Photo by Eugenio Ruiz

Peekskill vacation rentals

We found 131 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.

Vacation rentals with weekly discounts - Peekskill

Showing deals for:Nov 14 - Nov 21

Image gallery for Hudson River Valley Estate - New Listing!

Terrace/patio
10 out of 10 rating
Exceptional
(7 reviews)

Hudson River Valley Estate - New Listing!

Verplanck, NY

14% off
Price is CA $1,766
CA $15,442 total
includes taxes & fees
Hudson River Valley Estate - New Listing!

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Find out more about Peekskill

Find out more about Peekskill

Why visit Peekskill

  1. Outdoor Adventures: Enjoy scenic biking and hiking along the Hudson River and in nearby parks.
  2. Cultural Experiences: Explore local arts centres that showcase Peekskill's vibrant creative community.
  3. Charming Neighbourhoods: Stroll through inviting local areas filled with unique shops and dining options.
  4. Family-Friendly Activities: Discover budget-friendly excursions perfect for visitors of all ages.
  5. Welcoming Community: Experience the friendly atmosphere and hospitality from the locals.

Popular types of accommodation in Peekskill

Explore the charming vacation rentals in Peekskill, NY, where you'll find a variety of options to suit every traveler's needs. From houses to cozy apartments and delightful cottages, there's something for everyone. Whether you're searching for Peekskill apartments or rental locations, our platform offers transparent information and savings to ensure a worry-free stay. Discover your perfect getaway in this beautiful Hudson River town today!

  • Houses: The top choice for visitors in Peekskill, these homes offer a comfortable and spacious stay, perfect for families or groups.
  • Apartments: A popular option for those seeking a cozy and functional space, ideal for couples or solo travellers.
  • Cottages: Charming and quaint, these rentals provide a delightful escape with a touch of rustic charm.
  • Cabins: Great for nature lovers, these accommodations offer a warm retreat amidst the beautiful surroundings.
  • Villas: Luxurious and spacious, villas in Peekskill are perfect for those looking for an upscale experience.**

Top attractions in Peekskill

Pekskill, New York, is perfect for family, outdoor, and city-themed vacations. Visitors can enjoy a variety of attractions, including national and urban parks, as well as arts centres that provide rich cultural experiences. Whether you're seeking outdoor adventures or family-friendly activities, Peekskill has something for everyone. Don't forget to rent bikes to explore the scenic surroundings and make the most of your visit!

  1. Bear Mountain State Park: This stunning park, located 6.4km from Peekskill, offers breathtaking scenery and outdoor adventures, including hiking, picnicking, and wildlife viewing, making it a perfect escape into nature.
  2. United States Military Academy: Situated 11.3km away, this prestigious academy provides a glimpse into military life and history, with impressive architecture and rich traditions that showcase the training of future leaders.
  3. Van Cortlandt Manor: Also 11.3km from Peekskill, this historic house offers a cultural experience with its beautifully preserved grounds and exhibitions that highlight the region's colonial past.

Things to do recommended for couples

For a romantic getaway in Peekskill, consider a concert at Tarrytown Music Hall, a visit to Brotherhood Winery for a touch of romance, or enjoy a luxurious day at The Golf Club at Mansion Ridge. Each offers a unique experience for couples to cherish together.

Things to do recommended for families

Families visiting Peekskill can unwind at Peekskill Landing Park, perfect for relaxation. For sports enthusiasts, Michie Stadium offers thrilling games just 11.3km away. For an adrenaline rush, head to Grand Prix New York / Spins Bowl, 17.7km away, for karting adventures!

Things to do recommended for groups

Experience the charm of Peekskill with a shopping spree at Woodbury Common Premium Outlets, catch a show at the Paramount Hudson Valley Theater, or enjoy a round of golf at the Garrison Golf Club, all perfect for group outings!

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

When planning your trip—whether you're travelling with a group, family, pets, or seeking extended stays—be sure to filter your options according to your main priorities. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Peekskill with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor space for group activities. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Peekskill with young kids: Travelling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, keeping in mind your closeness to family-friendly attractions can enhance your travel experience.
  • Taking your pets with you to Peekskill: For many, a family vacation isn’t truly fulfilling without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Most 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 in search of vacation rentals with special offers for stays of a month or more, 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 consider adding amenities like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay in Peekskill

Peekskill, New York, offers a delightful blend of family-friendly vibes and outdoor adventures, making it an ideal vacation spot. Explore charming neighborhoods and nearby cities, each providing a unique atmosphere, from romantic strolls along the Hudson River to budget-friendly family excursions. With friendly locals and a welcoming community, your travel experience in and around Peekskill promises to be memorable and enriching.

  • Bear Mountain: Located a mere 8.0km from Peekskill, Bear Mountain is a haven for outdoor enthusiasts and families alike. This city is renowned for its stunning natural landscapes, including the expansive Bear Mountain State Park, where visitors can enjoy hiking, skiing, and breathtaking views of the surrounding mountains and lakes. The area is perfect for adventure seekers, providing access to ski resorts and outdoor activities year-round. Whether you're picnicking by the lake or exploring scenic trails, Bear Mountain promises a memorable experience immersed in nature.
  • Cortlandt: Just 3.2km away from Peekskill, Cortlandt offers a delightful blend of outdoor activities and family-friendly attractions. This charming city is known for its picturesque scenery and vibrant arts scene, featuring local education centres and a bustling shopping centre. Visitors can enjoy peaceful moments by the lake or explore historic sites within the area. With its engaging community atmosphere and proximity to the national state park, Cortlandt is an ideal spot for those seeking relaxation and exploration in a beautiful setting.
  • Buchanan: Also situated 3.2km from Peekskill, Buchanan is a quaint city that beckons outdoor lovers and families. With its serene landscapes, including nearby lakes and mountains, this destination is perfect for leisurely strolls and enjoying the outdoors. Visitors can engage in educational pursuits or unwind at local shopping areas and private country clubs. Buchanan's proximity to the national state park enhances its appeal, offering a blend of scenic beauty and recreational options for a fulfilling getaway.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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

Are you hoping to save on your next getaway? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect spot for your travels!

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a convenient way to plan your travel experiences. You can create new trips, pick up right where you left off, or easily view and organize your travel plans. Any properties you've saved or booked previously can now be accessed under Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/en-ca/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)
  • The Golf Club at Mansion Ridge (14 mi / 22.5 km)
  • Brotherhood Winery (16.3 mi / 26.2 km)
  • Patriot Hills Golf Club (7.2 mi / 11.7 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

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)
  • Lake Tiorati Beach (8.9 mi / 14.3 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 when booking a vacation rental?
When considering a vacation rental in Peekskill, New York, one of the most appealing areas to stay in is the waterfront district. This vibrant neighbourhood offers stunning views of the Hudson River and a delightful atmosphere, superb for leisurely strolls. You'll find a variety of properties available here, ranging from charming historic homes to modern apartments, suiting various preferences and budgets.

Staying near the waterfront also places you within easy reach of top attractions such as the Peekskill Riverfront Green Park, where you can enjoy outdoor activities, picnics, and seasonal events. Additionally, the nearby Paramount Hudson Valley Theatre often showcases live performances and cultural events, making it a fantastic spot for entertainment enthusiasts.

Another excellent area to consider is the historic downtown district. This area is filled with quaint shops, delightful cafes, and restaurants that reflect the local culture. The number of vacation rentals here is quite substantial, allowing you to choose a place that suits your style. While in downtown Peekskill, you can explore the Peekskill Museum, which offers insights into the city's rich history and art scene.
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 travelling 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.
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 options available throughout the area. These properties typically feature spacious interiors with multiple bedrooms, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups. Many of these vacation houses also offer outdoor spaces such as gardens or patios, great for relaxing after a day of exploring the nearby Hudson River waterfront and local parks.
Are there any family house rentals in Peekskill?
In Peekskill, New York, there are several family-friendly house rentals available, making it a great choice for those travelling with children. The neighbourhoods around the Hudson River offer spacious homes with amenities such as fully equipped kitchens, comfortable living areas, and often outdoor spaces for kids to enjoy.

Many of these properties are conveniently located near local parks, like Depew Park, which features playgrounds and picnic areas, superb for family outings. Additionally, the vibrant downtown area is just a short drive away, where visitors can explore charming shops, restaurants, and cultural attractions such as the Peekskill Museum.
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. 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, there are several pet-friendly house rentals available, making it a great choice for travellers with furry companions. Many of these vacation homes offer spacious living areas, modern kitchens, and outdoor spaces such as private gardens or patios where pets can enjoy the fresh air.
Are there any remote work vacation rentals in Peekskill?
In Peekskill, New York, there are several remote work-friendly vacation rentals available, making it an ideal choice for those looking to combine work and leisure. Many of these properties come equipped with essential amenities such as Wi-Fi, dedicated desks, and comfortable desk chairs, ensuring a productive working environment. 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 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 vacation rental?
The best time to visit Peekskill for a vacation rental is during the lively peak season from July to September. This summer stretch attracts visitors eager to enjoy the warm weather while exploring the charming riverside city. With temperatures typically ranging from the mid to high 20s Celsius, it's great for outdoor activities such as hiking in the nearby Hudson Highlands or taking leisurely strolls along the scenic waterfront.

July stands out as the most popular month, as it brings a vibrant atmosphere with various local events and festivals. This is a fantastic time for those looking to immerse themselves in Peekskill's rich culture, including its arts scene and dining options. The warm evenings are ideal for outdoor concerts and gatherings, making it a memorable experience for families and friends alike.

If you're considering a visit during a quieter time, October is a wonderful choice. The fall foliage in Peekskill is absolutely stunning, with the leaves turning vibrant shades of orange and red. This month offers a chance to appreciate the natural beauty without the summer crowds, while still enjoying mild temperatures that hover around the low to mid-teens Celsius, great for outdoor exploration and scenic drives along the Hudson River.
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.
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 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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

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