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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 Carriage House Downtown Studio - Peekskill, NY
10 21 reviews

Peekskill Carriage House Downtown Studio

studio, Peekskill
This studio apartment is conveniently located just a short walk from downtown Peekskill, putting you within easy reach of restaurants, shops, and the historic Paramount Theater. Guests consistently rate this charming studio as excellent, making it a popular choice for travelers exploring the area.
The studio features a comfortable queen bed and a couch, making it perfect for couples or solo travelers. Guests can enjoy a kitchenette, air conditioning, free parking, and internet access, allowing them to relax and enjoy their stay.
The Peekskill Riverview House - Peekskill, NY
9.8 221 reviews

The Peekskill Riverview House

apartment, Peekskill
This Peekskill apartment is a fully renovated designer house overlooking the historic Peekskill Bay, just a 5-minute walk from the train station and downtown. The apartment boasts excellent user, location, and cleanliness ratings, making it a great choice for travelers. The apartment comfortably sleeps 6 guests in 3 bedrooms with 3 bathrooms. It features expansive decks offering breathtaking Hudson River views, a fully equipped kitchen, smart TVs, and easy access to restaurants, shops, and attractions.
Charming Riverview House At The Inn On The Hudson - Peekskill, NY
9.3 82 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.
Peekskill Carriage House Downtown Studio - Peekskill, NY
9.9 323 reviews

Peekskill Carriage House Downtown Studio

house, Peekskill
This Peekskill studio apartment is located in downtown Peekskill, within walking distance of restaurants, coffee shops, and the Paramount Theatre.
The 400-square-foot unit features a queen bed, couch, equipped kitchenette, and accommodates two guests; nearby hiking trails and the Hudson Valley are a short drive away.

Best Peekskill, NY vacation rentals with air conditioning

Home: 2 Mi To Thayer Gate At U.s. Military Academy - Peekskill, NY
10 7 reviews

Home: 2 Mi To Thayer Gate At U.s. Military Academy

apartment, Highland Falls
This Highland Falls vacation rental is conveniently located near Bear Mountain State Park, offering easy access to local attractions such as Manitoga/The Russel Wright Design Center and Woodbury Common Premium Outlets.
This 1,820-square-foot home features four bedrooms, three bathrooms, and accommodates eight guests, boasting a fully equipped kitchen, private patio, on-site laundry, and air conditioning.
Walk To Wp Gate + Free Parking! - Peekskill, NY
9.8 24 reviews

Walk To Wp Gate + Free Parking!

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.
Stylish Affordable 2br Steps From Thayer Gate+prkg - Peekskill, NY
9.7 321 reviews

Stylish Affordable 2br Steps From Thayer Gate+prkg

apartment, Highland Falls
This Highland Falls apartment is located just a 10-minute walk from the United States Military Academy, the Hudson River, and the West Point Museum, offering easy access to the area's historic attractions. Guests consistently rate the apartment excellent for location, cleanliness, and overall experience.
The two-bedroom apartment spans 1190 square feet and comfortably accommodates up to six guests. It offers modern amenities like a fully equipped kitchen, air conditioning, a garden, and parking, making it perfect for a comfortable and convenient stay.
*Forest Retreat* Rustic Luxury Near Bear Mt Hiking - Peekskill, NY
9.8 68 reviews

*Forest Retreat* Rustic Luxury Near Bear Mt Hiking

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.

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.

Bear Mountain House. - Peekskill, NY
10 16 reviews

Bear Mountain House.

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.
Room For Everyone: Spacious 6br West Point Retreat - Peekskill, NY
10 1 review

Room For Everyone: Spacious 6br West Point Retreat

apartment, Highland Falls
This Highland Falls rental is centrally located, minutes from West Point and Bear Mountain State Park.
This seven-bedroom, four-bathroom apartment boasts 1990 square feet of space, sleeps up to 15 guests, and includes two kitchens, two living rooms with 65" HDTVs, a deck with a fire pit and Blackstone griddle, four to five parking spaces, and high-speed Wi-Fi.
Croton Quarters - Comfortable Apartments, Nyc Close - Peekskill, NY
10 20 reviews

Croton Quarters - Comfortable Apartments, Nyc Close

apartment, Croton-on-Hudson
Croton Quarters apartments in Croton-on-Hudson, New York offer convenient access to Palisades Center mall (18 miles), Manhattanville College (19 miles), and Westchester County Airport (17 miles).
This two-bedroom, one-bathroom rental sleeps seven guests and features a fully equipped kitchen, private terrace with garden views, free Wi-Fi, free parking, and air conditioning; outdoor play equipment is available for families.
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.

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.

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.
Charming Highland Falls Home < 2 Mi To West Point! - Peekskill, NY
10 13 reviews

Charming Highland Falls Home < 2 Mi To West Point!

apartment, Highland Falls
This Highland Falls vacation home is located less than a mile from the United States Military Academy and Bear Mountain State Park, offering easy access to historical sites and outdoor recreation.
This 1740-square-foot house features six bedrooms, three bathrooms, sleeps twelve guests, and includes amenities such as a fully equipped kitchen, air conditioning, free internet, and outdoor barbecue grills.
Cozy Retreat W/ Pool, Cinema Room & Fire Pit - Peekskill, NY
9.6 15 reviews

Cozy Retreat W/ Pool, Cinema Room & Fire Pit

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
9.9 127 reviews

Cozy Retreat W/ Pool, Cinema Room & Fire Pit

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.

Best Peekskill, NY vacation rentals with parking

Valley View Farm - Peekskill, NY
9.7 7 reviews

Valley View Farm

gîte, Lake Mohegan
Lovely 3br Home With Parking-walk To Wp Gate! - Peekskill, NY
10 7 reviews

Lovely 3br Home With Parking-walk To Wp Gate!

apartment, Highland Falls
Lake Retreat Farm Style W Kayak Bbq Patio Fire Pit - Peekskill, NY
10 5 reviews

Lake Retreat Farm Style W Kayak Bbq Patio Fire Pit

apartment, Lake Mohegan
Quiet Apt With Coffee Bar, 1/2 Mile To West Point! - Peekskill, NY
9.6 23 reviews

Quiet Apt With Coffee Bar, 1/2 Mile To West Point!

apartment, Highland Falls

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.

3br Near West Point | Coffee Bar | Sleeps 6 - Peekskill, NY
10 1 review

3br Near West Point | Coffee Bar | Sleeps 6

apartment, Highland Falls

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.

Charming Home In Peekskill Ny - Peekskill, NY
9.9 119 reviews

Charming Home In Peekskill Ny

apartment, Peekskill
Lakefront Sauna 1 Hr Nyc Near Cold Spring - Peekskill, NY
10 5 reviews

Lakefront Sauna 1 Hr Nyc Near Cold Spring

apartment, Lake Mohegan
Hudson Valley Home 50 Min From Nyc - Dog Friendly - Peekskill, NY
9.8 42 reviews

Hudson Valley Home 50 Min From Nyc - Dog Friendly

apartment, Lake Mohegan
Serene Mountain Top Views Overlooking Hudson River And Surrounding Highlands - Peekskill, NY
9.8 140 reviews

Serene Mountain Top Views Overlooking Hudson River And Surrounding Highlands

cottage, Fort Montgomery

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.

E And T Getaway Llc - Peekskill, NY
9.8 217 reviews

E And T Getaway Llc

apartment, Stony Point
The Abbey Inn & Spa - Peekskill, NY
No reviews

The Abbey Inn & Spa

resort, Peekskill
The Cottage At Oasis Cove - Peekskill, NY
9.8 35 reviews

The Cottage At Oasis Cove

house, Verplanck

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.

'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
Modern West Point House Near West Point - 3 Bed, 2 Bath With Hot Tub & Fire Pit! - Peekskill, NY
10 20 reviews

Modern West Point House Near West Point - 3 Bed, 2 Bath With Hot Tub & Fire Pit!

apartment, Highland Falls
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