A calm lake with a forested island in the distance, a picnic area, and a rocky shoreline.

Peekskill Vacations from $395

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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.
  • Jan 20 - Jan 24

    Newark Hansbury Multi Level House + Flight

    Weequahic
    4 nights
    2.0 star property
    6.8/10 - (5 reviews)
    "nice"
    Reviewed September 10, 2026
    Roundtrip • Atlanta (ATL) - New York (JFK)
    ATL - EWR • Nonstop LGA - ATL • Nonstop
    $665
    $395
    per traveler
    found 12 hours ago
    Newark Hansbury Multi Level House
  • Jan 7 - Jan 13

    INNSiDE by Meliá New York Nomad + Flight

    Manhattan
    6 nights
    4.5 star property
    9.2/10 - Wonderful (2,368 reviews)
    Roundtrip • Atlanta (ATL) - New York (JFK)
    ATL - JFK • Nonstop JFK - ATL • Nonstop
    Save 100% on your flight
    $1,545
    $781
    per traveler
    found 1 day ago
    INNSiDE by Meliá New York Nomad
  • Jan 20 - Jan 24

    JW Marriott Essex House New York + Flight

    Manhattan
    4 nights
    4.5 star property
    8.8/10 - Excellent (1,000 reviews)
    Roundtrip • Atlanta (ATL) - New York (JFK)
    ATL - JFK • Nonstop JFK - ATL • Nonstop
    $1,724
    $991
    per traveler
    found 1 day ago
    JW Marriott Essex House New York
  • Jan 7 - Jan 13

    The St. Regis New York + Flight

    Manhattan
    6 nights
    5.0 star property
    9.2/10 - Wonderful (294 reviews)
    Roundtrip • Atlanta (ATL) - New York (JFK)
    ATL - JFK • Nonstop JFK - ATL • Nonstop
    Save 100% on your flight
    $4,089
    $2,398
    per traveler
    found 1 day ago
    The St. Regis New York
  • Jan 7 - Jan 13

    Hotel St. James + Flight

    Manhattan
    6 nights
    3.0 star property
    8.8/10 - Excellent (8,171 reviews)
    Roundtrip • Atlanta (ATL) - New York (JFK)
    ATL - JFK • Nonstop JFK - ATL • Nonstop
    $946
    $562
    per traveler
    found 1 day ago
    Hotel St. James

Where to stay near Peekskill

Explore the charm of Central Peekskill, a perfect base for your Hudson Valley adventure. Enjoy family-friendly outdoor activities and picturesque scenery, making it an ideal fall getaway. Experience the warm atmosphere and vibrant culture that make this city a delightful destination for all travelers.

Hudson River Valley

For travelers seeking a memorable trip, the Hudson River Valley offers a perfect blend of nature and culture just about 2 miles from Peekskill. This stunning area is ideal for those who appreciate the great outdoors, with highlights such as Bear Mountain State Park and Blue Mountain Reservation for hiking and skiing adventures. The historic charm of Van Cortlandt Manor adds to the experience, making it a romantic weekend getaway. Hudson River Valley is a wise choice for hotel bookings, ensuring easy access to these captivating attractions.

Cortlandt

Plan your stay in Cortlandt, a top-rated choice for outdoor enthusiasts and families eager to explore the breathtaking Bear Mountain State Park, the historic Van Cortlandt Manor, and the serene Blue Mountain Reservation. This vibrant city offers a mix of adventure and relaxation, making it a perfect home base for experiencing the natural beauty and rich history of the region. Located about 2 miles from Peekskill, Cortlandt is an excellent choice for your vacation, ensuring easy access to all the excitement nearby.

Buchanan

If you are a nature-loving family or a couple seeking a romantic getaway, look no further than Buchanan, which features stunning outdoor spaces like Bear Mountain State Park and Blue Mountain Reservation, perfect for hiking and enjoying scenic views. Visitors can also explore the historic charm of Van Cortlandt Manor or relax at the local beaches. Located about 2 miles from Peekskill, Buchanan offers an ideal base for your New York adventure, making it a smart choice for your stay.

Montrose

Montrose stands out as a prime spot for travelers seeking a weekend getaway or family adventure in New York. This charming city offers easy access to stunning natural landscapes at Bear Mountain State Park and Blue Mountain Reservation, alongside the historic allure of Van Cortlandt Manor. With its inviting parks and shopping areas, Montrose provides a delightful blend of outdoor and urban experiences. Located about 2 miles from Peekskill, it’s a smart choice for those wanting to explore the Hudson Valley.

Bear Mountain

Travelers seeking a family-friendly escape will find Bear Mountain to be the ideal base for their vacation, featuring breathtaking landscapes and outdoor adventures. With attractions like Bear Mountain State Park for hiking and picnicking, the West Point Museum for a glimpse into military history, and the scenic Monteverde at Oldstone for dining, there's something for everyone. Located about 5 miles by car from Peekskill, Bear Mountain offers a seamless travel experience that makes it a smart choice for your stay.

Discover the most popular places to visit in Peekskill

Peekskill Hotel Deals

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

What's included in a Peekskill vacation package?

A Peekskill vacation package lets you combine round-trip flights, hotel stays, and rental cars. Many hotels in Peekskill offer free breakfast, which can be a convenient way to start your day. Travelers flying into the area often use John F. Kennedy International Airport (JFK), Newark Liberty International Airport (EWR), or LaGuardia Airport (LGA) for their trips.


Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.

How can I save money on a Peekskill vacation package?

When you bundle, you can save up to 30%*. To save money on a Peekskill package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

What's the best vacation package for Peekskill?

For families, a Peekskill vacation package built around a stay at Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG is a strong choice. This hotel, rated 8.9 out of 10, offers family rooms and an indoor pool, with travelers often praising the accommodating staff and spacious rooms.


Couples seeking a more luxurious or romantic escape might consider a Peekskill vacation package featuring The Abbey Inn & Spa. This 4-star property, also rated 8.9 out of 10, provides a spa, outdoor pool, and a bar/lounge, and travelers frequently highlight the excellent food and breathtaking overall experience.


If you're looking for a great value, a Peekskill vacation package with a stay at Inn on the Hudson could be ideal. This hotel, praised for its good value and spacious rooms, includes free breakfast and is pet friendly, with travelers often noting the amazing staff.

Is Peekskill better suited for a beach vacation or a cultural trip?

Peekskill is primarily a cultural destination, offering a rich history and a vibrant arts scene for your Peekskill vacation.


Its historical roots trace back to Henry Hudson's exploration of the Hudson River, and the city's name itself comes from early Dutch settlers. For arts, the Paramount Hudson Valley Theater offers live performances, while the Hudson Valley Museum of Contemporary Art showcases modern works.


Beyond culture, a Peekskill vacation package also provides access to outdoor activities, with places like Bear Mountain State Park about 8 miles away.

What are the top things to do in Peekskill?

A Peekskill vacation brings together historical sites, cultural venues, and outdoor recreation:


Browse and book things to do in Peekskill on Expedia.

Do you need to rent a car in Peekskill, or is public transport enough?

While public transport is available for your Peekskill vacation packages with flights, a rental car offers more flexibility for exploring the wider region.


Peekskill has local bus service and commuter rail service to New York City. However, many of the area's attractions, such as Bear Mountain State Park about 8 miles away and the United States Military Academy about 10 miles away, are best reached by car. A rental car allows you to easily visit these sites and other destinations beyond the immediate city center during your Peekskill vacation package.

Are Peekskill vacation package hotels conveniently located?

Peekskill vacation package hotels are generally conveniently located, with many options within easy reach of the city center.


For example, Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG and The Abbey Inn & Spa are both about 1 mile from central Peekskill. For an even closer stay, Inn on the Hudson is about a 15-minute walk from the heart of the city.


This central positioning allows for easy access to local attractions and amenities during your stay.

Are there vacation package hotels in Peekskill within walking distance of restaurants and shops?

Central Peekskill vacation package hotels often place restaurants and shops within walking distance.


Inn on the Hudson is about a 15-minute walk from central Peekskill, putting you close to local dining and retail. Both Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG and The Abbey Inn & Spa are about 1 mile from the city center, offering convenient access to the area's amenities.


When choosing your hotel, consider checking the map for specific walking routes to your preferred spots.

Can I change or cancel my Peekskill vacation package if my plans change?

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Do One Key members get extra savings when booking Peekskill vacation packages?

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Does Expedia offer Book Now, Pay Later Peekskill vacation packages?

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Peekskill vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

How do I find last-minute vacation packages to Peekskill?

To find last-minute vacation packages to Peekskill, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

How does free cancellation work on Peekskill vacation packages?

Free cancellation on a Peekskill vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Is it cheaper to book a Peekskill vacation as a package or separately?

Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Peekskill getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Why should I book my Peekskill vacation package with Expedia?

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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