Peekskill holiday lettings

We found 125 holiday rentals — enter your dates for availability

Discover a selection of holiday rentals in Peekskill that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday homes have the best amenities for spending time at your holiday home, which might include a garden and pool. Whatever you're looking for, you'll be sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.

Find spaces that suit your style

Why visit Peekskill

  • Scenic Outdoor Activities: Enjoy the beauty of urban parks and national state parks, perfect for hiking, picnicking, and family outings.
  • Arts and Culture: Immerse yourself in the vibrant arts community with galleries and cultural events showcasing local talent.
  • Charming Downtown: Stroll through the bustling downtown area, filled with unique shops, cafés, and restaurants.
  • Romantic Atmosphere: Discover the quaint South Side, ideal for romantic outings or budget-friendly adventures.
  • Comfortable Accommodation: Choose from a variety of delightful holiday rentals, ensuring a cosy stay in Peekskill.

Popular types of accommodation in Peekskill

Vrbo offers a fantastic selection of vacation rentals in Peekskill, perfect for your getaway. Whether you're seeking a private vacation home, a cosy apartment in Peekskill, or a charming cottage, we have options to suit every traveler's needs. Our visitors often choose from delightful home rentals or spacious house rentals, ensuring a comfortable stay while exploring this vibrant area. Discover the ideal accommodation for your next adventure!

  • Houses: The top choice for holidaymakers in Peekskill, offering spacious, comfortable living for families or groups.
  • Apartments: A popular option for couples or solo travellers, providing a convenient and self-contained stay.
  • Cottages: Charming and quaint, these rentals offer a cosy retreat amidst scenic surroundings.
  • Cabins: Ideal for those seeking a rustic experience, nestled in nature for a tranquil escape.
  • Condos: Modern and well-equipped, these accommodations cater to those looking for a stylish getaway.**

Top attractions near Peekskill

Pekskill offers a delightful blend of family-friendly activities, outdoor adventures, and vibrant urban experiences. Visitors can explore local attractions such as urban parks, national state parks, and arts centres, providing rich cultural and recreational opportunities. Whether you're on a day out with the family or seeking a relaxing getaway, there's plenty to see and do in and around Peekskill to enhance your holiday experience.

  • Bear Mountain State Park: Located 2.5km from Peekskill, this stunning national park offers a plethora of outdoor adventures, including hiking trails, picturesque scenery, and breathtaking views of the Hudson River. It’s an ideal spot for nature enthusiasts and families looking to explore the great outdoors.
  • United States Military Academy: Situated 4.3km away, this prestigious military academy is steeped in history and tradition. Visitors can explore the beautiful campus, learn about the academy's role in American history, and appreciate its impressive architecture.
  • Van Cortlandt Manor: Just 4.3km from Peekskill, this historic house offers a glimpse into colonial life with its meticulously preserved architecture and beautiful gardens, providing a rich cultural experience for history buffs and visitors alike.

Things to do recommended for couples

For a romantic getaway in Peekskill, consider a concert at Tarrytown Music Hall, just 9.3km away, or indulge in wine tasting at Palaia Vineyards Winery, 6.8km from town. For a touch of luxury, visit The Golf Club at Mansion Ridge, located 8.7km away.

Things to do recommended for families

During your family vacation in Peekskill, enjoy the serene atmosphere at Peekskill Landing Park, experience the excitement of Michie Stadium just 4.3km away, and embark on an adventurous day at Grand Prix New York / Spins Bowl, located 6.8km from Peekskill for some thrilling karting fun.

Things to do recommended for groups

Groups visiting Peekskill can enjoy a shopping spree at Woodbury Common Premium Outlets, indulge in a show at the Paramount Hudson Valley Theater, or tee off at the nearby Mohansic Golf Course for some outdoor fun and sports activities.

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

If you're planning a trip with a group, family, pets, or seeking extended stays, it's important to filter your options according to your key preferences. Here are some helpful booking tips for Vrbo.

  • Traveling to Peekskill with a group: Think about how many bedrooms you require, as well as additional features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Peekskill with young kids: Traveling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, as well as provide 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 holiday isn’t truly fulfilled without their furry companion by their side. If that resonates with you, explore Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Peekskill: If you’re seeking holiday rentals with discounts for stays of a month or more, you’ve come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Peekskill

Peekskill, New York, offers a delightful blend of family-friendly excursions and vibrant city life. Visitors can explore the artsy community, enjoy the bustling downtown, and take leisurely drives through the picturesque surroundings. Just a short jaunt away, the South Side presents a charming atmosphere perfect for romantic outings or budget-friendly adventures. With friendly locals and a welcoming vibe, Peekskill promises an unforgettable experience for every type of traveller.

  • Cortlandt: Nestled a mere 1.2km from Peekskill, Cortlandt is an inviting city that offers a splendid blend of outdoor activities and family-friendly experiences. Here, you can explore the scenic beauty of local lakes and historic sites, making it an ideal spot for nature lovers and history buffs alike. The area boasts an arts centre and shopping options, ensuring that visitors have a variety of entertainment and cultural experiences at their fingertips. With its picturesque landscapes and tranquil parks, Cortlandt is perfect for a leisurely day out with loved ones.
  • Hudson River Valley: Just 1.2km away from Peekskill, the Hudson River Valley is renowned for its breathtaking natural scenery and romantic ambiance. This stunning valley is a haven for outdoor enthusiasts, offering activities such as skiing and vibrant shopping areas. Visitors can revel in the beauty of the local lakes, majestic mountains, and the winding river that defines this region. Whether you’re taking a scenic hike or enjoying a leisurely stroll along the riverbanks, the Hudson River Valley promises a truly enchanting experience.
  • Buchanan: Located only 1.2km from Peekskill, Buchanan is a charming city that invites families and outdoor enthusiasts to explore its natural wonders. The area features lovely lakes and mountains, complemented by the nearby national state park, providing ample opportunities for hiking and picnicking. Buchanan is also home to excellent educational facilities and golf courses, catering to a variety of interests. This welcoming city is perfect for a fun-filled day with family or a peaceful retreat in nature.

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 SunnyAverageAverage
June68.5°F (20.3°C)Light RainMostly SunnyAverageSlightly High
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 a breeze

Are you hoping to cut costs on your upcoming holiday? It may be worth considering some flexibility with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Vrbo accommodation that fits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board offers a handy platform for you to plan new adventures, resume your previous arrangements, or manage your itinerary with ease. You can view your saved or booked properties neatly organised under Potential, Upcoming, or Current Trips. To begin making the most of Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

The riverfront setting of Peekskill is ready to explore

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

Activities and attractions in Peekskill

Are you hoping to discover attractions to see during your stay? Venture out of your holiday home and experience everything that makes Peekskill a fun place to get away to. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Putnam County Golf Course (10.8 mi / 17.4 km)
  • Brotherhood Winery (16.3 mi / 26.2 km)
  • Black Mountain (7.2 mi / 11.6 km)
  • Hilltop Hanover Farm and Environmental Center (7.8 mi / 12.6 km)
  • West Point Golf Course (8.2 mi / 13.2 km)
  • Rockland Lake State Park Championship Golf Course (9.2 mi / 14.8 km)

Exploring the natural features in Peekskill

Travellers enjoy Peekskill for its riverfront and mountain views. Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Peekskill is a great place to get outside. Here are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Blue Mountain Reservation (1.2 mi / 1.9 km)
  • Croton Point Park (7.2 mi / 11.6 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)
  • Lake Mahopac (11.3 mi / 18.2 km)

How to get to and around Peekskill

The nearest airport is in Newburgh, NY (SWF-Stewart Intl.), located 17.2 mi (27.8 km) from the city centre. If you can't find a flight that's convenient for your trip, you might consider flying into White Plains, NY (HPN-Westchester County), which is 18.6 mi (29.9 km) away.

If you prefer train travel, the main station is Peekskill.

Frequently asked questions

What is the best area to stay in Peekskill when booking a holiday rental?
When booking a holiday rental in Peekskill, New York, a fantastic area to consider is the waterfront district. This charming neighbourhood offers a delightful blend of scenic views and vibrant local culture. Staying here places you right by the Hudson River, where you can enjoy leisurely strolls along the riverfront promenade or engage in various outdoor activities. A highlight in this area is the Peekskill Riverfront Green Park, which hosts events and provides a lovely space for picnics and relaxation.

Another excellent option is the downtown area, characterised by its historic buildings and a lot of dining and shopping options. This bustling part of Peekskill is home to attractions like the Paramount Hudson Valley Theatre, where you can catch live performances and cultural events. The downtown area typically features a variety of holiday rental properties, offering everything from quaint apartments to more spacious homes.
How much does it cost to rent a holiday home in Peekskill?
Prices for holiday 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 holiday 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 holiday rental accomodation in Peekskill?
In Peekskill, holiday 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 outdoor spaces such as patios or gardens, allowing guests to enjoy the scenic views of the Hudson River. The properties are often situated in quiet neighbourhoods, making them an ideal choice for families or groups looking for a comfortable and relaxing stay.
Are there any family house rentals in Peekskill?
In Peekskill, New York, there are several family-friendly house rentals available, providing an excellent base for exploring the area. The locale features spacious homes with amenities that cater to families, including full kitchens, ample living spaces for gatherings, and outdoor areas where children can play safely. Some properties even boast backyards with BBQ facilities, making it easy to enjoy alfresco dining.

This charming town is situated near the banks of the Hudson River, offering picturesque views and opportunities for outdoor activities. Families can explore nearby parks, such as the scenic Riverfront Green Park, which has playgrounds and walking trails. Additionally, the Peekskill Museum and local art galleries provide cultural experiences that can be enjoyable for all ages.
Can I find long-stay holiday rentals in Peekskill?
A long-stay holiday rental in Peekskill is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Peekskill?
In Peekskill, several pet-friendly house rentals are available, offering a comfortable and inclusive setting for travellers and their furry companions. Many of these rentals come equipped with modern amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces like patios or gardens, which are ideal for pet owners.
Are there any remote work holiday rentals in Peekskill?
In Peekskill, New York, there are several remote work holiday rentals available, making it an ideal spot for those looking to combine work with leisure. Many of these properties are equipped with dedicated workspaces, including desks and comfortable desk chairs, ensuring a productive environment. High-speed Wi-Fi is commonly provided, allowing for seamless connectivity during your stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Peekskill holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Peekskill with parking available—perfect for families or travellers 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 complimentary Wi-Fi, coffee makers, cookware and dishware for self-catering, microwaves, and onsite parking options through third-party services. These amenities cater to the needs of travellers looking for convenience and comfort while exploring the area's attractions, such as the scenic Hudson River waterfront and the vibrant arts scene.
When is the best time to visit Peekskill for a holiday rental?
The peak season for holiday rentals in Peekskill runs from July to September, when the area comes alive with vibrant outdoor activities and events. This is an ideal time for travellers looking to enjoy the scenic beauty of the Hudson River Valley, with warm summer temperatures averaging around 25°C. Visitors can partake in a variety of activities, such as hiking in nearby parks, exploring local art galleries, or strolling along the picturesque waterfront.

July is particularly popular for those seeking a lively atmosphere, as it hosts numerous festivals and concerts that appeal to both families and adventure enthusiasts. The pleasant weather encourages outdoor dining, picnics, and leisurely walks, making it a superb time for both relaxation and exploration.

For those looking for a more budget-friendly option, December presents a unique charm with lower rental prices. While the weather can be cooler, hovering around 2°C, the festive season offers a delightful experience with holiday decorations, local events, and opportunities for winter walks along the river.
How early should I book a Peekskill holiday rental?
Book your Peekskill holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Peekskill?
In Peekskill, visitors can enjoy a variety of attractions that showcase the area's natural beauty and rich history. The waterfront along the Hudson River features scenic parks like Riverfront Green Park, which offers walking trails, picnic areas, and beautiful views of the river, making it a superb spot for leisurely strolls.

The Peekskill Museum, located in the heart of the city, provides insights into the local history and culture, while the nearby Paramount Hudson Valley Theatre hosts an array of performances and events, adding to the vibrant arts scene.
Can I change or cancel my Peekskill home rental booking on Vrbo?
To find Peekskill holiday 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 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 travellers 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 cosy cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, 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 organising 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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