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

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.

Cozy Retreat W/ Pool, Cinema Room & Fire Pit - Peekskill, NY
9.9 122 reviews
Peekskill, NY
09/11 – 09/13
$1447/nighttotal: $2894 (2 )

Cozy Retreat W/ Pool, Cinema Room & Fire Pit

1 8
apartment , Lake Mohegan
This charming cottage is located in Putnam Valley, just a short drive from Cold Spring and the Hudson River, offering a peaceful retreat in a wooded setting. The cottage consistently receives excellent ratings for its cleanliness, location, and overall experience.
The cozy cabin features three bedrooms and three bathrooms, comfortably accommodating up to eight guests. Enjoy modern amenities like a fully equipped kitchen, air conditioning, a private pool, and a spacious deck with breathtaking sunset views over the Hudson Valley.
Bear Mountain House. - Peekskill, NY
10 15 reviews
Peekskill, NY
09/11 – 09/13
$941/nighttotal: $1882 (2 )

Bear Mountain House.

3 8
apartment , Fort Montgomery
This Garrison cottage is located in Philipstown, just a short drive from the Bear Mountain Bridge, 15 minutes from West Point, and 60 minutes from NYC. This property has excellent user ratings and is a great choice for families and groups. The home has 3 bedrooms and 3 bathrooms, comfortably accommodating up to 8 guests. Enjoy amenities such as a fully equipped kitchen, a private terrace, and a garden, perfect for relaxing after a day of hiking or exploring the nearby attractions.

Best Peekskill, NY vacation rentals with parking

Cozy Retreat W/ Pool, Cinema Room & Fire Pit - Peekskill, NY
9.6 15 reviews
Peekskill, NY
09/11 – 09/13
$1472/nighttotal: $2944 (2 )

Cozy Retreat W/ Pool, Cinema Room & Fire Pit

3 8
cottage , Lake Mohegan
This charming cottage is located in Lake Peekskill, just a short drive from Cold Spring and close to attractions like Manitoga and Boscobel House and Gardens. Guests consistently rate this property excellent for its peaceful, wooded setting and stunning views of the Hudson Valley.
The cottage has three bedrooms and three bathrooms, comfortably accommodating up to eight guests. Enjoy modern amenities like air conditioning, a private deck, a swimming pool, a jacuzzi, and a fully equipped kitchen, all while being surrounded by the natural beauty of the Hudson Valley.
Green Country House Garrison - Peekskill, NY
9.9 33 reviews
Peekskill, NY
09/11 – 09/13
$610/nighttotal: $1220 (2 )

Green Country House Garrison

1 8
apartment , Highland Falls
This Peekskill apartment is located in a quiet area, just a short drive from the city's downtown and the Hudson River waterfront. The apartment has received excellent ratings for its location, cleanliness, and user experience.
The three-bedroom, three-bathroom rental comfortably sleeps eight guests. The apartment includes a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, as well as air conditioning, a garden, a fitness center, parking, and a fireplace.
Castle Retreat W/ Pool, Bbq, Game Room & Pets Ok! - Peekskill, NY
9.2 7 reviews
Peekskill, NY
09/11 – 09/13
$1629/nighttotal: $3258 (2 )

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

5 8
apartment , Ossining
This family-friendly vacation home in Ossining is located a 15-minute walk from Sing Sing Correctional Facility and a 12-minute walk from Old Croton Aqueduct State Park.
This spacious 4280 square foot residence offers 5 bedrooms, 4.5 bathrooms, accommodates up to 13 guests, and features a private swimming pool, garden, and covered on-site parking.
Charming Hudson Valley 3-bedroom Family Getaway - Peekskill, NY
Peekskill, NY
09/11 – 09/13
$582/nighttotal: $1164 (2 )

Charming Hudson Valley 3-bedroom Family Getaway

1 8
house , Stony Point
This Stony Point house rental, located in Tomkins Cove, offers easy access to Bear Mountain State Park (10 miles) and Palisades Center mall (13 miles).
The 1300-square-foot home features one bedroom, one bathroom, and can comfortably accommodate up to 15 guests, boasting a fully equipped kitchen, free Wi-Fi, private parking, and a terrace.

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.

Destinations nearby

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.

Charming 2-bedroom Farmhouse With Ac In Putnam Valley - Peekskill, NY
Peekskill, NY
09/11 – 09/13
$511/nighttotal: $1022 (2 )

Charming 2-bedroom Farmhouse With Ac In Putnam Valley

2 8
farm , 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.

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.

Welcome Spring Estate An Hr From Nyc - Peekskill, NY
10 108 reviews
Peekskill, NY
09/11 – 09/13
$3378/nighttotal: $6756 (2 )

Welcome Spring Estate An Hr From Nyc

1 8
house , Croton-on-Hudson
This 8-bedroom estate is located in Croton-on-Hudson, about an hour from New York City, and is surrounded by 200 acres of protected land. The property has received excellent ratings for location, cleanliness, and user experience. This spacious home features 8 bedrooms, 7 bathrooms, and can comfortably accommodate up to 16 guests. The farmhouse offers a gourmet kitchen, a fire pit, a tennis court, hiking trails, and access to a lake for kayaking.
Castle Retreat W/ Pool, Bbq, Game Room & Pets Ok! - Peekskill, NY
9.2 7 reviews
Peekskill, NY
09/11 – 09/13
$1629/nighttotal: $3258 (2 )

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

5 8
apartment , Ossining
This family-friendly vacation home in Ossining is located a 15-minute walk from Sing Sing Correctional Facility and a 12-minute walk from Old Croton Aqueduct State Park.
This spacious 4280 square foot residence offers 5 bedrooms, 4.5 bathrooms, accommodates up to 13 guests, and features a private swimming pool, garden, and covered on-site parking.
Cozy Retreat W/ Pool, Cinema Room & Fire Pit - Peekskill, NY
9.6 15 reviews
Peekskill, NY
09/11 – 09/13
$1472/nighttotal: $2944 (2 )

Cozy Retreat W/ Pool, Cinema Room & Fire Pit

3 8
cottage , Lake Mohegan
This charming cottage is located in Lake Peekskill, just a short drive from Cold Spring and close to attractions like Manitoga and Boscobel House and Gardens. Guests consistently rate this property excellent for its peaceful, wooded setting and stunning views of the Hudson Valley.
The cottage has three bedrooms and three bathrooms, comfortably accommodating up to eight guests. Enjoy modern amenities like air conditioning, a private deck, a swimming pool, a jacuzzi, and a fully equipped kitchen, all while being surrounded by the natural beauty of the Hudson Valley.
Cozy Retreat W/ Pool, Cinema Room & Fire Pit - Peekskill, NY
9.9 122 reviews
Peekskill, NY
09/11 – 09/13
$1447/nighttotal: $2894 (2 )

Cozy Retreat W/ Pool, Cinema Room & Fire Pit

1 8
apartment , Lake Mohegan
This charming cottage is located in Putnam Valley, just a short drive from Cold Spring and the Hudson River, offering a peaceful retreat in a wooded setting. The cottage consistently receives excellent ratings for its cleanliness, location, and overall experience.
The cozy cabin features three bedrooms and three bathrooms, comfortably accommodating up to eight guests. Enjoy modern amenities like a fully equipped kitchen, air conditioning, a private pool, and a spacious deck with breathtaking sunset views over the Hudson Valley.
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