Holiday Rentals in Peekskill, NY

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

Peekchill: Walk To Coffeehouse & Forest - Peekskill, NY
9.6 38 reviews

Peekchill: Walk To Coffeehouse & Forest

apartment, Peekskill
This Peekskill house, situated on a quiet street only 0.32 km from the Blue Mountain Reservation and within walking distance of Depew Park and the Metro-North station, offers easy access to hiking trails and local amenities.
Sleeping six guests across two bedrooms and two bathrooms, this two-storey property boasts a modern kitchen with appliances including a washer-dryer, a spacious garden, and an electric fireplace; nearby attractions include the Hudson River boat launches.
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 holiday home is situated less than 1.6km from the United States Military Academy and Bear Mountain State Park, offering easy access to West Point and its historical attractions.
This six-bedroom property boasts 162 square metres of floor space, sleeping up to 12 guests comfortably, and includes a fully equipped kitchen, barbecue facilities, and a DVD player.
Gloves Off Retreat  A Quiet Hudson Valley Escape - Peekskill, NY
10 4 reviews

Gloves Off Retreat A Quiet Hudson Valley Escape

apartment, Peekskill
This Garrison flat offers a secluded escape on 1.6 private acres, approximately 96 kilometres north of New York City via car or Metro-North, with convenient access to Breakneck Ridge, Anthony's Nose, Bear Mountain State Park, and the riverside towns of Cold Spring and Beacon.
This pet-friendly, family-friendly dwelling for four features two bathrooms, a modern kitchen, air conditioning, and internet, with subtle boxing-inspired touches complementing its blend of modern comfort and vintage style for a peaceful retreat.
West Point At Your Doorstep! Walk To Academy  Mountain Views  Easy Parking - Peekskill, NY
9.4 29 reviews

West Point At Your Doorstep! Walk To Academy Mountain Views Easy Parking

apartment, Highland Falls
This apartment is located in Highland Falls, just a 10-minute walk from the United States Military Academy, the Hudson River, and the West Point Museum, making it a great base for exploring the area. It has received excellent user ratings, so you can be sure of a comfortable and enjoyable stay.
The apartment has two bedrooms and one bathroom, covering 84 square metres and accommodating up to six guests. It includes a fully equipped kitchen, air conditioning, parking, internet access, and a spa, offering everything you need for a relaxing and convenient stay.

Best Peekskill, NY holiday rentals with parking

Updated Home W/ Patio Half Mile To West Point - Peekskill, NY
9.8 71 reviews

Updated Home W/ Patio Half Mile To West Point

house, Highland Falls
This charming three-bedroom house in Highland Falls is located just 800 metres from West Point and 14 kilometres from Bear Mountain State Park, offering easy access to a range of attractions and activities. The property has consistently received excellent reviews for its cleanliness, location, and overall experience.
The 102 square metre property comfortably accommodates up to six guests and boasts a fully equipped kitchen, a relaxing patio, air conditioning, and free Wi-Fi, ensuring a comfortable and enjoyable stay. Guests can enjoy the peaceful setting of Highland Falls, take advantage of the nearby hiking and biking trails, or explore the historical grounds of West Point.
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.
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.
Highlands Retreat - Peekskill, NY
10 8 reviews

Highlands Retreat

apartment, Highland Falls
This four-bedroom flat, located on the historic J.P. Morgan Estate in Highland Falls, offers convenient access, being just over 3 kilometres from the West Point gate and across the street from a wooded preserve.
This accommodation for seven guests features a fully equipped kitchen, separate dining room, an outdoor patio with a gas grill, complimentary coffee and teas, and free off-street parking for up to three vehicles, with walking access to hiking trails including Mount Beacon and Storm King Mountain.

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.

Popular destinations

Best Peekskill, NY holiday rentals with a balcony

Scenic & Serene: 3br/3ba W Panoramic Hudson Views! A Birder's Paradise - Peekskill, NY
8.8 3 reviews

Scenic & Serene: 3br/3ba W Panoramic Hudson Views! A Birder's Paradise

apartment, Croton-on-Hudson
This four-bedroom flat in Croton-on-Hudson, New York, is located near Van Cortlandt Manor and Sing Sing Correctional Facility.
This property offers WiFi, air conditioning, and a kitchen with a microwave and dishwasher, accommodating up to eight guests with four queen beds, and is close to the Westchester Skating Academy and Manitoga The Russel Wright Design Center.
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.
Cozy 3bedroom Home In Highland Falls, Only A Five-minute Walk From West Point Ny - Peekskill, NY
9.6 4 reviews

Cozy 3bedroom Home In Highland Falls, Only A Five-minute Walk From West Point Ny

apartment, Highland Falls
This Highland Falls flat offers excellent proximity to the United States Military Academy at West Point and Thayer, located just 800 metres away, and is 8.4 kilometres from Bear Mountain State Park.
This three-bedroom, two-bathroom accommodation for six guests includes a microwave oven, dishwasher, air conditioning, and parking, with easy access to local attractions such as Fort Putnam, Manitoga The Russel Wright Design Center, Woodbury Common Premium Outlets, and entertainment at Monteverde at Oldstone.
*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 three-bedroom apartment, situated just an hour from New York City and ten minutes from West Point, offers a serene mountain escape with stunning views. It has received excellent ratings for its location, cleanliness, and overall experience.
The apartment features a spacious living area with a large lounge and game room, ideal for family gatherings or entertaining guests. Enjoy the peace and privacy of the five-acre property, equipped with a heated swimming pool, all-year hot tub, and a spacious deck, perfect for relaxing and taking in the scenic surroundings.

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.
Yacht At Dock - On The Waterfront! - Peekskill, NY
9.6 6 reviews

Yacht At Dock - On The Waterfront!

boat, West Haverstraw
This yacht is docked in Stoney Point, just a short distance upriver from West Haverstraw, offering stunning views of the Hudson River and the New York City skyline. The property has consistently received excellent ratings for location, cleanliness, and user experience.
The vessel comfortably accommodates four guests in two bedrooms, each with its own bathroom. Amenities include a fully equipped kitchen, Wi-Fi access, and a spacious deck perfect for enjoying the fresh air and views.
Luxury Lake House Sauna 1h From Nyc - Peekskill, NY
10 182 reviews

Luxury Lake House Sauna 1h From Nyc

apartment, Lake Mohegan
This lakeside apartment near Lake Mohegan, New York, offers private lakefront access with a dock, and is conveniently located approximately 32 kilometres from West Point and Bear Mountain, and 80 kilometres from New York City.
The self-catering property sleeps four guests and boasts an 86-inch TV, a large deck overlooking the lake, heated bathroom floors, and a free Tesla charger (adapter available for other EVs).
Secluded Mid-century Modern Home 4 Bedroom - Peekskill, NY
9.7 32 reviews

Secluded Mid-century Modern Home 4 Bedroom

apartment, Croton-on-Hudson
This four-bedroom home is situated in Croton-on-Hudson, close to the Croton Dam and 24 kilometres from West Point, offering a peaceful retreat just a short distance from the bustling city. The apartment has received excellent ratings for location, cleanliness, and overall experience.
The property comfortably accommodates six guests and includes a fully equipped kitchen with a fridge, freezer, and dishwasher. Amenities such as air conditioning, a garden, a fitness centre, and parking are provided, along with easy access to nearby attractions and recreational activities.
©2026 cozycozy.com