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Peekskill vacation rentals

We found 148 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in Peekskill that are perfect for your trip. Whether you're traveling with family, friends, or just your furry companion, vacation homes have the best amenities for spending time at your vacation home, which might include WiFi and a pool. No matter what you're looking for, you're sure to find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

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Find out more about Peekskill

Why visit Peekskill

  • Scenic Hudson River Views: Enjoy breathtaking vistas of the Hudson River, perfect for photography and relaxation.
  • Outdoor Activities: Engage in hiking, biking, and picnicking in nearby parks, catering to nature lovers and families alike.
  • Rich Cultural Scene: Explore art centers and cultural events that showcase local talent and community spirit.
  • Charming Downtown: Stroll through a quaint downtown filled with shops, restaurants, and historical architecture.
  • Diverse Accommodations: Choose from a variety of vacation rentals, ensuring a comfortable and memorable stay.

Popular types of accommodation in Peekskill

Planning a getaway to Peekskill? You're in for a treat. Discover a variety of vacation rentals, from cozy private homes and charming cottages to modern apartments and luxurious guest suites. Whether you're seeking a family-friendly home rental or a stylish apartment in the heart of the city, Peekskill offers the perfect accommodation options to make your stay unforgettable. Start your adventure by exploring the best Peekskill rentals today.

  • Houses: The top choice for visitors in Peekskill, these homes offer ample space and comfort, perfect for families or groups.
  • Apartments: A convenient option for travelers seeking a home-like atmosphere while enjoying the city.
  • Cottages: These quaint, charming retreats provide a cozy escape in the heart of nature.
  • Cabins: Ideal for those wanting a rustic getaway, blending comfort with the great outdoors.
  • Condos: A modern choice that combines style and convenience, often located in prime areas.**

Top attractions near Peekskill

Peekskill, New York, is a perfect destination for family, outdoor, and city-themed vacations. Visitors can explore a variety of attractions, including national and urban parks, as well as arts centers. With its rich cultural offerings and outdoor experiences, Peekskill caters to travelers seeking a blend of adventure and family-friendly fun. Enjoy everything this charming city has to offer during your visit.

  • Bear Mountain State Park: Located 4 miles from Peekskill, this expansive park offers breathtaking scenery, numerous hiking trails, and a variety of outdoor activities, making it perfect for adventure seekers and nature lovers alike.
  • United States Military Academy: Situated 7 miles away, this prestigious military academy is rich in history and tradition, providing visitors with a glimpse into the training of future leaders of the U.S. Army.
  • Van Cortlandt Manor: Also 7 miles from Peekskill, this historic estate immerses visitors in rich culture and heritage, showcasing beautifully preserved architecture and gardens that reflect the area's colonial past.

Things to do recommended for couples

If you're seeking a romantic getaway in Peekskill, consider catching a show at the Tarrytown Music Hall for entertainment vibes. For a luxurious experience, visit the Golf Club at Mansion Ridge. Don't forget to savor wine together at Palaia Vineyards Winery, where romance fills the air.

Things to do recommended for families

Families visiting Peekskill can relax at Peekskill Landing Park, enjoy thrilling races at Michie Stadium just 7 miles away, and experience adventure at Grand Prix New York / Spins Bowl located 11 miles from the city. It's the perfect blend of relaxation and excitement for everyone.

Things to do recommended for groups

Shop till you drop at Woodbury Common Premium Outlets, just 11 miles away, enjoy a show at the Paramount Hudson Valley Theater in Peekskill, or hit the links at Garrison Golf Club, located 7 miles away, for a fun day of sports and outdoor activities with your group.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Peekskill

If you’re traveling with a group, family, or pets, or planning an extended stay, be sure to use the appropriate filters to match your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Peekskill with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Peekskill with young kids: Traveling with little ones can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Peekskill: For many families, a vacation isn’t truly fulfilling without their furry companions. If that resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Peekskill: If you're in search of vacation rentals that offer discounts for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like parking, a spacious kitchen, or a private pool in your search for the perfect getaway.

Where to stay near Peekskill

Peekskill, New York, offers a delightful mix of family-friendly activities and scenic views, making it an ideal vacation spot. Explore its charming downtown, enjoy outdoor excursions, and take in the rustic beauty of the Hudson River. Nearby cities add to the experience with romantic atmospheres and budget-friendly options. Whether you're seeking sweeping views or a friendly community, Peekskill promises a memorable getaway for everyone.

  • Cortlandt: Located a mere 2 miles from Peekskill, Cortlandt is a charming city that beckons outdoor enthusiasts and families alike. Known for its scenic beauty, visitors can enjoy lush parks, walking trails, and stunning views of nearby lakes. Cortlandt is home to several engaging venues, including an arts center and a bustling shopping area. The area's rich history is highlighted by local landmarks and national state parks, making it an ideal spot for both relaxation and exploration.
  • Hudson River Valley: Just 2 miles away from Peekskill, the Hudson River Valley offers a breathtaking natural landscape that is perfect for outdoor adventures and romantic getaways. This picturesque valley is characterized by its stunning lakes, majestic mountains, and winding rivers, providing an incredible backdrop for hiking, skiing, and leisurely strolls. With shopping areas and ski fields nearby, visitors can enjoy a blend of excitement and relaxation while soaking in the area's natural beauty.
  • Buchanan: Also located 2 miles from Peekskill, Buchanan is a welcoming city known for its family-friendly atmosphere and outdoor experiences. Surrounded by beautiful lakes and mountains, it offers ample opportunities for recreation and exploration. Visitors can engage in activities at local educational centers, enjoy a round of golf at a country private club, or explore the vibrant shopping area. Buchanan is a fantastic destination for those looking to connect with nature while enjoying the comforts of a friendly community.

Best time to go to Peekskill

If you're planning a trip to Peekskill, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April, July and September, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January28.9°F (-1.7°C)Light RainMostly SunnySlightly LowSlightly Low
February30.9°F (-0.6°C)Light RainMostly SunnyAverageSlightly Low
March38.3°F (3.5°C)Light RainMostly SunnyAverageSlightly Low
April49.6°F (9.8°C)Light RainMostly SunnySlightly HighAverage
May60.1°F (15.6°C)Light RainMostly SunnyAverageSlightly High
June68.5°F (20.3°C)Light RainMostly SunnyAverageAverage
July75.0°F (23.9°C)Light RainMostly SunnySlightly HighSlightly High
August73.2°F (22.9°C)Light RainMostly SunnyAverageSlightly High
September66.0°F (18.9°C)Light RainMostly SunnySlightly HighAverage
October55.0°F (12.8°C)Light RainMostly SunnyAverageAverage
November43.2°F (6.2°C)Light RainMostly SunnySlightly LowAverage
December35.2°F (1.8°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Also, planning a longer stay can often lead to significant savings. To discover the ideal Vrbo property that fits your budget, use our filters to refine your search by price, location, and type of vacation rental.

Save more with One Key

Reserve an eligible Vrbo for your group getaway and earn OneKeyCash on your entire booking. Being the planner definitely has its perks. When you join our travel rewards program, One Key, you'll gain access to exclusive member discounts and earn OneKeyCash on qualifying reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning made easy

Introducing Vrbo's user-friendly Trip Board, where you can easily plan new trips, pick up right where you left off, and manage your travel plans with ease. You can find all the properties you've saved or booked in the Potential, Upcoming, or Current Trips sections. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

The riverside setting of Peekskill is ready to explore

The riverfront and mountains create a pretty picture of Peekskill. This welcoming and relaxing city entices travelers with its hiking and restaurants. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Peekskill

Are you looking for things to do while you're in the area? Venture out of your cozy vacation rental and experience everything that makes Peekskill a fun place to get away. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Putnam County Golf Course (10.8 mi / 17.4 km)
  • Brotherhood Winery (16.3 mi / 26.2 km)
  • Patriot Hills Golf Club (7.2 mi / 11.7 km)
  • Hilltop Hanover Farm and Environmental Center (7.8 mi / 12.6 km)
  • Rockland Lake State Park Championship Golf Course (9.2 mi / 14.8 km)
  • Rockland Bakery (13.5 mi / 21.7 km)

Exploring the natural features in Peekskill

Travelers enjoy Peekskill for its riverfront and mountain views. Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, you'll be sure to find the perfect setting for your vacation in Peekskill. These are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city center:

  • Croton Point Park (7.2 mi / 11.6 km)
  • Lake Welch Beach (8.8 mi / 14.1 km)
  • Boscobel House and Gardens (8.9 mi / 14.4 km)
  • Storm King State Park (10.3 mi / 16.6 km)
  • Rockland Lake State Park (10.7 mi / 17.2 km)
  • Hudson Highlands State Park (11 mi / 17.6 km)

How to get to and around Peekskill

The nearest airport is in Stewart Intl. Airport (SWF), located 17.2 mi (27.8 km) from the city center. If you can't find a flight that's convenient for your trip, you could book a flight to Westchester County Airport (HPN), which is 18.6 mi (29.9 km) away.

If you're traveling by train, the main station serving the city is Peekskill.

Frequently asked questions

What is the best area to stay in Peekskill, New York, United States of America when booking a vacation rental?
When looking for the best area to stay in Peekskill, New York, a great choice would be along the waterfront. This neighborhood offers stunning views of the Hudson River and is great for those who appreciate scenic beauty and outdoor activities. Here, you can explore the picturesque riverfront parks, which provide lovely walking paths and picnic spots, making it ideal for families and couples alike.

Another appealing area is the downtown district, known for its vibrant arts scene and charming atmosphere. This neighborhood is home to a variety of boutiques, cafes, and restaurants, giving visitors a taste of local culture and cuisine. In addition, the nearby Paramount Hudson Valley Theater frequently features live performances, adding to the lively ambiance.

In terms of vacation rentals, Peekskill has a diverse selection, with many properties available in both the waterfront and downtown areas. This variety ensures that you can find accommodations that suit your needs, whether you're looking for a cozy apartment or a larger home.
How much does it cost to rent a vacation home in Peekskill?
Prices for vacation rentals in Peekskill vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Peekskill to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Peekskill vacation house rentals?
You can find great discounts on house rentals in Peekskill on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of vacation rental accomodation in Peekskill?
In Peekskill, vacation houses are the most popular type of rental accommodation, with several available throughout the area. These homes typically offer spacious layouts, featuring multiple bedrooms, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups. Many of these properties come with outdoor spaces, such as patios or gardens, that allow guests to enjoy the scenic views of the Hudson River and the nearby parks.
Are there any family house rentals in Peekskill?
In Peekskill, New York, there are several family-friendly house rentals available. This charming city, located along the Hudson River, offers a variety of properties that cater to families. Many homes feature spacious living areas, well-equipped kitchens great for family meals, and outdoor spaces where children can play and explore.

The neighborhood is close to local parks, such as Riverfront Green Park, which provides playgrounds, picnic areas, and scenic walking paths along the waterfront. Additionally, families can enjoy nearby cultural attractions, including the Peekskill Museum and the vibrant arts scene in the downtown area.
Can I find long-stay vacation rentals in Peekskill?
A long-stay vacation rental in Peekskill is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Peekskill?
In Peekskill, travelers can find several pet-friendly house rentals that cater to both comfort and convenience. Many of these homes offer amenities such as spacious backyards, fully equipped kitchens, and cozy living areas, making them suitable for families or groups traveling with pets.

The area is known for its scenic views along the Hudson River, providing opportunities for outdoor activities. Nearby parks, such as the Peekskill Riverfront Green Park, feature walking trails and open spaces that are great for pet owners to enjoy time outdoors with their furry friends. Additionally, the charming downtown area offers pet-friendly cafes and shops, enhancing the overall experience for those traveling with pets.
Are there any remote work vacation rentals in Peekskill?
In Peekskill, New York, there are several vacation rentals that cater to remote work needs. Many of these properties come equipped with essential amenities such as high-speed Wi-Fi, dedicated workspaces with desks and chairs, and comfortable living areas that allow for a productive work environment. Travelers can expect to find rentals that not only support remote work but also provide a cozy atmosphere for relaxation after a busy day.

The town itself offers a charming mix of historic sites and natural beauty, with access to the Hudson River waterfront, local parks, and vibrant cultural attractions. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Peekskill vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Peekskill with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Peekskill?
In Peekskill, popular rental amenities include features that enhance comfort and convenience for travelers. Many vacation rentals offer onsite parking, making it easy for guests to arrive and explore the area without worrying about street parking. Air conditioning is a common amenity, ensuring a pleasant indoor environment, especially during warmer months. Additionally, most rentals come equipped with a desk and desk chair, suiting those who may need to work or study during their stay. A coffee and tea maker is also frequently available, allowing guests to enjoy a warm beverage at their leisure.
When is the best time to visit Peekskill for a vacation rental?
The best time to visit Peekskill for a vacation rental is during the peak season from July to September. This vibrant period attracts travelers eager to explore the Hudson Valley, where the charming riverside town offers a delightful mix of outdoor adventures and cultural experiences. With warm temperatures averaging in the mid-70s to low 80s Fahrenheit, it's an ideal time for hiking the scenic trails, enjoying the local art scene, or indulging in delicious dining options along the Hudson River.

July, in particular, is the most popular month to visit Peekskill. During this time, you can immerse yourself in a lively option as festivals and outdoor events bring the community together. The summer months also provide ample opportunities for boating, fishing, and enjoying the picturesque waterfront, making it a great choice for families and groups looking for activities.

For those seeking a more budget-friendly experience, consider planning your trip in December. While this month falls outside the bustling tourist season, it offers a unique charm with holiday decorations and a cozy atmosphere. You can enjoy quiet strolls along the river and explore local shops without the crowds.
How early should I book a Peekskill vacation rental?
Book your Peekskill vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Peekskill, New York, United States of America?
In Peekskill, visitors can enjoy a variety of attractions that highlight the area's natural beauty and artistic vibe. The waterfront along the Hudson River offers picturesque views and opportunities for leisure activities, such as walking or biking along the Riverfront Green Park, which features playgrounds and picnic areas.

Art enthusiasts can explore the Peekskill Art Lofts and the nearby Hudson Valley Center for Contemporary Art, showcasing local and regional artists' work. The historic downtown area is home to charming shops, cafes, and restaurants, making it a pleasant spot for a leisurely stroll.

Additionally, the nearby Bear Mountain State Park provides outdoor enthusiasts with hiking trails, scenic vistas, and picnic spots, ideal for those who enjoy nature.
Can I change or cancel my Peekskill home rental booking on Vrbo?
To find Peekskill vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Peekskill vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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