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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.

West Point Hudson Valley Getaway - Peekskill, NY
9.9 66 reviews
Peekskill, NY
06/20 – 06/27
$530/nighttotal: $3710 (7 )

West Point Hudson Valley Getaway

1 6
apartment , Highland Falls
This charming apartment is located in the Ondaora Park community in Highland Falls, just a short distance from Thayer Gates and West Point. It has received excellent ratings for its cleanliness, location, and overall experience.
The entire house is available for rent, accommodating up to six guests. The apartment offers a range of amenities including a swimming pool, garden, parking, and a fully equipped kitchen with a refrigerator and dishwasher.
Peekchill: Walk To Coffeehouse & Forest - Peekskill, NY
9.6 38 reviews
Peekskill, NY
06/20 – 06/27
$960/nighttotal: $6720 (7 )

Peekchill: Walk To Coffeehouse & Forest

1 6
apartment , Peekskill
This charming house is located on a quiet residential street in Peekskill, just a short walk from Depew Park, Blue Mountain Reservation, and the Metro North station. Guests consistently rate this property as excellent for cleanliness, location, and overall experience. This two-bedroom, two-bathroom home comfortably accommodates four guests. The fully equipped kitchen, spacious living areas, and private backyard with a fire pit provide everything you need for a relaxing and enjoyable stay.

Best Peekskill, NY vacation rentals with parking

Spectacular River& Mountain Views Near West Point! - Peekskill, NY
10 57 reviews
Peekskill, NY
06/20 – 06/27
$2167/nighttotal: $15169 (7 )

Spectacular River& Mountain Views Near West Point!

1 6
apartment , Fort Montgomery
This 3-bedroom apartment is located in Fort Montgomery, about an hour north of New York City, offering stunning views of the Hudson River and mountains. It has excellent user, location, and cleanliness ratings.
The apartment is spacious and modern, accommodating up to 8 guests. It features a private hiking trail, a private deck and backyard, and is close to West Point Academy, the Appalachian Trail, Bear Mountain, and Cold Springs, offering access to numerous outdoor activities.
Walk To Wp Gate + Free Parking! - Peekskill, NY
9.8 23 reviews
Peekskill, NY
06/20 – 06/27
$460/nighttotal: $3220 (7 )

Walk To Wp Gate + Free Parking!

2 6
apartment , Highland Falls
This Highland Falls apartment rental is conveniently located within a 10-minute walk of the United States Military Academy, the Hudson River, and the West Point Museum.
The two-bedroom, one-bathroom unit sleeps six, features a fully equipped kitchen with a dishwasher, in-unit laundry, free WiFi, on-site parking, and a terrace; nearby attractions include Christl Arena and Michie Stadium, both within 2 miles.
Walk To Wp Gate And Free Parking - Peekskill, NY
Peekskill, NY
06/20 – 06/27
$458/nighttotal: $3206 (7 )

Walk To Wp Gate And Free Parking

1 6
apartment , Highland Falls
This Highland Falls apartment rental is conveniently located near West Point's WP Gate, 10 miles from Bear Mountain State Park, and 15 miles from Metro-North's Harriman station.
The 1100-square-foot unit features one bedroom, one bathroom, a fully equipped kitchen with a fridge and microwave, in-unit laundry, free Wi-Fi, and parking; it comfortably sleeps up to 11 guests.
Secluded Getaway: Bear Mt, Cold Spring, Beacon, West Point! - Peekskill, NY
9.8 68 reviews
Peekskill, NY
06/20 – 06/27
$1195/nighttotal: $8365 (7 )

Secluded Getaway: Bear Mt, Cold Spring, Beacon, West Point!

3 6
apartment , Fort Montgomery
This apartment is located just one hour from New York City and 10 minutes from West Point, offering a peaceful retreat in the mountains. The property has earned excellent ratings for its location, cleanliness, and overall experience.
The apartment has three bedrooms and three bathrooms, providing ample space for families or groups. Guests can enjoy a heated pool, a hot tub, a terrace, a garden, a spa, and parking, all within a serene mountain setting.

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.

Secluded Getaway: Bear Mt, Cold Spring, Beacon, West Point! - Peekskill, NY
9.8 68 reviews
Peekskill, NY
06/20 – 06/27
$1195/nighttotal: $8365 (7 )

Secluded Getaway: Bear Mt, Cold Spring, Beacon, West Point!

3 6
apartment , Fort Montgomery
This apartment is located just one hour from New York City and 10 minutes from West Point, offering a peaceful retreat in the mountains. The property has earned excellent ratings for its location, cleanliness, and overall experience.
The apartment has three bedrooms and three bathrooms, providing ample space for families or groups. Guests can enjoy a heated pool, a hot tub, a terrace, a garden, a spa, and parking, all within a serene mountain setting.
Charming Hudson Valley 3-bedroom Family Getaway - Peekskill, NY
Peekskill, NY
06/20 – 06/27
$403/nighttotal: $2821 (7 )

Charming Hudson Valley 3-bedroom Family Getaway

1 6
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.

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.

Walk To Wp Gate + Free Parking! - Peekskill, NY
9.9 33 reviews
Peekskill, NY
06/20 – 06/27
$380/nighttotal: $2660 (7 )

Walk To Wp Gate + Free Parking!

2 6
apartment , Highland Falls
This Highland Falls apartment rental is centrally located, offering easy access to Hudson Valley attractions.
The two-bedroom unit, sleeping up to six guests, features a fully equipped kitchen, in-unit laundry, free high-speed Wi-Fi, and free on-site parking.
Long Dog Inn - Peekskill, NY
10 20 reviews
Peekskill, NY
06/20 – 06/27
$1755/nighttotal: $12285 (7 )

Long Dog Inn

1 6
apartment , Highland Falls
The Long Dog Inn is a pet-friendly Highland Falls house located a short walk from Thayer Gate, the main entrance to the United States Military Academy at West Point.
This four-bedroom, three-bathroom home sleeps twelve guests and features a fully stocked kitchen, Smart TVs, high-speed Wi-Fi, a laundry room, a game room with ping pong and chess, and a fenced backyard.
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