Holiday Rentals in Peekskill, NY

19 available vacation rental offers

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

Best Holiday rentals and Airbnb offers in Peekskill, NY

Best family friendly Peekskill, NY holiday rentals

Among the 19 accommodations in Peekskill, NY, here are the 4 best family friendly rentals

Chic Cozy Upstate Cabin Just 1 Hr From Nyc! - Peekskill, NY
9.9 81 reviews
Peekskill, NY
21/08 – 23/08
SG$1953/nighttotal: SG$3906 (2 )

Chic Cozy Upstate Cabin Just 1 Hr From Nyc!

4 7
apartment , Shrub Oak
This four-bedroom cabin is situated in Shrub Oak, just 80 kilometres north of New York City, offering easy access to the Metro North train line and the Hudson Valley's scenic beauty.
The property boasts a private and secluded location on 1 hectare of land, featuring multiple living spaces, a well-equipped kitchen, outdoor amenities, and a lower level apartment, ideal for families or groups of up to eight guests.
The Blue Lake House! - Peekskill, NY
9.4 61 reviews
Peekskill, NY
21/08 – 23/08
SG$1468/nighttotal: SG$2936 (2 )

The Blue Lake House!

1 7
apartment , Lake Mohegan
This apartment is situated in Lake Mohegan, just a short drive from a shopping centre and golf courses, offering a peaceful retreat with stunning lake views. It has received excellent ratings for user experience, location, and cleanliness.
The apartment can comfortably accommodate up to 10 guests and features a fully equipped kitchen, three bathrooms, and a garden. Guests can enjoy a range of amenities, including a Jacuzzi, kayaks, paddleboards, a fishing boat, and direct access to the lake for swimming and other water activities.
Hudson Valley Mountaintop Riverview - Peekskill, NY
9.9 177 reviews
Peekskill, NY
21/08 – 23/08
SG$1672/nighttotal: SG$3344 (2 )

Hudson Valley Mountaintop Riverview

4 7
apartment , Highland Falls
This Mediterranean-style house is located 80 kilometres north of Manhattan, close to the Appalachian Trail and the towns of West Point, Cold Spring, and Garrison. The property enjoys excellent ratings for location, cleanliness, and user experience.
The spacious apartment has three bedrooms and two bathrooms, comfortably accommodating up to eight guests. Guests can enjoy panoramic views of the Hudson River and Valley, a fully equipped kitchen, a garden, and parking, making it a perfect choice for families and groups seeking a relaxing getaway.
Modern, Magical Woodsy Escape 1 Hour From Nyc - Peekskill, NY
10 31 reviews
Peekskill, NY
21/08 – 23/08
SG$2013/nighttotal: SG$4026 (2 )

Modern, Magical Woodsy Escape 1 Hour From Nyc

4 7
apartment , Shrub Oak
The Lodge is located in Putnam Valley, just 80 kilometres north of New York City, offering a peaceful retreat in the Hudson Valley. It has received excellent user ratings and is a great choice for travellers seeking a comfortable and spacious home away from home.
The self-contained apartment spans 372 square metres and can accommodate up to eight guests, with four bedrooms and three bathrooms. It includes a fully equipped kitchen, a garden, parking, air conditioning, internet access, and a range of amenities for relaxation and entertainment, such as a fire pit, a private wooded area for hiking, and a "sunset ridge" for enjoying evening views.

Best Peekskill, NY holiday rentals with parking

Charming Hudson Valley 3-bedroom Family Getaway - Peekskill, NY
Peekskill, NY
11/09 – 13/09
SG$749/nighttotal: SG$1498 (2 )

Charming Hudson Valley 3-bedroom Family Getaway

1 8
house , Stony Point
This Stony Point house, located in Tomkins Cove, is 16km from Bear Mountain State Park and 21km from The Palisades Center mall, offering easy access to both attractions.
The 121-square-metre property boasts one bedroom, one bathroom, sleeps fifteen guests, and includes a fully equipped kitchen, private terrace, free Wi-Fi, and free parking.
Castle Retreat W/ Pool, Bbq, Game Room & Pets Ok! - Peekskill, NY
9.2 7 reviews
Peekskill, NY
11/09 – 13/09
SG$2094/nighttotal: SG$4188 (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

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

    You definitely don't want to miss the historic Hudson River Museum. It's a great place to learn about the region's history and art. And for a beautiful view, take a stroll along the Peekskill waterfront. You'll see the iconic Peekskill lighthouse and enjoy the stunning Hudson River scenery.
  • 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. You'll be close to the shops, restaurants, and attractions. The historic district offers a charming atmosphere with beautiful Victorian architecture. You'll find plenty of options for a comfortable stay.
  • 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?

    The Hudson River Museum has interactive exhibits that are perfect for kids. The Peekskill Riverfront Green is a great place to have a picnic or play games. For a fun day out, visit the Peekskill Farmers Market. It's a great place to find fresh produce and local crafts.
  • What 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 during the shoulder season, from April to May or September to October. You'll avoid the crowds and get better deals on accommodation. The weather is still pleasant during these months, perfect for exploring the area.
  • 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?

    The Peekskill Jazz Festival in June is a popular event, featuring live music and food stalls. The Peekskill Fall Festival in October is another great option, with a parade, craft fair, and pumpkin carving contest.
  • What are the best rentals or Airbnbs with a jacuzzi in Peekskill, NY?

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

    A walk along the Peekskill Riverfront Green is a great way to spend a sunny afternoon. The Peekskill Farmers Market is also a great option for a budget-friendly day out. You can find local produce, crafts, and even live music.
  • What are the best restaurants with local dishes in Peekskill, NY?

    The Peekskill Brewery is a popular spot for local craft beers and pub grub. For a more upscale experience, try The Restaurant at the Peekskill Hotel. They serve delicious seasonal dishes with fresh local ingredients.
  • What are the best walking or cycling routes in Peekskill, NY?

    The Peekskill Riverfront Green Trail is a great option for a leisurely walk or bike ride. It follows the Hudson River and offers stunning views of the water and the surrounding hills. For a more challenging ride, try the Peekskill to Croton-on-Hudson Bike Path.
  • Are there pet-friendly attractions in Peekskill, NY?

    The Peekskill Riverfront Green is a great place to take your dog for a walk or a run. Many restaurants and cafes in the downtown area also welcome well-behaved dogs on their patios.
  • What are the benefits of choosing a vacation rental in Peekskill, NY?

    Vacation rentals offer more space and privacy than hotels. They often come with kitchens, so you can save money by preparing some of your meals. You also have the flexibility to come and go as you please.
  • What are the top sports attractions and facilities in Peekskill, NY?

    The Peekskill High School has a great sports complex with facilities for baseball, soccer, and track and field. The Peekskill Riverfront Green is also a popular spot for outdoor sports like running, cycling, and kayaking.

Destinations nearby

Best Peekskill, NY holiday rentals with a balcony

Storm King Lodge - Storm King Art Center, West Point, Woodbury Commons Outlets - Peekskill, NY
9.6 5 reviews
Peekskill, NY
11/09 – 13/09
SG$1872/nighttotal: SG$3744 (2 )

Storm King Lodge - Storm King Art Center, West Point, Woodbury Commons Outlets

4 8
chalet , Firthcliffe
Storm King Lodge, a country house, is located in Mountainville, New York, within the Lower Hudson River Valley, approximately 97 kilometres from NYC and close to Storm King Art Centre and West Point.
This 279 square metre lodge offers 4 bedrooms and 4 bathrooms, accommodating up to 8 guests with its own kitchen, air conditioning, terrace, garden, and access to nearby hiking and cultural attractions.
Charming 2-bedroom Farmhouse With Ac In Putnam Valley - Peekskill, NY
Peekskill, NY
11/09 – 13/09
SG$657/nighttotal: SG$1314 (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 2 best pet friendly rentals

Hudson Valley Retreat/pool/spa/firepit/pickleball - Peekskill, NY
9.8 154 reviews
Peekskill, NY
21/08 – 23/08
SG$2962/nighttotal: SG$5924 (2 )

Hudson Valley Retreat/pool/spa/firepit/pickleball

1 7
apartment , Woodbury
This spacious six-bedroom home is situated in a peaceful rural area of Woodbury, just 10 kilometres from the Woodbury Common Premium Outlets and 10 kilometres from West Point. The property has received excellent ratings for location, cleanliness, and user experience.
The accommodation is ideal for large families or groups, sleeping up to 16 guests. The property offers a range of amenities, including a private pool, hot tub, outdoor fireplace, a fully equipped kitchen, and a games court, ensuring there is something for everyone to enjoy.
Magic On This Mountain! - Peekskill, NY
Peekskill, NY
21/08 – 23/08
SG$3263/nighttotal: SG$6526 (2 )

Magic On This Mountain!

1 7
apartment , Stony Point
This property is situated in the mountains near Stony Point, a 72km drive from New York City and close to Woodbury Commons, offering a peaceful retreat with stunning views. The house has three bedrooms and two bathrooms, comfortably accommodating up to 16 guests. The property boasts a spacious outdoor area with a fire ring, two streams, and a relaxing deck, perfect for enjoying the mountain views and exploring the nearby hiking trails.
©2026 cozycozy.com