Compare Vacation Rentals & Airbnb in Peekskill, NY

29 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • priceline
  • tripadvisor
  • tripcom
  • sonder
  • homestay
  • hostelworld
  • hotelscom
  • agoda
Peekskill, NY vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

29 Rentals and Airbnb in Peekskill, NY

Best family friendly Peekskill, NY vacation 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.
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
This apartment is situated in a peaceful private community in the Hudson Valley, just 15 kilometres from Bear Mountain and Fahnestock State Park, offering easy access to the region's beautiful hiking trails. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
This charming self-catering home can accommodate up to 5 guests, and features a modern, cosy living space with a fireplace, a large deck, and a backyard. Enjoy the convenience of a fully equipped kitchen, a washing machine and dryer, and a dedicated desk/office area, perfect for work or leisure.
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 the picturesque town of Cold Spring in the Hudson Valley. It has consistently received excellent ratings for its location, cleanliness, and overall experience, making it a popular choice for families and groups.
The house offers three bedrooms and three bathrooms, comfortably accommodating up to eight guests. Amenities include a fully equipped kitchen, air conditioning, a swimming pool, a garden, and a pool table in the lower floor, providing plenty of space for relaxation and entertainment.
Cozy Retreat W/ Pool, Cinema Room & Fire Pit - Peekskill, NY
9.6 16 reviews

Cozy Retreat W/ Pool, Cinema Room & Fire Pit

cottage, Lake Mohegan
This charming cottage is located just a short drive from the bustling town of Cold Spring, offering a peaceful retreat in the woods of Putnam Valley. The property has been highly rated by previous guests, receiving excellent reviews for its comfortable accommodation and tranquil setting.
The cottage offers three bedrooms and three bathrooms, comfortably sleeping up to eight guests. It is equipped with a range of amenities including a fully equipped kitchen, a swimming pool, a Jacuzzi, and a private deck with stunning views of the Hudson Valley.

Best Peekskill, NY vacation 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.
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.
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.
Summer In Garrison - Victorian Escape - 1 Hr Nyc - Peekskill, NY
9.3 3 reviews

Summer In Garrison - Victorian Escape - 1 Hr Nyc

apartment, Highland Falls
This Victorian farmhouse, located in Garrison, NY, offers a 3-bedroom, 2.5-bathroom rental just 5 minutes from the train station and 10 minutes from Cold Spring, providing convenient access to Highland Falls and its surroundings.
The 3.6-acre property features direct access to Hudson Valley hiking trails, a heated writing studio, and is within walking distance of farm-to-table restaurants, accommodating up to 4 guests.

Frequently Asked Questions about vacation rentals in Peekskill, NY

  • What should a first-time visitor not miss in Peekskill, NY?

    For a first-timer, you definitely want to check out the historic Hudson River Museum, which has a great collection of art and local history. Also, take a walk along the Peekskill waterfront and enjoy the views of the river. And if you're a history buff, you can't miss the dramatic ruins of the 18th-century Van Cortlandt Manor.
  • 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 near the waterfront is a popular choice for vacation rentals. It's close to all the action, with restaurants, shops, and the train station just a short walk away.
  • 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 is always a hit with families, with interactive exhibits and plenty of space to run around. The Peekskill Farmers Market is a great place to spend a Saturday morning, with fresh produce and local crafts.
  • 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 usually during the spring and fall, when the weather is mild and the crowds are smaller. You'll find some great deals during the shoulder seasons, too.
  • 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 lively events calendar, with the Riverfront Greenmarket happening every Saturday from June to October, and the Peekskill Jazz Festival in July. The Hudson Valley Renaissance Festival is just a short drive away, too.
  • 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 Hudson River Walkway is free and offers stunning views. The Peekskill Public Library is a great place to spend a rainy afternoon, and it's completely free to visit.
  • What are the best restaurants with local dishes in Peekskill, NY?

    For a taste of local cuisine, try The Peekskill Brewery for their delicious craft beers and pub fare. The Smokehouse BBQ is another favourite, with mouthwatering smoked meats and Southern-style sides.
  • What are the best walking or cycling routes in Peekskill, NY?

    The Hudson River Walkway is a paved path that stretches for miles along the river, perfect for a leisurely walk or bike ride. The Peekskill Riverfront Park is also a great spot for a walk or bike ride.
  • Are there pet-friendly attractions in Peekskill, NY?

    Many of the parks and trails in Peekskill are dog-friendly, including the Hudson River Walkway and the Peekskill Riverfront Park. The Peekskill Farmers Market also welcomes well-behaved dogs.
  • What are the benefits of choosing a vacation rental in Peekskill, NY?

    Vacation rentals offer more space and privacy than hotels, and they're often a more affordable option for families or groups. You'll also have access to a kitchen, which can help you save money on dining out.
  • What are the top sports attractions and facilities in Peekskill, NY?

    Peekskill has several parks with sports facilities, including the Peekskill Riverfront Park, which has basketball courts, tennis courts, and a playground. The Peekskill High School also has a large athletic field.

Popular destinations

Best Peekskill, NY vacation rentals with a balcony

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 rural property, a farm, is located in Putnam Valley, offering easy access to the United States Military Academy, which is 4.5 kilometres away, and Boscobel House and Gardens, 10.2 kilometres distant.
This farm provides accommodation for up to 8 guests with 2 bedrooms and 3 bathrooms, featuring air conditioning, an in-room kitchen, and on-site laundry facilities, with the added benefit of a garden and proximity to the Hudson Valley Center for Contemporary Art and Willow Ridge Farm for evening entertainment.
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.
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.
'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.

Best pet friendly Peekskill, NY vacation rentals

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

Modern, Sun-filled Farmhouse Retreat - Peekskill, NY
10 27 reviews

Modern, Sun-filled Farmhouse Retreat

apartment, Highland Falls
This three-bedroom, two-bathroom apartment in Garrison, New York, is situated a short 6.4km drive from Cold Spring and a mere 2.6km from Garrison Metro-North station, providing easy access to New York City.
The self-catering property sleeps seven, boasts a chef's kitchen, fireplace, central air conditioning, Wi-Fi, parking, and pet-friendly accommodation near the Appalachian Trail, ideal for hiking and exploring the surrounding woodland.
Lakefront Sauna 1 Hr Nyc Near Cold Spring - Peekskill, NY
10 5 reviews

Lakefront Sauna 1 Hr Nyc Near Cold Spring

apartment, Lake Mohegan
This Putnam Valley flat offers direct lake access and is situated approximately 160 kilometres from NYC, 32 kilometres to Cold Spring, 48 kilometres to Beacon & West Point, and 9.6 kilometres to Main Street dining.
This lakeside dwelling accommodates six guests with three bedrooms and two bathrooms, featuring a fully equipped kitchen, air conditioning, a Jacuzzi, a garden, and direct private lakefront access, with optional seasonal hot tub and year-round wood-burnt sauna available for an additional fee.
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.
©2026 cozycozy.com