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Peekskill, NY vacation rentals
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Best Vacation rentals and Airbnb offers in Peekskill, NY

Discover Central Vacation Rentals in Peekskill, NY

Stay in downtown Peekskill, NY to keep top attractions within walking distance. Browse our central vacation rentals and find your perfect base.

Peekskill Apartment In The Center Of Downtown - Peekskill, NY
9.7 19 reviews

Peekskill Apartment In The Center Of Downtown

apartment, Peekskill
This 2-bedroom, 2-bathroom dwelling offers a prime downtown Peekskill location, placing you steps from restaurants and live music venues.
This residence accommodates up to 4 guests, featuring a kitchen equipped with a fridge and microwave, plus air conditioning and internet access.
Charming Home In Peekskill Ny - Peekskill, NY
9.9 122 reviews

Charming Home In Peekskill Ny

apartment, Peekskill
This two-bedroom apartment is located in a quiet cul-de-sac in Peekskill, a short two-minute drive from the Hudson Valley Presbyterian Hospital and less than 10 minutes from downtown Peekskill with its restaurants and attractions. The apartment offers a full first floor with a living room, kitchen, and a private backyard, ideal for families or groups of up to six people.
Charming Riverview House At The Inn On The Hudson - Peekskill, NY
9.3 83 reviews

Charming Riverview House At The Inn On The Hudson

apartment, Peekskill
This beautiful apartment is located on the grounds of the Inn on the Hudson in Peekskill, offering stunning views of the Hudson River and is just a short walk from the Peekskill waterfront. This property has been rated excellent for location, cleanliness and user experience.
This spacious 3-bedroom, 3-bathroom home can comfortably accommodate up to 8 guests. Enjoy access to a fully equipped kitchen, outdoor living spaces, a seasonal pool, and a 24/7 coffee and tea area.
The Hudson Hideaway - Peekskill, NY
10 2 reviews

The Hudson Hideaway

apartment, Peekskill
This 2-bedroom, 1-bathroom apartment is located in a quiet Peekskill neighborhood, offering easy access to the Lower Hudson Valley and is an hour's commute from New York City via Metro-North.
This pet-friendly unit accommodates up to 6 guests and features air conditioning, internet, and a kitchen, serving as a convenient base for exploring nearby Slainte restaurant and the Hudson Valley Theater.

Best Peekskill, NY vacation rentals with air conditioning

Luxury Lake House Sauna 1h From Nyc - Peekskill, NY
10 182 reviews

Luxury Lake House Sauna 1h From Nyc

apartment, Lake Mohegan
This Lake Mohegan lakefront apartment rental boasts a private dock, large deck, and backyard, located 20 minutes from West Point and Bear Mountain, and an hour from New York City.
The 4-guest unit features a heated bathroom floor, an 86-inch TV, a full kitchen with lake views, free Tesla charging (adapter included for other EVs), and excellent guest reviews for cleanliness and location.
Serene Mountain Top Views Overlooking Hudson River And Surrounding Highlands - Peekskill, NY
9.8 141 reviews

Serene Mountain Top Views Overlooking Hudson River And Surrounding Highlands

cottage, Fort Montgomery
This charming cottage is located in Fort Montgomery, just minutes from West Point Academy, Bear Mountain State Park, and Woodbury Common Premium Outlets, offering easy access to attractions and the beauty of the Hudson Valley. The cottage boasts excellent user ratings, reflecting its comfortable and convenient accommodations.
The cottage is a cozy 650 square foot space with one bedroom, one bathroom, and a capacity of four guests. Guests can enjoy a fully equipped kitchen, central air, cable TV, a private patio, and a Tesla destination charger, making it an ideal choice for a relaxing and enjoyable stay.
Lake Retreat Farm Style W Kayak Bbq Patio Fire Pit - Peekskill, NY
10 7 reviews

Lake Retreat Farm Style W Kayak Bbq Patio Fire Pit

apartment, Lake Mohegan
This one-bedroom lake house near Lake Mohegan offers direct lake access and is conveniently located within a short distance of local restaurants, hiking trails, and attractions. The pet-friendly rental accommodates up to three guests and features a spacious yard with patio furniture, a BBQ grill, a fire pit, and an equipped kitchen for a nature-focused getaway.
Charming Studio Apartment - Peekskill, NY
9.9 55 reviews

Charming Studio Apartment

apartment, Peekskill
This Cortlandt Manor studio, a short 5-10 minute drive from Peekskill's downtown area, offers easy access to the Hudson Valley MOCA, Paramount Hudson Valley Theater, and NY Presbyterian Hudson Valley Hospital.
The unit features a queen-size bed, a fully equipped kitchen with a Keurig coffee maker, a washer/dryer, a large deck with BBQ, and keyless entry; it comfortably accommodates two guests and is near Annsville Creek Preserve and Blue Mountain Reservation hiking trails.

Frequently Asked Questions about vacation rentals in Peekskill, NY

  • What should a first-time visitor not miss in Peekskill, NY?

    Peekskill has a lot to offer, but you shouldn't miss the historic Hudson River Museum. It's a great place to learn about the city's history and art. And of course, you have to take a stroll along the beautiful waterfront, especially during sunset.
  • What are the best Airbnb and vacation rentals in Peekskill, NY?

    The Peekskill Riverview House, Yellow House One Bedroom and Cozy 3 Bedroom House On Quiet Private Road are the most popular Airbnb and vacation rentals in Peekskill, NY among travelers.

  • Which neighborhood in Peekskill, NY should you consider for a vacation rental?

    The downtown area is a great choice for a vacation rental, especially if you want to be close to the action. You'll be within walking distance of shops, restaurants, and the waterfront. The residential neighborhood of Cortlandt, just north of downtown, is also a good option if you prefer a quieter atmosphere.
  • What are the most popular Airbnbs in Peekskill, NY?

    Among the Airbnbs in Peekskill, NY, The Peekskill Riverview House, Yellow House One Bedroom and Hudson Valley House are the most popular ones.

  • What are the top family-friendly attractions in Peekskill, NY?

    Peekskill is a great place for families. The Hudson River Museum has a children's area, and the Charles Point Park is a popular spot for picnics and playing. The Peekskill Farmers Market is also a fun experience, especially for kids who love to explore different foods.
  • What are the best vacation rentals with a pool in Peekskill, NY?

    Rainbow Rest - Pristine Apt In A Tranquil Setting, The Lake House and The Cottage At Oasis Cove are the best vacation rentals with a pool in Peekskill, NY.

  • When is the best time to book a vacation rental in Peekskill, NY?

    The best time to book a vacation rental in Peekskill is in the spring or fall. The weather is pleasant and there are fewer crowds than during the peak summer season. However, if you're looking for a more festive atmosphere, the holiday season is also a great time to visit.
  • What are the best rentals for families and kids in Peekskill, NY?

  • What events or festivals should visitors check out in and around Peekskill, NY?

    Peekskill has a lot of events throughout the year. The Hudson River Valley Wine and Food Festival is a popular event, and the Peekskill Jazz Festival brings in a lot of music lovers. The city also has a great farmers market on Saturdays in the summer.
  • What are the best rentals or Airbnbs with a jacuzzi in Peekskill, NY?

  • What are the best budget-friendly activities in Peekskill, NY?

    You can easily enjoy Peekskill on a budget. Take a walk along the Hudson River, visit the historic downtown area, or check out the free events at the Hudson River Museum. The local parks are also great places to relax and enjoy the outdoors.
  • What are the best restaurants with local dishes in Peekskill, NY?

    Peekskill has a lot of great restaurants, but some of the local favorites include The Peekskill Brewery for their locally brewed beers and pub fare, and The Blue Pig for their farm-to-table dishes. Don't forget to try the local Hudson Valley apple cider donuts!
  • What are the best walking or cycling routes in Peekskill, NY?

    The Hudson River Greenway is a great option for both walking and cycling. It runs along the waterfront and offers beautiful views of the river. You can also take a walk or bike ride through the historic downtown area or explore the trails in the nearby parks.
  • Are there pet-friendly attractions in Peekskill, NY?

    Peekskill is a very dog-friendly city. Many of the parks and restaurants welcome pets, and there are even dog-friendly events throughout the year. The Hudson River Greenway is a great place to take your dog for a walk.
  • What are the benefits of choosing a vacation rental in Peekskill, NY?

    Vacation rentals offer more space and privacy than a hotel room, and they often come with amenities like a kitchen and laundry facilities. This can be especially helpful for families or groups traveling together. You can also enjoy the local neighborhood and feel more like a local when staying in a vacation rental.
  • What are the top sports attractions and facilities in Peekskill, NY?

    Peekskill has a few sports facilities, including the Peekskill High School Stadium for football and track and field, and the Peekskill Golf Course. You can also find a few local gyms and fitness centers in the area.

Popular destinations

Guest-Favorite Vacation Rentals with a Terrace in Peekskill, NY

Elevate your stay in Peekskill, NY with a vacation rental featuring a private balcony and stunning city skyline views.

Comfortable 2bd - Convenience & Style - 45min To Nyc - Great Food - Peekskill, NY
9.8 93 reviews

Comfortable 2bd - Convenience & Style - 45min To Nyc - Great Food

apartment, Croton-on-Hudson
This family-friendly apartment is located in Croton-on-Hudson, within easy reach of several popular parks and historical landmarks. It has received excellent user ratings, making it a popular choice for travelers.
The 800 square foot apartment has two bedrooms and can accommodate up to four guests. It features a fully equipped kitchen, a comfortable living area, a terrace or balcony, a garden, and parking, making it an ideal choice for families or groups of friends.
Charming 2-bedroom Farmhouse With Ac In Putnam Valley - Peekskill, NY
8.0 1 review

Charming 2-bedroom Farmhouse With Ac In Putnam Valley

manor house, Lake Mohegan
This Putnam Valley farm stay is located near the United States Military Academy and Boscobel House and Gardens, offering convenient access to cultural and historical sites.
This non-smoking gîte rural accommodates up to 8 guests with 2 bedrooms and 3 bathrooms, featuring air conditioning, internet, a kitchen, a terrace/balcony, and a garden.
Cherry Blossom Lake House - Peekskill, NY
10 1 review

Cherry Blossom Lake House

house, Lake Mohegan
Cherry Blossom Lake House, a vacation home in Lake Peekskill, is located 14 miles from Bear Mountain State Park and 21 miles from Metro-North Harriman Station.
This 240 square foot house offers 3 bedrooms, 2 bathrooms, and accommodates up to 11 guests with amenities including a full kitchen, air conditioning, jacuzzi, sauna, terrace, and parking.
Updated Home W/ Patio Half Mile To West Point - Peekskill, NY
9.8 71 reviews

Updated Home W/ Patio Half Mile To West Point

house, Highland Falls
This family-friendly vacation home in Highland Falls is conveniently located near United States Military Academy (USMA), West Point Museum, and Hudson River, offering easy access to iconic landmarks. With excellent ratings for location, cleanliness, and user experience, this house provides a comfortable and enjoyable stay for families or groups.
The house features three bedrooms, two bathrooms, and a floor area of 1100 square feet, comfortably accommodating up to six guests. It boasts a fully equipped kitchen with modern appliances, a private patio for outdoor relaxation, and amenities such as air conditioning, internet access, and parking.

Choose the Right Family-Friendly Vacation Rentals in Peekskill, NY

Booking a family-oriented vacation rental in Peekskill, NY keeps you close to top city attractions for a stress-free getaway.

'The Glabin’: Garrison Gem W/ Hot Tub & Fire Pit - Peekskill, NY
No reviews

'The Glabin’: Garrison Gem W/ Hot Tub & Fire Pit

house, Peekskill
House. Your accommodation will be located in Peekskill.
Facilities and services include a barbecue, air conditioning and a fridge. This is a family-friendly house!
'Croton Quarters' - Comfortable Apt With Modern Amenities Near Food, Nyc Close! - Peekskill, NY
10 7 reviews

'Croton Quarters' - Comfortable Apt With Modern Amenities Near Food, Nyc Close!

apartment, Croton-on-Hudson
This Croton-on-Hudson apartment rental is conveniently located near the river, a 3-minute drive from Van Cortlandt Manor and a 5-minute drive from Croton Point Park.
The two-bedroom, one-bathroom apartment sleeps four, features a fully equipped kitchen, in-unit laundry, free Wi-Fi, and a private garden with parking; enjoy nearby water activities and Hudson Valley exploration.
Croton Quarters-modern Amenities - Peekskill, NY
10 46 reviews

Croton Quarters-modern Amenities

apartment, Croton-on-Hudson
This Croton-on-Hudson apartment rental, located on the first floor of a historically significant former farmhouse and convenience store, is 1.9 miles from the train station and a 7-minute walk from restaurants.
The two-bedroom, one-bathroom unit sleeps four, features a chef's kitchen with high-end appliances, a private yard, free parking, an Xbox Series X, and is conveniently located near hiking trails and a 45-minute train ride from Grand Central Terminal.
Arkadia House
Mid-century Retreat With Pool & View - Peekskill, NY
9.9 46 reviews

Arkadia House Mid-century Retreat With Pool & View

apartment, Highland Falls
This Highland Falls rental is minutes from Cold Spring, West Point, and Beacon, offering easy access to Bear Mountain State Park and the Dia:Beacon art gallery.
The three-bedroom, two-bathroom apartment sleeps six, features a private pool overlooking the Hudson River, and includes a fully equipped kitchen with a fridge and dishwasher, plus air conditioning, internet, and parking.

Best Peekskill, NY vacation rentals with parking

Fabulous 3bdrm Home W/parking! - Peekskill, NY
9.4 11 reviews

Fabulous 3bdrm Home W/parking!

apartment, Highland Falls
Walk To Wp Gate + Free Parking! - Peekskill, NY
9.8 24 reviews

Walk To Wp Gate + Free Parking!

apartment, Highland Falls
Charming Highland Falls Home < 2 Mi To West Point! - Peekskill, NY
9.5 2 reviews

Charming Highland Falls Home < 2 Mi To West Point!

house, Highland Falls
Contemporary Cozy Cottage - Peekskill, NY
9.8 52 reviews

Contemporary Cozy Cottage

apartment, Lake Mohegan

Our Favorite 5-Star Vacation Rentals in Peekskill, NY

Elevate your stay in a luxury vacation rental or Airbnb in Peekskill, NY, featuring high-end finishes and a prime location.

Charming 2 Bedroom Cottage W/ Patio & Yard. - Peekskill, NY
9.7 130 reviews

Charming 2 Bedroom Cottage W/ Patio & Yard.

house, Peekskill

Top-Rated Pet-Friendly Vacation Rentals in Peekskill, NY

Discover pet-friendly vacation rentals in Peekskill, NY that prioritize comfort for both you and your dog.

Crystal Wave Lakehouse - Peekskill, NY
9.8 137 reviews

Crystal Wave Lakehouse

apartment, Lake Mohegan
Discover Natures Glory!  Perfect Family Home - Peekskill, NY
9.8 131 reviews

Discover Natures Glory! Perfect Family Home

apartment, Fort Montgomery
Modern, Sun-filled Farmhouse Retreat - Peekskill, NY
10 27 reviews

Modern, Sun-filled Farmhouse Retreat

apartment, Highland Falls
Crystal Cottage Retreat - Peekskill, NY
9.7 69 reviews

Crystal Cottage Retreat

apartment, Highland Falls

Search Vacation Rentals with Swimming Pool in Peekskill, NY

A Peekskill, NY vacation rental with a pool ensures a refreshing swim in the heart of the city is always an option.

Cozy Retreat W/ Pool, Cinema Room & Fire Pit - Peekskill, NY
9.6 16 reviews

Cozy Retreat W/ Pool, Cinema Room & Fire Pit

cottage, Lake Mohegan
The Cottage At Oasis Cove - Peekskill, NY
9.8 35 reviews

The Cottage At Oasis Cove

house, Verplanck
The Abbey Inn & Spa - Peekskill, NY
No reviews

The Abbey Inn & Spa

resort, Peekskill
3br Hudson River House Near Bear Mountain - Peekskill, NY
10 18 reviews

3br Hudson River House Near Bear Mountain

apartment, Highland Falls

Explore Vacation Rentals with Jacuzzi in Peekskill, NY

Unwind at the end of a busy city day with a private hot tub at these hand-selected vacation rentals in Peekskill, NY.

Croton Calm Retreat W/ Hot Tub - Peekskill, NY
9.7 44 reviews

Croton Calm Retreat W/ Hot Tub

apartment, Croton-on-Hudson
Hudson Valley Retreat W/hot Tub 15 Mins West Point - Peekskill, NY
9.9 44 reviews

Hudson Valley Retreat W/hot Tub 15 Mins West Point

apartment, Peekskill
'The Glabin’: Garrison Gem W/ Hot Tub & Fire Pit - Peekskill, NY
9.8 63 reviews

'The Glabin’: Garrison Gem W/ Hot Tub & Fire Pit

house, Peekskill
Cozy West Point Hide Away And Cadets Get Away - Peekskill, NY
9.9 124 reviews

Cozy West Point Hide Away And Cadets Get Away

resort, Highland Falls
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