Holiday Rentals in Peekskill, NY

19 available vacation rental offers

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Peekskill, NY holiday rentals
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Best Holiday rentals and Airbnb offers in Peekskill, NY

Best family friendly Peekskill, NY holiday rentals

Among the 19 accommodations in Peekskill, NY, here are the 3 best family friendly rentals

Cozy Retreat W/ Pool, Cinema Room & Fire Pit - Peekskill, NY
9.9 122 reviews
Peekskill, NY
11/09 – 13/09
SG$1860/nighttotal: SG$3720 (2 )

Cozy Retreat W/ Pool, Cinema Room & Fire Pit

1 8
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.
Bear Mtn Haus Near Hiking Trails - Peekskill, NY
9.7 136 reviews
Peekskill, NY
11/09 – 13/09
SG$1367/nighttotal: SG$2734 (2 )

Bear Mtn Haus Near Hiking Trails

1 8
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 Hudson Valley 3-bedroom Family Getaway - Peekskill, NY
Peekskill, NY
11/09 – 13/09
SG$749/nighttotal: SG$1498 (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.

Best Peekskill, NY holiday rentals with parking

Castle Retreat W/ Pool, Bbq, Game Room & Pets Ok! - Peekskill, NY
9.2 7 reviews
Peekskill, NY
11/09 – 13/09
SG$2094/nighttotal: SG$4188 (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.

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.

Destinations nearby

Best Peekskill, NY holiday rentals with a balcony

Castle Retreat W/ Pool, Bbq, Game Room & Pets Ok! - Peekskill, NY
9.2 7 reviews
Peekskill, NY
11/09 – 13/09
SG$2094/nighttotal: SG$4188 (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
SG$1209/nighttotal: SG$2418 (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.
Charming Hudson Valley 3-bedroom Family Getaway - Peekskill, NY
Peekskill, NY
11/09 – 13/09
SG$749/nighttotal: SG$1498 (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.
Storm King Lodge - Storm King Art Center, West Point, Woodbury Commons Outlets - Peekskill, NY
9.6 5 reviews
Peekskill, NY
11/09 – 13/09
SG$1872/nighttotal: SG$3744 (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 holiday rentals

Among the 19 accommodations in Peekskill, NY, here are the 4 best pet friendly rentals

Cozy Retreat W/ Pool, Cinema Room & Fire Pit - Peekskill, NY
9.6 15 reviews
Peekskill, NY
11/09 – 13/09
SG$1892/nighttotal: SG$3784 (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.
Welcome Spring Estate An Hr From Nyc - Peekskill, NY
10 108 reviews
Peekskill, NY
11/09 – 13/09
SG$4343/nighttotal: SG$8686 (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.
Cozy Retreat W/ Pool, Cinema Room & Fire Pit - Peekskill, NY
9.9 122 reviews
Peekskill, NY
11/09 – 13/09
SG$1860/nighttotal: SG$3720 (2 )

Cozy Retreat W/ Pool, Cinema Room & Fire Pit

1 8
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.
Castle Retreat W/ Pool, Bbq, Game Room & Pets Ok! - Peekskill, NY
9.2 7 reviews
Peekskill, NY
11/09 – 13/09
SG$2094/nighttotal: SG$4188 (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.
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