Holiday rentals in New Windsor

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Top-rated holiday rentals in New Windsor

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A bright bedroom features a spacious bed with crisp linens and a patterned rug. Two windows allow natural light to fill the room, complemented by neutral wall tones. A bedside table holds decorative items, and a potted plant adds a touch of greenery.
Flat in Cornwall-on-Hudson
4.93 out of 5 average rating, 135 reviews

Quaint Apartment in Cornwall on Hudson

Looking for a weekend getaway? Come experience this centrally-located apartment in the quaint village of Cornwall-on-Hudson. Step outside to find river views, enjoy miles of hiking trails, Hudson River picnics and kayaking that start right up the road. Just minutes to West Point, the Storm King Art Center, Mount Beacon and Woodbury Commons and still in walking distance to shops, restaurants, and parks. We’re excited to make this your favorite place to stay while visiting the Hudson Valley area.

Top guest favourite
A tiny house with large windows is nestled among the trees, offering a secluded retreat. A wooden deck with stairs leads to the entrance. An outdoor dining space with an umbrella and a propane grill is visible alongside a gravel area, complemented by a playful dog on the lawn.
Tiny home in Wallkill
4.99 out of 5 average rating, 328 reviews

Get Away to "Hygge" Tiny House on 75 Private Acres

Escape to 75 acres of secluded, private land and lounge in this "hyggelig" tiny house. The house has everything you need, from heat and A/c, strong wifi, TV with streaming (sign in to Netflix, HBO, etc), full working kitchen (gas stove, oven, microwave), shower and bathroom. This tiny house has an incredible amount of light coming in from the very large windows throughout. Outdoor amenities include wood patio, propane bbq grill, dining table/chairs, fire pit. Lawn games available on request.

Top guest favourite
The sleeping area features two spacious beds, each with coordinating linens in calming green tones. Warm light is provided by two bedside lamps, enhancing a cozy ambiance. A decorative ottoman and a circular rug add texture and comfort to the inviting space.
Guest suite in New Windsor
4.96 out of 5 average rating, 257 reviews

Artistic Loft Private Home baked goodies

Features - 2 Super comfy queen sized beds. 2 Twin - Huge bathroom - Tub - Seated shower -Coffee/Tea/Snacks/Morning Muffins - Kitchenette - Private driveway. Parking at door. - Dedicated work desk. Wifi -Single traveler discount - Extra guest fee over 2 guests - 5 min SKAC -12 min USMA -10 min Woodbury Common -15 min Newburgh Riverfront Restaurants -25 min Beacon -35 min Bethel -Must be 25 years or older to book. No parties or gatherings. -6 guest maximum (inquire) -No 3rd party bookings

Superhost
A cozy sleeping area features a queen-size bed dressed in a red and black plaid comforter. Two lamps are positioned on either side, providing soft lighting. A small nightstand holds decorative items, while a trunk for storage is located at the foot of the bed.
Loft in Mountainville
4.84 out of 5 average rating, 599 reviews

Country Getaway - Close to Hiking & Storm King

Enjoy the countryside minutes away from downtown restaurants, bars and Main Street, in our private, cozy loft studio! Located on 1.5 acres, this clean and comfortable apartment includes a kitchenette with bar-style table, living room and two flat screen Roku TV’s with Netflix, Hulu as well as an electric fireplace, outdoor patio and fire pit. Guests have two parking spaces, a private first-floor entrance, private full bathroom, outdoor dining area, BBQ and fire pit! Pool available seasonably.

Guest favourite
A spacious studio apartment features a comfy bed with multiple pillows and a cozy sofa. A ceiling fan provides comfort, and a wall-mounted TV is visible. A wooden table displays brochures, while natural light filters through the nearby windows, creating a bright and airy atmosphere.
Flat in Beacon
4.99 out of 5 average rating, 174 reviews

2BlocksToMainSt/Roundhouse Under Mt Beacon Pvt Apt

A cozy, clean, large studio apartment within a two minute walk to Mt. Beacon and Main St. Enjoy your stay with a fully equipped kitchen (coffee, tea, creamer, sugar, etc.), a comfy queen bed with lots of pillows, a full bathroom with shampoo, conditioner, body wash and extras. You will have off-street parking and a beautiful outdoor patio all to yourself. The apartment has WiFi, a Smart T.V. and lots of lighting but also room darkening shades to sleep in. Pickleball courts 2 blocks away.

Superhost
A light-filled space features a well-equipped kitchen with modern appliances and a minimalist design. The wooden staircase, adorned with potted plants, leads to a cozy upper area. Natural light streams in through the window, illuminating the warm wooden flooring and vibrant area rug.
Flat in Newburgh
4.84 out of 5 average rating, 340 reviews

Unwind in a Bespoke Downtown Studio W Laundry

A bright & creative studio apartment welcomes you! Totally renovated by us for our family, and now available to you. Pros: ♥Automated check in (no waiting!) ♥ Comfy queen sized murphy bed with a real mattress ♥ Open space hang out, work, play, etc ♥Walkable neighborhood ♥Custom design with unique features (hand made tile, Murphy bed, commissioned mural) Cons: ☆Second floor apartment (one flight of stairs) ☆Rooftop not available in late fall/winter ☆ Studio apartment Welcome home!

Guest favourite
A bright sleeping area features a spacious bed with white linens, complemented by two decorative pillows. A small side table with a lamp is positioned beside the bed. Light wood flooring and a window with dark curtains add warmth to the space. A chair and artwork are visible along the wall.
Flat in Beacon
4.93 out of 5 average rating, 144 reviews

Cozy, Small Studio with Backyard & great A/C

Cozy, small studio on quiet block. Near Main Street, Roundhouse, hiking, restaurants. Fully private space & entrance, shared backyard, new A/C, wifi. Walk everywhere. Queen-sized bed. BEFORE YOU BOOK - 200 year old house - hosts live upstairs and there is another guest apartment. You WILL NOTICE sounds from others. QUIET HOURS from 10 PM to 8 AM. As a courtesy to others, please keep conversations quiet after 10 PM. We only book guests with favorable Airbnb reviews. NO SMOKING please.

Top guest favourite
A spacious bedroom features a large queen bed with a contrasting striped blanket. Nightstands are positioned on either side, and a lamp provides soft lighting. Two windows with light-filtering curtains allow natural light to fill the room, complemented by a beige carpet.
Guest suite in Marlboro Township
4.96 out of 5 average rating, 503 reviews

Spacious & Private Hudson Valley Getaway

Welcome to Marlboro! This private space in our home features a private entrance, private bathroom with a nice standing shower, eating area (not a kitchen) with tea kettle and coffee machine, toaster, microwave and refrigerator with freezer. There is a table and chairs, love seat couch that transforms into a small cot, queen bed, walk in closet and 55 inch smart TV with a full motion TV stand. We are permitted to operate in the town of Marlboro and a yearly fire inspection is conducted.

Top guest favourite
A rustic bench is positioned along a wooden fence, offering a vantage point of rolling hills adorned with autumn foliage. The scene captures a bright, open sky dotted with fluffy clouds, enhancing the natural beauty of the surrounding landscape.
Flat in Marlboro Township
4.98 out of 5 average rating, 416 reviews

Cliff Top at Turtle Rock

Cliff Top retreat with a one hundred mile view of the Shawangunk's and the Catskill Mountains, surrounded by thousands of acres of ancient forest. Conveniently located in the Hudson Valley Wine and Orchard country. Twenty minutes from Beacon and New Paltz. Furnished with mid-century and 18th century period furniture and art work, yet with all the modern conveniences. Uber and Lift an easy five minutes away. The ancient forest contains many Stone Age rock shelters and calendar sites.

Superhost
A bedroom features a spacious bed with neutral-toned bedding and decorative pillows. A small bedside table holds a clock, while a light fixture hangs above. The room is brightened by natural light streaming through a window with blinds, contrasting with the warm wooden floor and white walls.
Flat in Newburgh
4.93 out of 5 average rating, 480 reviews

Riverview Rowhouse, a vintage modern home

Stylishly renovated 1890 Rowhouse in Newburgh's up-and-coming Washington Heights District. Enjoy your morning coffee with views of the Hudson River and Mountains. Just 75 minutes from NYC, this home is a short drive to the Newburgh Waterfront and Liberty Street's hip new shops and restaurants such as Ms. Fairfax, The Flour Shop, Liberty Street Bistro, Mama Roux, The Newburgh Brewery, and more. Close proximity to the Beacon Ferry and a short drive to the Beacon train station.

Top guest favourite
A sunlit open space features a light-colored wooden floor and white walls. Two large windows invite natural light, while a patterned area rug adds warmth. A small table and chairs are arranged nearby, creating a versatile area for dining or work.
Guest house in Cold Spring
4.99 out of 5 average rating, 194 reviews

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.

Top guest favourite
A staircase is depicted, featuring dark wooden steps and a polished handrail. Natural light enters through a nearby window, illuminating the neutral-colored walls. The staircase leads upward, accentuating the vintage charm of the home.
Guest suite in Newburgh
4.93 out of 5 average rating, 612 reviews

Glenbrook Country Villa

1856 high gothic revival brick country villa designed by architect Frederick C. Withers (Jefferson Market Library) in the hamlet of Balmville. Within the house is a cozy one bedroom second floor suite through a private side entrance and up a flight of stairs. Freshly updated with a mix of antique and contemporary furnishings against a backdrop of safe but stylish Farrow & Ball paint colors. Relax, enjoy complementary coffee and tea -- just make yourself at home.

Popular amenities for New Windsor holiday rentals

When is the best time to visit New Windsor?

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Frequently Asked Questions

  • Do apartment rentals in New Windsor have free parking?

    Absolutely! We offer over 10 apartment rentals with free parking in New Windsor. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in New Windsor?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with a kitchen, over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • How much does it cost to stay in apartment rentals in New Windsor?

    Experience the best of New Windsor with our apartment rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do apartment rentals in New Windsor have wifi?

    Absolutely! We offer over 20 apartment rentals with wifi in New Windsor. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in New Windsor?

    New Windsor has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do apartment rentals in New Windsor have air conditioning?

    Absolutely! We offer over 10 apartment rentals with air conditioning in New Windsor. Enjoy a tailored experience with all the comforts you desire.

  • Are there apartment rentals with a dedicated workspace in New Windsor?

    Yes! Work meets play with ease at over 10 apartment rentals in New Windsor featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in New Windsor?

    Four-legged friends are welcome in New Windsor. Choose from more than 10 vacation rentals for guests traveling with pets.

Quick stats about holiday rentals in New Windsor

  • Total holiday rentals

    Explore 40 holiday rentals in New Windsor

  • Nightly prices starting at

    New Windsor holiday rentals start at £38 per night before taxes and fees

  • Verified guest reviews

    Over 2,670 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    40 of New Windsor holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across New Windsor rentals

  • 4.8 Average rating

    New Windsor stays are highly rated by guests – averaging 4.8 out of 5!

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