Peekskill Vacations from $631
Book a Hotel + Flight or Car together to unlock savings
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.
Luxury 3BR Family Home Game Room Parking
Bryn Mawr
$631
per person
Dec 11 - Dec 14
found 6 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to White Plains (HPN)
5.6/10 (4 reviews)
This location is fake, this is a scam, this location doesn’t exist, they stole my money. This is not a real location, please don’t fall for this and get scammed like we did. I have reported this.
Reviewed on Sep 18, 2026
Luxury NYC Home with Free Parking for 12
$881
per person
Dec 3 - Dec 8
found 11 hours ago
Roundtrip flight included
Miami (MIA) to White Plains (HPN)
2/10 (1 review)
Place didn't exist. Host did not respond to requests to clarify check-in. Upon arriving, the location was not as described and an individual who answered the door informed our party this was not a rental property. Had to last minute book elsewhere.
Reviewed on Feb 11, 2026
Modern Comfort in the Heart of NYC
Southeast Yonkers
$676
per person
Dec 11 - Dec 14
found 6 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to White Plains (HPN)
3.6/10 (4 reviews)
It took calling the booking website customer service to get in contact with the host. I end up getting a different property that the one I reserved but the new on was more bedrooms, at the end I work out but it took some long coy with the host.
Reviewed on Jun 29, 2026
Modern Luxury Home w GameRoom & Parking
Southeast Yonkers
$2,913
per person
Dec 13 - Dec 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
4.6/10 (11 reviews)
Though the privous occupants refused to vacate the property in time but the landlord was suupportive went out of their way and provided a refund option and an alternative...we took the alternative which happen to be better than the originally booked property ...
Will use this management and property owner in our upcoming short terms rentals.....
Reviewed on Sep 13, 2026
Stay near popular Peekskill attractions
Peekskill Landing Park
8.8/10 (53 reviews)
This revitalized Hudson River park showcases scenic boardwalks and a peaceful waterfront setting. Spot bald eagles while kayaking or enjoy the shoreline trails with panoramic river views.
Photo by Irishbelle30
Charles Point Pier Park
8.6/10 (44 reviews)
This historic Hudson River pier offers sweeping views of Bear Mountain and peaceful riverfront trails. Bring binoculars to spot eagles while enjoying a picnic along the scenic waterfront.
Dramatic Hall
This 1837 venue captivates with exposed brick walls and romantic lighting beneath vintage disco balls. Experience the historic charm during evening performances or book it for an unforgettable celebration.
Paramount Hudson Valley Theater
8.0/10 (24 reviews)
This historic Art Deco theater captivates with its original 2,000-bulb marquee and intimate 1,000-seat venue. Experience diverse performances from classical music to comedy shows in a space known for excellent acoustics.
Hudson Valley Center for Contemporary Art
7.2/10 (17 reviews)
This former factory houses cutting-edge contemporary art in spacious galleries. Explore thought-provoking exhibitions from emerging and established artists in a contemplative atmosphere.
Peekskill Museum
7.0/10 (14 reviews)
Housed in the historic Queen Anne-style Herrick House, the Peekskill Museum showcases local history through curated rooms. Volunteers share fascinating stories of Hudson Valley heritage.
Lincoln Depot Museum
7.2/10 (13 reviews)
This restored 19th-century depot commemorates Lincoln's 1861 pre-inaugural visit to Peekskill. Explore Civil War artifacts and interactive exhibits while enjoying scenic Hudson River views.
Depew Park
7.6/10 (18 reviews)
This 192-acre green space offers wooded trails and recreational facilities around Lake Mitchell. Enjoy swimming at Veterans Memorial Pool or unwind at the lakeside picnic pavilion after tennis.
Peekskill Hotel Deals
Inn on the Hudson
634 Main Street Peekskill NY
Fully refundableReserve now, pay when you stay
$109 nightly
$125 total
Oct 4 - Oct 5
Total with taxes and fees
The Abbey Inn & Spa
900 Fort Hill Rd Peekskill NY
$469 nightly
$537 total
Sep 30 - Oct 1
Total with taxes and fees
Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG
2 John Walsh Boulevard Peekskill NY
Fully refundable
$157 nightly
$180 total
Oct 7 - Oct 8
Total with taxes and fees
9.2/10 Wonderful! (1,001 reviews)
"Great"
Reviewed on Sep 25, 2026
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 $631 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?
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.