We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals in Peekskill

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    €556 Average
    |||
    |||
    €0€1,000+
    Suitability
    More filters
    Don't let other travellers get your favourite Peekskill area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 16 Rentals in Peekskill
    Sort by:
    Default
    The following rentals are within 15 kilometers of Peekskill.
    Castle By The Lake1 / 15
    (3)Excellent
    Putnam Valley, NY
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
    other travellers have booked this property
    Certificate of Excellence
    Check in Check out
    Show Prices
    Payment Protection
    Beautiful 4 br in historic Cold Spring!1 / 24
    (4)Excellent
    Cold Spring, NY
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Garrison, NY
    3 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Putnam Valley, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Terrace
    • DVD Player
    • Secure Parking
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lakefront paradise has waterfront views that will leave you breathless. It is rated five star by Baron Realty and Fulline Home Research. The property is located one hour north of Manhattan off the Taconic Parkway or 15 min. east of the Garrison, New York Metro North train station on the...
    View all property information
    Location Information
    Putnam Valley, New York 10579
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Fort Montgomery, NY
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly created spacious 1 Bedroom apartment in historic Fort Montgomery NY. Minutes to West Point, Bear Mountain and many other historic sites. Nestled in the heart of the Hudson highlands we are situated amongst some of the Hudson valley's most scenic and historic sites in NY State. Access is easy...
    View all property information
    Location Information
    Fort Montgomery, New York 10922
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    Pomona, NY
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Grill
    • Washer
    • Hot Tub
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to 'THE HILLTOP' NOT READY FOR SUMMER'S END?? EXTEND YOUR SUMMER SEASON AT 'THE HILLTOP' POOL OPEN TIL END OF SEPT W/ WARM WATER!!!! BOOK YOUR WEEKEND/WEEKLY SEPT STAY NOW Rockland County 6000 sq ft Country Estate with Modern Flair on 1 acre of secluded grounds. This...
    View all property information
    Location Information
    Pomona, New York 10970
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    Make Enquiry
    Cold Spring, NY
    5 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come relax and refresh and recharge in our little slice of heaven just an hour and a half north of the city, outside the bucolic town of Cold Spring on the Hudson. We built it in 1995 on five acres of woodland, nestling the house in the hillside with the adjacent pool in a woodland glade, and a...
    View all property information
    Location Information
    Cold Spring, New York 10516
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 9
    Make Enquiry
    Westchester Hudson Valley Estate - Private, less than 1 hour from NYC1 / 11
    (2)Excellent
    Croton on Hudson
    8 Bedrooms, 7 Bathrooms, Sleeps 24 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Washer
    • Patio
    • DVD Player
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 November 2017
    This site was truly amazing. The accommodations were beyond expectations. The home has a very friendly warm feeling. There were seventeen of us and each party had their own...
    Reviewed 28 November 2017
    We were looking for a house that would be large enough for our family and we booked Greta's place. The house was fantastic! It had 8 unique bedrooms each with period furniture...
    See all reviews
    About this property
    Secluded and private on over 100 protected acres, this historically significant 1800's estate boasts a good amount of extras. Historic, yet updated and upgraded with modern touches. Private tennis court, hiking trails, fishing, golf course (4 miles away), kayaking the Hudson River,...
    View all property information
    Location Information
    Croton on Hudson, Westchester County 10520
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 24
    Make Enquiry
    Garrison, NY
    5 Bedrooms, 3 Bathrooms, Sleeps 15 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • DVD Player
    • Sauna
    • Washer
    • Hot Tub
    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Do you have a special Birthday ? Anniversary? How about a work retreat ? or do you want a break from the concrete jungle ? This charming 1910 farmhouse is perfect for resting, relaxation, restoring. It is fantastic for preparing meals as a group and having a decadent dinners with close friends...
    View all property information
    Location Information
    Garrison, New York 10524
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 15
    Make Enquiry
    Fort Montgomery, NY
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Secure Parking
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Fort Montgomery, New York 10922
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    Save time - get the best Peekskill rentals sent straight to your email!
    Get the List
    Croton on Hudson
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Mountain Views
    • Grill
    • Balcony
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The apartment is attached to the main house with a separate,private entrance. The apartment exits onto a patio next to the pool. It has a living room, bathroom and kitchen. Fully furnished. It is located on 3 acres of lawn and woodland. It is quiet. We are 48 minutes by train from mid...
    View all property information
    Location Information
    Croton on Hudson, Westchester County 10520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Our Rockbound Highland Home * 2 Blocks to West Point * 1/2 Block to Main St1 / 12
    (3)Excellent
    West Point, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Parking
    • Washer
    • Grill
    • Mountain Views
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 July 2018
    Anytime we can stay here while visiting USMA we most certainly will do so. The accommodations were fantastic as well as the location. Heather and Dan are wonderful hosts and...
    Reviewed 25 June 2018
    We were lucky enough to get this place as a short term rental. The owners are amazing! The place can’t be beat! Beds are comfy with high end linens and pillows. Spacious with...
    See all reviews
    About this property
    This charming historic home is located only 2 blocks from Thayer Gate at the United States Military Academy at West Point, a half block from Main Street shops and restaurants, and 3 blocks from the West Point Visitors Center and Museum. We are a Vivint Smart Home, offering keyless access and 24/7...
    View all property information
    Location Information
    West Point, New York 10928
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 11
    Make Enquiry
    Highland Falls, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Washer
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome! This gorgeous, JUST built home in Highland Falls is the perfect luxurious getaway only minutes from all the excitement the city has to offer. This house is a new built, so literally everything from floor to ceiling is brand new including top of the line appliances. **While this is a new...
    View all property information
    Location Information
    Highland Falls, New York 10928
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 12
    Make Enquiry
    Garrison, NY
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Easy access to train, hiking, recreation, river Charming 2 bedroom cottage Easy access to New York City as well as recreational areas in the region. Beautiful environs, lots of trees, birds, mostly quiet. Home bright with daylight Air conditioned 10 minutes from Cold Spring 20 minutes to Beacon
    View all property information
    Location Information
    Garrison, New York 10524
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Cortlandt Manor
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Porch
    • Grill
    • Mountain Views
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is an independent room with separate access. The room is fully furnished with a queen bed, breakfast table, couch, Cable TV and internet. The room also has a separate kitchen and a shared laundry. The guests are allowed to cook with an electric /induction stove.Two miles from Annesville creek...
    View all property information
    Location Information
    Cortlandt Manor, Cortlandt 10567
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Garrison, NY
    5 Bedrooms, 3 Bathrooms, Sleeps 15 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The perfect weekend getaway within one hour of NYC. Easily accessible by Metro North. Within walking distance of train. We cater to corporate retreats, birthdays, bachelorette, production location + more. Many amenities: pool, full gym, sauna, hot tub, steam room relaxation guaranteed ! Welcome...
    View all property information
    Location Information
    Garrison, New York 10524
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 15
    Make Enquiry
    List your property
    Owner log in