Holiday Rentals in Peekskill, NY

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Peekskill, NY holiday rentals
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29 Holiday rentals and Airbnb in Peekskill, NY

Best family friendly Peekskill, NY holiday rentals

Among the 29 accommodations in Peekskill, NY, here are the 4 best family friendly rentals

Cherry Blossom Lake House - Peekskill, NY
10 1 review

Cherry Blossom Lake House

house, Lake Mohegan
This spacious three-bedroom detached house, located in Lake Peekskill, offers lake views and is situated 22.5 kilometres from Bear Mountain State Park and 33.8 kilometres from Metro-North Harriman Station.
This air-conditioned property spans 139 square metres, accommodates up to 11 guests with three bedrooms and two bathrooms, and features a kitchen with a fridge, microwave oven, and dishwasher, alongside a terrace, garden, jacuzzi, sauna, and parking.
Bear Mountain House. - Peekskill, NY
10 16 reviews

Bear Mountain House.

apartment, Fort Montgomery
This Garrison cottage is located on the mountainside with partial Hudson River views, just minutes from the Bear Mountain Bridge and a short drive to Cold Spring shops and restaurants. The property has excellent user ratings, making it a popular choice for travellers. This comfortable home has three bedrooms and three bathrooms, accommodating up to eight guests. The house offers a range of amenities, including a fully equipped kitchen, a terrace with outdoor furniture, a garden, and parking.
Serene Pond Side Retreat Getaway Near West Point - Peekskill, NY
10 5 reviews

Serene Pond Side Retreat Getaway Near West Point

house, Fort Montgomery
This 3-bedroom, 2-bathroom flat is located in Fort Montgomery, offering a peaceful retreat with easy access to historic Fort Montgomery, just 500 metres away, and scenic walking trails.
This apartment accommodates up to 6 guests and features a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, alongside air conditioning, a fitness centre, and parking.
Arkadia House
Mid-century Retreat With Pool & View - Peekskill, NY
9.9 46 reviews

Arkadia House Mid-century Retreat With Pool & View

apartment, Highland Falls
This Highland Falls apartment boasts a superb Hudson Riverfront location, minutes (a few kilometres) from Cold Spring, West Point, and Beacon, offering easy access to Bear Mountain State Park.
The three-bedroom, two-bathroom dwelling sleeps six, features a private pool overlooking the river, and includes amenities such as a fridge, dishwasher, air conditioning, and parking; guests can enjoy the on-site garden and excellent on-site facilities.

Best Peekskill, NY holiday rentals with parking

Magical Forest Dome Near Nyc - Peekskill, NY
10 4 reviews

Magical Forest Dome Near Nyc

bubble, Peekskill
This unique bubble is located in a private woodland setting just 80 kilometres north of Manhattan, near Peekskill, offering a secluded escape from the city. The geodesic dome sleeps up to four guests in two king-sized beds, providing a comfortable and unusual stay. The bubble features a full kitchen, a fire pit for stargazing, and both indoor and outdoor showers, allowing guests to enjoy the peace and quiet of the surrounding woodland.
Spectacular River& Mountain Views Near West Point! - Peekskill, NY
10 58 reviews

Spectacular River& Mountain Views Near West Point!

apartment, Fort Montgomery
This apartment is located in Fort Montgomery, just an hour outside of New York City, offering stunning views of the Hudson River and surrounding mountains. It has received excellent ratings for its location, cleanliness, and overall experience.
The apartment has three bedrooms and three bathrooms, comfortably accommodating up to eight guests. It features a modern kitchen with a fridge, freezer, microwave oven, and dishwasher, along with a private deck, backyard, and a scenic hike trail, perfect for exploring the surrounding natural beauty.
Bear Mtn Haus Near Hiking Trails - Peekskill, NY
9.7 139 reviews

Bear Mtn Haus Near Hiking Trails

apartment, Fort Montgomery
This Garrison cottage is located on the mountainside with partial Hudson River views, just a short drive from the Bear Mountain Bridge and 60 minutes from NYC. The property has received excellent ratings for its location, cleanliness, and overall experience.
The three-bedroom, three-bathroom home comfortably accommodates eight guests. It features a well-equipped kitchen with a fridge, microwave oven, and dishwasher, as well as air conditioning, a garden, and parking. Guests can enjoy breathtaking scenery, access nearby hiking trails, and take advantage of the private terrace with wildlife viewing.
Charming Studio Apartment - Peekskill, NY
9.9 55 reviews

Charming Studio Apartment

apartment, Peekskill
This Cortlandt Manor studio apartment, a short 8-16 km drive from Peekskill's downtown area and the NY Presbyterian Hudson Valley Hospital, offers easy access to the Annsville Creek Preserve and Blue Mountain Reservation walking/biking trails.
The self-contained flat features a queen-size bed, a well-equipped kitchen with a Keurig coffee maker, a private deck with BBQ, on-site laundry facilities, keyless entry, designated parking, and accommodates two guests, perfect for exploring Peekskill and its surrounding attractions.

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.

Popular destinations

Best Peekskill, NY holiday rentals with a balcony

Croton Quarters - Comfortable Apartments, Nyc Close - Peekskill, NY
10 20 reviews

Croton Quarters - Comfortable Apartments, Nyc Close

apartment, Croton-on-Hudson
Croton Quarters apartments are located in Croton-on-Hudson, New York, approximately 27 kilometres from Westchester County Airport, 29 kilometres from the Palisades Center mall, and 31 kilometres from Manhattanville College.
This two-bedroom, one-bathroom flat offers self-catering facilities including a dishwasher and microwave, sleeps seven guests, and boasts a terrace, garden, and free parking, with family-friendly amenities such as outdoor play equipment nearby.
Comfortable 2bd - Convenience & Style - 45min To Nyc - Great Food - Peekskill, NY
9.8 93 reviews

Comfortable 2bd - Convenience & Style - 45min To Nyc - Great Food

apartment, Croton-on-Hudson
This family-friendly flat is located in Croton-on-Hudson, within easy reach of several parks and historical sites, including Croton Landing Park and Van Cortlandt Manor. It has consistently received excellent guest reviews.
The 74 square metre apartment has two bedrooms and can comfortably accommodate up to four guests. The property offers a range of amenities, including a fully equipped kitchen, a terrace, a garden, and free Wi-Fi, ensuring a pleasant and convenient stay.
'Croton Nook' - Spacious Studio With Full Eat-in Kitchen, Cozy Getaway - Peekskill, NY
10 2 reviews

'Croton Nook' - Spacious Studio With Full Eat-in Kitchen, Cozy Getaway

studio, Croton-on-Hudson
This Croton-on-Hudson first-floor apartment is conveniently located near the train station, offering easy access to local cafes, restaurants, and a supermarket, and is approximately 72km from New York City.
The 56-square-metre self-contained studio sleeps up to three guests and boasts a private entrance, terrace, garden access, a fully equipped kitchen including a dishwasher, plus free on-site parking and Wi-Fi; explore nearby attractions such as the United States Military Academy at West Point and the Sing Sing Correctional Facility Museum.
Lakefront Escape  Sauna  1 Hr From Nyc 3 Spacious Bedrooms - Peekskill, NY
No reviews

Lakefront Escape Sauna 1 Hr From Nyc 3 Spacious Bedrooms

apartment, Lake Mohegan
This lakefront residence offers direct access to Lake Peekskill, situated in the Hudson Valley, approximately 1 hour from New York City and a short drive to Cold Spring, Beacon, and West Point.
This 139 square metre apartment sleeps 6 guests across 3 bedrooms and 2 bathrooms, featuring a fully equipped kitchen with microwave and dishwasher, air conditioning, jacuzzi, terrace, garden, sauna, and parking, with a coffee bar and Samsung Frame TV for entertainment.

Best pet friendly Peekskill, NY holiday rentals

Among the 29 accommodations in Peekskill, NY, here are the 4 best pet friendly rentals

Modern Country Cottage By Bear Mountain - Peekskill, NY
9.9 225 reviews

Modern Country Cottage By Bear Mountain

apartment, Highland Falls
This charming cottage is situated in the Hudson Valley, just outside Fort Montgomery, surrounded by 4 hectares of beautiful countryside. It has received excellent ratings for its location, cleanliness, and overall experience.
The cottage has one bedroom and one bathroom, comfortably accommodating up to three guests. It features a spacious living area with a wood-panelled ceiling and skylights, a private garden, and a picnic area with a grill for enjoying meals outdoors.
Beautiful First Flr, 2-bedroom Apt W/ Free Parking - Peekskill, NY
10 7 reviews

Beautiful First Flr, 2-bedroom Apt W/ Free Parking

apartment, Highland Falls
This Highland Falls ground-floor flat is conveniently located one block from Main Street's restaurants and a short walk from the United States Military Academy at West Point.
The 93 square metre (approximately 1000 square feet) self-catering apartment sleeps six, featuring two bedrooms, one bathroom, a fully equipped kitchen, in-unit laundry, free Wi-Fi, and designated parking.
Discover Natures Glory!  Perfect Family Home - Peekskill, NY
9.8 131 reviews

Discover Natures Glory! Perfect Family Home

apartment, Fort Montgomery
This three-bedroom house is located on the road into Fort Montgomery, just a short distance from the town's main attractions, Bear Mountain, and hiking trails. The accommodation has excellent ratings for location, cleanliness, and user experience, making it a great choice for families and groups.
The house can comfortably accommodate up to eight guests and features a spacious living room, a fully equipped kitchen, a garden, and parking. Guests can enjoy modern amenities, including air conditioning, internet access, and a washing machine, as well as a peaceful setting close to nature.
Discover Natures Glory! Perfect Family Home - Peekskill, NY
8.8 6 reviews

Discover Natures Glory! Perfect Family Home

apartment, Fort Montgomery
This Highland Falls apartment, near Fort Montgomery, offers easy access to local restaurants and shops, and is a 19km drive from the United States Military Academy at West Point.
Sleeping eight guests, this three-bedroom property features two double bedrooms, one with bunk beds, a fully equipped kitchen, free on-site parking, and a terrace/balcony with garden access; pets are welcome.
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