Holiday Rentals in Peekskill, NY

19 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Peekskill, NY holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

19 Holiday rentals and Airbnb in Peekskill, NY

Best family friendly Peekskill, NY holiday rentals

Among the 19 accommodations in Peekskill, NY, here are the 1 best family friendly rentals

Cozy Retreat W/ Pool, Cinema Room & Fire Pit - Peekskill, NY
9.6 15 reviews
Peekskill, NY
11/09 – 13/09
1273 €/nighttotal: 2546 € (2 )

Cozy Retreat W/ Pool, Cinema Room & Fire Pit

3 8
cottage , Lake Mohegan
This charming cottage is located just a short drive from the bustling town of Cold Spring, offering a peaceful retreat in the woods of Putnam Valley. The property has been highly rated by previous guests, receiving excellent reviews for its comfortable accommodation and tranquil setting.
The cottage offers three bedrooms and three bathrooms, comfortably sleeping up to eight guests. It is equipped with a range of amenities including a fully equipped kitchen, a swimming pool, a Jacuzzi, and a private deck with stunning views of the Hudson Valley.

Best Peekskill, NY holiday rentals with parking

Castle Retreat W/ Pool, Bbq, Game Room & Pets Ok! - Peekskill, NY
9.2 7 reviews
Peekskill, NY
11/09 – 13/09
1409 €/nighttotal: 2818 € (2 )

Castle Retreat W/ Pool, Bbq, Game Room & Pets Ok!

5 8
apartment , Ossining
This family-friendly holiday home in Ossining is situated a 15-minute walk from Sing Sing Correctional Facility and a 12-minute walk from Old Croton Aqueduct State Park.
Boasting 398 square meters of living space, this accommodation accommodates up to 13 guests with 5 bedrooms and 4 bathrooms, featuring a private swimming pool, garden, billiards, and free Wi-Fi, with on-site covered parking and proximity to outdoor activities.

Frequently asked questions about holiday rentals in Peekskill, NY

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

    The downtown area is a great option for a vacation rental. It's close to the riverfront, shops, restaurants, and the train station, making it easy to explore the city and surrounding areas.
  • What are the best Airbnb and holiday rentals in Peekskill, NY?

    The Peekskill Riverview House, Yellow House One Bedroom and Cozy 3 Bedroom House On Quiet Private Road are among the best Airbnb and holiday rentals in Peekskill, NY.

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

    The best time to book a vacation rental is during the shoulder seasons, from April to May and September to October. You'll avoid the crowds and enjoy pleasant weather.
  • 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 best budget-friendly activities in Peekskill, NY?

    You can enjoy a free walk along the Hudson Riverfront Green or explore the historic downtown area with its unique shops and art galleries. The Peekskill Farmers Market is also a great way to experience local produce without spending much.
  • What are the best holiday rentals with a pool in Peekskill, NY?

  • What are the best walking or cycling routes in Peekskill, NY?

    The Peekskill Riverfront Green offers a beautiful scenic walk or bike ride along the Hudson River. You can also explore the historic downtown area on foot, taking in the charming architecture and local shops.
  • What are the best rentals for families and kids in Peekskill, NY?

  • Are there pet-friendly attractions in Peekskill, NY?

    Yes, many places in Peekskill are pet-friendly! Charles Point Park is a great spot for a walk with your dog, and many restaurants have outdoor seating where you can enjoy a meal with your furry friend.
  • What are the best rentals or Airbnbs with a jacuzzi in Peekskill, NY?

  • What are the benefits of choosing a vacation rental in Peekskill, NY?

    Vacation rentals offer more space and privacy compared to a hotel. You can also enjoy the convenience of having a kitchen and laundry facilities, which can be especially helpful for families.
  • What are the top sports attractions and facilities in Peekskill, NY?

    Peekskill has a lot of sports facilities, including the Peekskill High School Stadium for high school football games and the Peekskill Riverfront Green for jogging and cycling. The city also has several parks with basketball courts and playgrounds.

Destinations nearby

Best Peekskill, NY holiday rentals with a balcony

Charming 2-bedroom Farmhouse With Ac In Putnam Valley - Peekskill, NY
Peekskill, NY
11/09 – 13/09
442 €/nighttotal: 884 € (2 )

Charming 2-bedroom Farmhouse With Ac In Putnam Valley

2 8
farm , Lake Mohegan
This rural property, a farm, is located in Putnam Valley, offering easy access to the United States Military Academy, which is 4.5 kilometres away, and Boscobel House and Gardens, 10.2 kilometres distant.
This farm provides accommodation for up to 8 guests with 2 bedrooms and 3 bathrooms, featuring air conditioning, an in-room kitchen, and on-site laundry facilities, with the added benefit of a garden and proximity to the Hudson Valley Center for Contemporary Art and Willow Ridge Farm for evening entertainment.

Best pet friendly Peekskill, NY holiday rentals

Among the 19 accommodations in Peekskill, NY, here are the 1 best pet friendly rentals

Welcome Spring Estate An Hr From Nyc - Peekskill, NY
10 108 reviews
Peekskill, NY
11/09 – 13/09
2922 €/nighttotal: 5844 € (2 )

Welcome Spring Estate An Hr From Nyc

1 8
house , Croton-on-Hudson
This eight-bedroom Croton-on-Hudson estate, approximately 16km from the Metro-North offering easy access to Midtown Manhattan, sits on 9 hectares of private land adjoining 80 hectares of protected nature trails near the Teatown Lake Reservation and the Old Croton Aqueduct Trail.
The farmhouse, built circa 1895, boasts a gourmet kitchen, piano, library, expansive dining room, tennis court, lake for kayaking, and accommodates up to 16 guests, with the option of adding a cottage; nearby attractions include Bald Mountain and West Point.
©2026 cozycozy.com