
Vacation rentals in Peekskill
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Top-rated vacation rentals in Peekskill
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The Little Cottage in the Woods
The Little Cottage in the Woods Nestled among the trees, and in close proximity to our main house, this studio cottage is newly refurbished, very private and is in a great location to access the Hudson Valley. Hiking trails are within minutes of the cottage or right out the front door. Golf courses are also minutes away. Whether you are in the area on business or just looking to escape for the weekend and enjoy the out doors. It is situated on 9 1/2 hikeable acres, all available to our guests

*Large Pool* Garrison Ultra Modern 5B hottub sauna
Secluded, luxurious 5Br/3.5Bth home an hour from NYC, nested on a 9-acre property with the Appalachian trail running through. Modern-rustic design, floor-to-ceiling windows, custom kitchen, state-of-the-art appliances, balconies. Dip in the heated pool (seasonal) or the hot tub, sauna, dine alfresco from the BBQ and watch the stars. Guests can enjoy morning coffee on the private deck or evening cocoa in front of the wood-burning fireplace or the fire pit, outside, overlooking a private pond.

The Peekskill RiverView House
The Peekskill RiverView House A fully renovated dream house overlooking the historic Peekskill Bay. This 3 bedroom 3.5 bath designer house is a 5 minute walk to the train station, the train is loud, as well as the historic downtown. It’s truly the gateway to the Hudson Valley along with having the walkable access to culture, hiking, biking, culinary, spa, and entertainment activities within City limits. Expansive decks on all 3 floors with spectacular Hudson River views from every room.

The Bluestone - Spacious 2 bedroom w/central air
Come stay with us! You will have the entire first floor to yourself but we will be right upstairs if you should need us! Access to tree lined back yard with fire pit. Close to metro north train to NYC. Minutes to kayaking, hiking, restaurants, cafes & historical sites. Please note: No Kitchen!! Drive, walkway & entrance accessible to full size wheelchair (see photos) but bathroom is not accessible to a wheelchair. Guest must have ability to enter and maneuver the bathroom on thier own.

Special Nest w Private Entrance River View Porches
Front and back porch, river views, spacious living areas, new & fresh kitchen, and *two* bathrooms make this apartment the ultimate landing spot for a fun vaycay! Located on a street filled with intricate historical homes, this first floor apartment offers an accessible and comfortable getaway. A large backyard is shared with other guests, and sweeping river views are only steps away from your front door. Private entrance, plus easy parking and an electric car charger if you need it!

Sweet, stylish cabin in the woods- hiking & more!
Only an hour north of NYC, but a world away! Adorable cabin in the woods offering stylish updated decor and beautiful natural surroundings. Brand new and completely renovated interior, but all the classic charm of the country. Trade in skyscrapers for tall trees in this sweet country escape that is near Fahnestock Park (surrounded by great hiking, skiing, etc) and 15m from the village of Cold Spring. Fully set up w/ wifi, Netflix & more! Quiet, considerate guests only please!

Village Hideaway
1 bedroom apt. steps from Main St...(2 Guest Max.)...Private and quiet, cozy 1 bedroom apartment in the center of the Village, but you’ll feel as if you are a world away, with access to our private Garden and Koi Pond. Just a 7 minute walk to the Metro North train. Within walking distance to everything: Shopping, fine or casual dining, the Hudson River, hiking trails (Breakneck Ridge), even a supermarket, drug store, and post office! Off street parking for one (1) automobile.

Yellow House one bedroom
Recently updated cozy, clean and quiet 1 bedroom apartment with private entrance and parking. Breakfast bar w/ complementary coffee & herbal tea selection. Generous selection of books, movies & music CDs. Well lit living area and kitchen w/ reduced light in bedroom. Just a few minutes walk to Mohegan Lake and Sylvan Glen nature trail. Conveniently located near major highways, metro north train, area restaurants and shopping, popular event venues and outdoor attractions.

Modern+bright forest escape - near village & train
Modern, efficient, and elegant private flexible garden apt. Guesthouse can be used as a studio apartment, or as a private personal retreat space for art/work/rest/meditation. Hiking trails available right out the door, and just a few minutes walk to Cold Spring's vibrant Main Street and Metro North train station to NYC and beyond. Comfortable bed, all modern amenities. Private patio. Native pollinator gardens and forest surround. Solar orientation brings in natural light.

Cozy West Point Hide Away and Cadet’s Get Away
Newly renovated basement space in a very quiet secluded neighborhood with a full kitchen, full size bathroom, Fast WiFi, Smart TV, Separate parking, walking distance to Hudson River, Main Street, Bear Mountain State Park, West Point Military Academy and several adventurous hiking trails. For those who like to shop we are located only 20 minutes to the Woodbury Commons and only a 45 minute drive to NYC. Also Stuart International Airport is only a short drive from here.

Hudson Valley Studio in the Village of Fishkill NY
This spacious studio is in a quiet cul-de-sac and under a half mile walk from the Village of historic Fishkill, NY. Also, only a 10 minute drive to Beacon, NY! It is a private dwelling that includes a full kitchen, 1 new Queen bed, 1 new pull out bed, and a separate room for laundry. Plenty of drawers and closet place caters to up to 4 guests for whichever Hudson Valley activity you're in town for. Come enjoy the atmosphere of this Hudson Valley studio!

Crystal Wave LakeHouse
Make some memories at this renovated, family-friendly Lakefront Oasis! Water activities on your own Peninsula with Lake Frontage on 3 Sides of the Property! Views of the Lake from Almost Every Window! Included is an extra 600 sq ft cottage that has been completely renovated for your enjoyment with a pool table. Utilized as a gaming room & yoga studio! There is a pullout sofa as well for extra guests with a bathroom a few steps away in the main house!
Popular amenities for Peekskill vacation rentals
Other great vacation rentals in Peekskill

SmallRoom in HudsonValleyFarmhouse

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Croton Quarters-Modern Amenities

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

Charming 3 bedroom Cortlandt Manor

Unique comfortable guest suite

Peekskill apartment in the center of downtown

West Point Cottage
Quick stats about vacation rentals in Peekskill
Total rentals
20 properties
Nightly prices starting at
$84 CAD before taxes and fees
Total number of reviews
1.6K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Times Square
- Rockefeller Center
- Bryant Park
- Madison Square Garden
- Empire State Building
- Columbia University
- MetLife Stadium
- Central Park Zoo
- Yankee Stadium
- Mountain Creek Resort
- Fairfield Beach
- Citi Field
- United Nations Headquarters
- Grand Central Terminal
- Rye Beach
- Statue of Liberty
- USTA Billie Jean King National Tennis Center
- Canarsie Beach
- Radio City Music Hall
- The Metropolitan Museum of Art
- Astoria Park
- Bronx Zoo
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area