Compare Vacation Rentals & Airbnb in Peekskill, NY

19 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

19 Rentals and Airbnb in Peekskill, NY

Best family friendly Peekskill, NY vacation rentals

Among the 19 accommodations in Peekskill, NY, here are the 2 best family friendly rentals

Cozy Retreat W/ Pool, Cinema Room & Fire Pit - Peekskill, NY
9.6 15 reviews
Peekskill, NY
11/09 – 13/09
$2057/nighttotal: $4114 (2 )

Cozy Retreat W/ Pool, Cinema Room & Fire Pit

3 8
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.
Bear Mountain House. - Peekskill, NY
10 15 reviews
Peekskill, NY
11/09 – 13/09
$1315/nighttotal: $2630 (2 )

Bear Mountain House.

3 8
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.

Best Peekskill, NY vacation rentals with parking

Green Country House Garrison - Peekskill, NY
9.9 33 reviews
Peekskill, NY
11/09 – 13/09
$852/nighttotal: $1704 (2 )

Green Country House Garrison

1 8
apartment , Highland Falls
This three-bedroom apartment is located in a secluded area of Peekskill, offering privacy and quiet while still being within easy reach of the city's attractions. It has received excellent ratings for location, cleanliness, and user experience.
The apartment comfortably accommodates up to eight guests and features a fully equipped kitchen with a fridge, freezer, microwave oven, and dishwasher. It also boasts a garden, fitness centre, parking, air conditioning, and security cameras for added peace of mind.
Bear Mountain House. - Peekskill, NY
10 15 reviews
Peekskill, NY
11/09 – 13/09
$1315/nighttotal: $2630 (2 )

Bear Mountain House.

3 8
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.
Cozy Retreat W/ Pool, Cinema Room & Fire Pit - Peekskill, NY
9.6 15 reviews
Peekskill, NY
11/09 – 13/09
$2057/nighttotal: $4114 (2 )

Cozy Retreat W/ Pool, Cinema Room & Fire Pit

3 8
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.
Charming Hudson Valley 3-bedroom Family Getaway - Peekskill, NY
Peekskill, NY
11/09 – 13/09
$814/nighttotal: $1628 (2 )

Charming Hudson Valley 3-bedroom Family Getaway

1 8
house , Stony Point
This Stony Point house, located in Tomkins Cove, is 16km from Bear Mountain State Park and 21km from The Palisades Center mall, offering easy access to both attractions.
The 121-square-metre property boasts one bedroom, one bathroom, sleeps fifteen guests, and includes a fully equipped kitchen, private terrace, free Wi-Fi, and free parking.

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.

Destinations nearby

Best Peekskill, NY vacation rentals with a balcony

Charming 2-bedroom Farmhouse With Ac In Putnam Valley - Peekskill, NY
Peekskill, NY
11/09 – 13/09
$714/nighttotal: $1428 (2 )

Charming 2-bedroom Farmhouse With Ac In Putnam Valley

2 8
farm , 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.
Castle Retreat W/ Pool, Bbq, Game Room & Pets Ok! - Peekskill, NY
9.2 7 reviews
Peekskill, NY
11/09 – 13/09
$2277/nighttotal: $4554 (2 )

Castle Retreat W/ Pool, Bbq, Game Room & Pets Ok!

5 8
apartment , Ossining
This family-friendly holiday home in Ossining is situated a 15-minute walk from Sing Sing Correctional Facility and a 12-minute walk from Old Croton Aqueduct State Park.
Boasting 398 square meters of living space, this accommodation accommodates up to 13 guests with 5 bedrooms and 4 bathrooms, featuring a private swimming pool, garden, billiards, and free Wi-Fi, with on-site covered parking and proximity to outdoor activities.
Bear Mountain House. - Peekskill, NY
10 15 reviews
Peekskill, NY
11/09 – 13/09
$1315/nighttotal: $2630 (2 )

Bear Mountain House.

3 8
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.
Storm King Lodge - Storm King Art Center, West Point, Woodbury Commons Outlets - Peekskill, NY
9.6 5 reviews
Peekskill, NY
11/09 – 13/09
$2035/nighttotal: $4070 (2 )

Storm King Lodge - Storm King Art Center, West Point, Woodbury Commons Outlets

4 8
chalet , Firthcliffe
Storm King Lodge, a country house, is located in Mountainville, New York, within the Lower Hudson River Valley, approximately 97 kilometres from NYC and close to Storm King Art Centre and West Point.
This 279 square metre lodge offers 4 bedrooms and 4 bathrooms, accommodating up to 8 guests with its own kitchen, air conditioning, terrace, garden, and access to nearby hiking and cultural attractions.

Best pet friendly Peekskill, NY vacation rentals

Among the 19 accommodations in Peekskill, NY, here are the 1 best pet friendly rentals

Welcome Spring Estate An Hr From Nyc - Peekskill, NY
10 108 reviews
Peekskill, NY
11/09 – 13/09
$4722/nighttotal: $9444 (2 )

Welcome Spring Estate An Hr From Nyc

1 8
house , Croton-on-Hudson
This eight-bedroom Croton-on-Hudson estate, approximately 16km from the Metro-North offering easy access to Midtown Manhattan, sits on 9 hectares of private land adjoining 80 hectares of protected nature trails near the Teatown Lake Reservation and the Old Croton Aqueduct Trail.
The farmhouse, built circa 1895, boasts a gourmet kitchen, piano, library, expansive dining room, tennis court, lake for kayaking, and accommodates up to 16 guests, with the option of adding a cottage; nearby attractions include Bald Mountain and West Point.
©2026 cozycozy.com