. The neighborhood of Montrose, which is great for walking, makes a superb base to uncover the wonders of this city. If your trip to Peekskill includes some sightseeing, visit major attractions such as Franklin D. Roosevelt State Park, Paramount Hudson Valley Theater and Charles Point Pier Park. No matter your travel plans or budget, organizing a tailored Peekskill vacation is a piece of cake with Expedia.

The Latest Peekskill vacation packages

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

2 out of 5
per person
Aug 20 - Aug 23
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
5.4/10 (1,009 reviews)
When i checked in they gave me a room key walked up the second floor opened door and the room was trashed and looks like people already had the room walked back down to front desk the person behind the desk apologized and gave me a new room other then that the stay was nice the new room was clean

Reviewed on Jun 23, 2025

Hotel NoMa, Trademark Collection by Wyndham

Hotel NoMa, Trademark Collection by Wyndham

3 out of 5
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
8/10 Very Good! (1,004 reviews)
It was a nice experience, just didn’t like that i had to call for a microwave

Reviewed on Jun 29, 2025

Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
per person
Sep 18 - Sep 21
found 13 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to White Plains (HPN)
7.8/10 Good! (1,041 reviews)
We were given the smallest room on the floor and wonder if it was that we booked through Expedia. Carpet had big stains. Beds were comfortable and clean. No towel hooks and room service every other day.

Reviewed on Jun 30, 2025

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
per person
Aug 2 - Aug 5
found 4 hours ago
Roundtrip flight included
San Juan (SJU) to Newburgh (SWF)
8.6/10 Excellent! (1,003 reviews)
It was just right for our family.

Reviewed on Jun 28, 2025

Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
per person
Aug 14 - Aug 16
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
8.2/10 Very Good! (650 reviews)
Loved facility...nice customer service.

Reviewed on Jun 24, 2025

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Discover the most popular places to visit in Peekskill

Spent a foggy morning looking for bald eagles. Did not see any but enjoyed the walk.

Charles Point Pier Park

Charles Point Pier Park is just one of the places to see in Peekskill, so why not enjoy the other things to explore during your travels? While you're in the area, stroll along the riverfront.

Charles Point Pier Park
Great park and a lovely waterfront walk. Wonderful place to catch a sunset.

Peekskill Landing Park

Peekskill Landing Park is just one of the places to see in Peekskill, so why not enjoy the other things to explore during your travels? While you're in the area, stroll along the riverfront.

Peekskill Landing Park

Paramount Hudson Valley Theater

You can enjoy a show at Paramount Hudson Valley Theater on your trip to Peekskill. While you're in the area, stroll along the riverfront.

Paramount Hudson Valley Theater

What to do in Peekskill

Guided Shared Group Forest Bathing Session in Serene Woodland Park

Guided Shared Group Forest Bathing Session in Serene Woodland Park

$40
per adult
Guided Shared Group Forest Bathing Session in Serene Woodland Park
Cafe and Bakery Tour Explore Peekskill by Foot

Peekskill New York Culture and Food Walking Tour

$150
per adult
Peekskill New York Culture and Food Walking Tour
New York Thift, Outlet, and Consignment Shopping Tour

NY Thrift Shopping & Wine Tour

$399
per adult
NY Thrift Shopping & Wine Tour
See all activities in Peekskill

Peekskill Hotel Deals

Inn on the Hudson
Inn on the Hudson
2 out of 5
634 Main Street, Peekskill, NY
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $148 total per night from Jul 1 to Jul 2
$148 total
Jul 1 - Jul 2
Total includes taxes and fees
6.8/10 (1,001 reviews)
"Close proximity to the train & beautiful views of the Hudson!"

Reviewed on Jun 28, 2025

Inn on the Hudson
Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG
Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG
2.5 out of 5
2 John Walsh Boulevard, Peekskill, NY
Fully refundable
$139 nightly
The price is $159 total per night from Jul 3 to Jul 4
$159 total
Jul 3 - Jul 4
Total includes taxes and fees
9/10 Wonderful! (1,002 reviews)
"Beautiful waterfront walking path along the Hudson River"

Reviewed on Jun 27, 2025

Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG
The Abbey Inn & Spa
The Abbey Inn & Spa
4 out of 5
900 Fort Hill Rd, Peekskill, NY
Fully refundableReserve now, pay when you stay
$411 nightly
The price is $470 total per night from Jul 1 to Jul 2
$470 total
Jul 1 - Jul 2
Total includes taxes and fees
9.2/10 Wonderful! (183 reviews)
"We had a great stay at this property! The hotel is beautiful, with stunning grounds and a breathtaking view. Everything was exceptionally clean, and the staff were not only professional but also genuinely kind and helpful throughout our visit. The only downside was the lack of soundproofing—we could ..."

Reviewed on Jun 22, 2025

The Abbey Inn & Spa
See all 741 properties in Peekskill
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.

Find the Best Peekskill Vacation Packages

Peekskill Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Westchester County Airport (HPN)
Population
24,000
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Franklin D. Roosevelt State Park, Paramount Hudson Valley Theater and Jacob Burns Film Center Theater

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Frequently asked questions

How much does a Peekskill vacation package cost?
Offering excellent value package deals from $218 on Expedia, you'll be thrilled with how little a vacation to Peekskill costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Peekskill?
If you're hoping to snag a cheap Peekskill vacation package, consider planning a trip in June, November and December. You'll typically find better rates on flights and accommodations during these months --- ideal for travelers wishing to save money.
How many days is enough for Peekskill?
Allow at least 2 days for your Peekskill vacation to enjoy all that makes this destination unique. Explore key neighborhoods, including Montrose and Crompond. Then tick off top sights like Peekskill Landing Park and Charles Point Pier Park. With a well-organized itinerary, you can keep busy with room for some rest and relaxation too. Want to go beyond Peekskill? Consider fitting in an excursion or two.
Is it worth booking a vacation package to Peekskill?
Peekskill is a good vacation destination with attractions like Peekskill Landing Park among the many things to keep you busy. Whether you're heading away with the family or planning a trip with friends, a Peekskill vacation promises a good time for everyone.
How to find the best Peekskill package deals?
Start your search for a Peekskill package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Peekskill package deal straight away, simply tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Peekskill adventure off to a flying start.
Is it cheaper to book a Peekskill vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll usually land a better deal than booking each component separately. And you'll still get the freedom to create a customized Peekskill vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Peekskill?
If you're planning a spontaneous Peekskill getaway, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score awesome deals on your flights and hotels by booking well in advance.
How to plan a trip to Peekskill?

  1. Pick the best time to travel: Your schedule, favorite season and the type of weather you enjoy can all influence your decision on when to travel to Peekskill.
  2. Set your budget: Factor in costs such as flights, food and transportation when calculating how much to save for your trip to Peekskill. Then, select a hotel that matches your budget, whether that's an economical stay or a lavish retreat.
  3. Use our trip planning tool to explore Peekskill: Research every part of your trip to Peekskill with this comprehensive planner. Invite your family and friends to collaborate on a group trip, search for stays or things to do and make bookings.
  4. Decide how long to go for: Now that you're more familiar with Peekskill, you can figure out the right length of your vacation. Put together a draft itinerary and allocate enough time to get through everything on your must-do list.
  5. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a tailored Peekskill vacation package.
  6. Book activities and experiences in advance: Whether it's a ticket to a big attraction or a day trip in nature, you won't have to worry about missing out on the highlights of Peekskill. Find all the exciting things to do in Peekskill with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Peekskill vacation packages?
If you're anything like us, you love jet-setting around the world but are not a fan of the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Peekskill trip across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.