Peekskill, NY holiday rentals

Holiday Rentals in Peekskill, NY

85 available vacation rental offers

2 1
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Best Holiday rentals and Airbnb offers in Peekskill, NY

Gorgeous Garrison Lake House Near Nyc! - Peekskill, NY
9.9Excellent 96 reviews
Peekskill, NY
2 3
SG$648/nighttotal: SG$4536 (7 )

Gorgeous Garrison Lake House Near Nyc!

apartment - Lake Mohegan
This lakefront home is located in Lake Mohegan, just an hour from New York City and a short drive from Cold Spring, West Point, and the Shakespeare Festival. The property has received excellent ratings for cleanliness, location, and user experience.
This three-bedroom dwelling can comfortably accommodate up to four guests. Enjoy a spacious living room with a fireplace, a fully equipped kitchen, a screened-in porch with a BBQ, and a private lakefront setting with stunning views.
*Forest Retreat* Rustic Luxury Near Bear Mt Hiking - Peekskill, NY
9.8Excellent 62 reviews
Peekskill, NY
2 3
SG$1603/nighttotal: SG$11221 (7 )

*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.
The Charming Black Barn Minutes From West Point - Peekskill, NY
10Excellent 9 reviews
Peekskill, NY
2 3
SG$1176/nighttotal: SG$8232 (7 )

The Charming Black Barn Minutes From West Point

apartment - Fort Montgomery
This charming apartment is situated just off Route 9D in Fort Montgomery, a short drive from the Bear Mountain Bridge and Manitou Point Preserve, making it a great base for exploring the scenic Hudson Valley. It has received excellent ratings for its cleanliness, location, and overall experience, ensuring a comfortable and enjoyable stay.
The apartment, a converted barn designed by renowned architect Edward Knowles, offers a unique and spacious layout, comfortably accommodating up to eight guests. Enjoy access to a heated pool, a large screened-in porch, a fire pit, and a peaceful garden, providing ample opportunities for relaxation and entertainment.
Cozy 3 Bedroom House On Quiet Private Road - Peekskill, NY
9.8Excellent 107 reviews
Peekskill, NY
2 3
SG$395/nighttotal: SG$2765 (7 )

Cozy 3 Bedroom House On Quiet Private Road

apartment - Peekskill
This three-bedroom house is situated on a peaceful private road overlooking a creek, just a short distance from the Metro North Railroad and the Hudson River. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The home comfortably accommodates up to six guests and features a well-equipped kitchen with a fridge, freezer, microwave oven, and dishwasher. You can enjoy the peace and quiet of the creekside setting, explore nearby attractions, or take advantage of the on-site garden.
West Point Hudson Valley Getaway - Peekskill, NY
9.9Excellent 47 reviews
Peekskill, NY
2 3
SG$716/nighttotal: SG$5012 (7 )

West Point Hudson Valley Getaway

apartment - Highland Falls
This charming apartment is situated in the Ondaora Park community, just a short distance from Thayer Gates, offering easy access to West Point. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The apartment is a spacious home that can comfortably accommodate up to six guests. It features a well-equipped kitchen, a comfortable living area, and access to a swimming pool, garden, and parking.
Bear Mountain House. - Peekskill, NY
9.8Excellent 13 reviews
Peekskill, NY
2 3
SG$1001/nighttotal: SG$7007 (7 )

Bear Mountain House.

house - 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.
Bear Mtn Haus Near Hiking Trails - Peekskill, NY
9.7Excellent 120 reviews
Peekskill, NY
2 3
SG$483/nighttotal: SG$3381 (7 )

Bear Mtn Haus Near Hiking Trails

- 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.
Stay In The Heart Of West Point~walk 2 Mins To Academy! - Peekskill, NY
9.6Excellent 307 reviews
Peekskill, NY
2 2
SG$399/nighttotal: SG$2793 (7 )

Stay In The Heart Of West Point~walk 2 Mins To Academy!

apartment - Highland Falls
This apartment is situated in Highland Falls, just a 10-minute walk from the United States Military Academy, the Hudson River, and West Point Museum. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The apartment has two bedrooms and one bathroom, providing ample space for up to six guests. It includes a fully equipped kitchen, a dining area, a Smart TV, and a garden, making it ideal for a comfortable and enjoyable stay.
Secluded Mountain Top Horse Property Near W. Point - Peekskill, NY
9.9Excellent 188 reviews
Peekskill, NY
2 2
SG$442/nighttotal: SG$3094 (7 )

Secluded Mountain Top Horse Property Near W. Point

gîte - Fort Montgomery
This charming gîte is located on a secluded horse farm in the Hudson Valley, just a short drive from West Point and a 50-minute journey from New York City. It has received excellent ratings for its location, cleanliness, and overall experience.
The cottage has two bedrooms and one bathroom, comfortably accommodating up to six guests. Amenities include a fully equipped kitchen, air conditioning, a garden, and parking, as well as the opportunity to enjoy fresh eggs, organic vegetables, and the company of farm animals.
West Point/bear Mountain/hudson Valley Getaway - Peekskill, NY
10Excellent 92 reviews
Peekskill, NY
2 1
SG$267/nighttotal: SG$1869 (7 )

West Point/bear Mountain/hudson Valley Getaway

- Fort Montgomery
This newly created apartment is located in Fort Montgomery, New York, just minutes from West Point and Bear Mountain, offering easy access to the Hudson Valley's scenic attractions. It has received excellent ratings for its location, cleanliness, and overall experience.
The apartment is a spacious one-bedroom suite, comfortably accommodating up to four guests. It features a large patio, a 55-inch LED TV, and is close to restaurants, wineries, breweries, and shopping options, making it ideal for exploring the area.
Modern 4 Bedroom Home Near West Point & Bear Mt. - Peekskill, NY
10Excellent 33 reviews
Peekskill, NY
2 3
SG$657/nighttotal: SG$4599 (7 )

Modern 4 Bedroom Home Near West Point & Bear Mt.

- Fort Montgomery
This 4-bedroom house is located in the Hudson Valley, just a short drive from Thayer Gate, Bear Mountain State Park, and Woodbury Common Shopping Outlets, offering a peaceful retreat in a scenic setting. The property has received excellent reviews for its location, cleanliness, and overall experience.
The house comfortably accommodates families and groups of friends, providing a spacious and relaxing environment. Guests can enjoy a fully equipped kitchen, a private garden with an outdoor dining area, a fire pit, and a BBQ, making it ideal for both indoor and outdoor activities.
❤️😍 Cozy Studio Apartment In Quiet Neighborhood 🥰❤️ - Peekskill, NY
9.9Excellent 72 reviews
Peekskill, NY
2 1
SG$225/nighttotal: SG$1575 (7 )

❤️😍 Cozy Studio Apartment In Quiet Neighborhood 🥰❤️

studio - Highland Falls
This newly renovated studio apartment is located in a quiet cul-de-sac in Highland Falls, just a short walk from the Hudson River, Main Street, Bear Mountain State Park, and West Point Military Academy. It has consistently received excellent ratings from guests for its cleanliness, location, and overall experience.
The studio comfortably sleeps four guests and features a modern kitchen with granite countertops, a full-size bathroom, fast Wi-Fi, and a Smart TV. You can enjoy the private garden, relax in the Jacuzzi, and take advantage of the convenient parking.

Other types of accommodation in Peekskill, NY

Best Peekskill, NY holiday rentals with a pool

Among the 85 accommodations in Peekskill, NY, here are the 2 best rentals with a pool

Contemporary Barn In Prime Garrison - Peekskill, NY
9.3Excellent 14 reviews
Peekskill, NY
2 3
SG$576/nighttotal: SG$4032 (7 )

Contemporary Barn In Prime Garrison

- Highland Falls
This contemporary barn conversion is located in Garrison, just five minutes from the Garrison train station and a five-minute drive from Bear Mountain Park, offering a peaceful retreat close to nature and convenient access to nearby attractions. The property has received excellent user ratings for its location and overall experience, with a very good rating for cleanliness.
The spacious home features two living areas, a separate master suite with a bath, and a detached bunk room, comfortably accommodating up to six guests. Enjoy the expansive grounds with a swimming pool, tennis court, patio, and hiking trail, as well as modern amenities like a fully equipped kitchen and multiple bathrooms.
Charming Private Suite With Views Near The Hudson - Peekskill, NY
9.4Excellent 56 reviews
Peekskill, NY
2 1
SG$331/nighttotal: SG$2317 (7 )

Charming Private Suite With Views Near The Hudson

- Crugers
This private room and bathroom is located in a quiet, wooded area in Crugers, just a mile from the Hudson Valley and a 44-minute train ride from Grand Central Station in New York City. The accommodation has received excellent ratings for location, cleanliness and overall user experience.
The property has a private entrance and can accommodate up to two guests. Amenities include a small refrigerator, coffee machine, TV with cable and WiFi, parking, and a summer pool.

Best family friendly Peekskill, NY holiday rentals

Among the 85 accommodations in Peekskill, NY, here are the 3 best family friendly rentals

Private 2 Bdrm Apt In The Heart Of West Point-walk To Academy! - Peekskill, NY
9.0Excellent 4 reviews
Peekskill, NY
2 2
SG$506/nighttotal: SG$3542 (7 )

Private 2 Bdrm Apt In The Heart Of West Point-walk To Academy!

apartment - Highland Falls
This apartment is situated in West Point, just a short distance from the United States Military Academy and 8.3 miles from Bear Mountain State Park, offering easy access to both historical attractions and scenic outdoor activities. The apartment consistently receives excellent ratings for its location, cleanliness, and overall experience.
The apartment features two bedrooms and one bathroom, spread across 111 square metres of living space. Guests can enjoy a fully equipped kitchen, free Wi-Fi, private parking, and comfortable amenities such as parquet floors and a flat-screen TV.
Putnam Valley Vacation Rental: Patio & Lake Views! - Peekskill, NY
10Excellent 4 reviews
Peekskill, NY
2 3
SG$621/nighttotal: SG$4347 (7 )

Putnam Valley Vacation Rental: Patio & Lake Views!

cottage - Lake Mohegan
This three-bedroom cottage is located in Putnam Valley, just a mile from Lake Peekskill and a short drive from several state parks, including FDR State Park and Fahnestock State Park. The property has received excellent user ratings and is perfect for families or groups of up to seven guests.
The 111 square metre cottage has a fully equipped kitchen, two bathrooms, a comfortable living space, and a private garden. Guests can enjoy amenities such as free Wi-Fi, a gas grill, a fireplace, and a large patio with stunning lake views, making it an ideal choice for those seeking a relaxing retreat.
The Serene Quarters: 4 Minutes To West Point Academy, King Bed - Peekskill, NY
Peekskill, NY
2 3
SG$496/nighttotal: SG$3472 (7 )

The Serene Quarters: 4 Minutes To West Point Academy, King Bed

apartment - Highland Falls
This charming three-bedroom apartment is located in Highland Falls, just a short walk from the West Point Museum and the Hudson River, offering easy access to key landmarks and scenic views. The apartment is perfect for families or groups of up to eight guests, providing a comfortable and spacious retreat in a peaceful setting.
The apartment features a well-equipped kitchen, a comfortable living area with a smart TV, free Wi-Fi, and a washer and dryer. Guests can also enjoy the private patio with a fire pit and outdoor furniture, as well as the convenience of on-site parking.

Frequently asked questions for the vacation rentals in Peekskill, NY

Destinations nearby

Best pet friendly Peekskill, NY holiday rentals

Among the 85 accommodations in Peekskill, NY, here are the 2 best pet friendly rentals

Jasper Johns' (Former) Home And Studio - Peekskill, NY
8.7Very good 3 reviews
Peekskill, NY
2 2
SG$463/nighttotal: SG$3241 (7 )

Jasper Johns' (Former) Home And Studio

- Stony Point
This charming holiday home is situated in Stony Point, just an hour's drive from New York City, offering a peaceful retreat close to state parks with hiking and biking trails. The property has received very good user ratings, with an excellent location rating and a very good cleanliness rating.
The house features a spacious open plan design, perfect for a family or group of up to four guests. Amenities include a fully equipped kitchen, air conditioning, a garden, a fitness centre, parking, and high-speed Wi-Fi, ensuring a comfortable and enjoyable stay.
Yacht At Dock - On The Waterfront! - Peekskill, NY
9.6Excellent 6 reviews
Peekskill, NY
2 1
SG$230/nighttotal: SG$1610 (7 )

Yacht At Dock - On The Waterfront!

yacht - 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.