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Vacation rentals in New Windsor

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Top-rated vacation rentals in New Windsor

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

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Guest suite in Montgomery

4.95 out of 5 average rating, 459 reviews

Garden View Guest Cottage

Located under 15 min. to Stewart Airport...1 mile to City Winery , nearby Angry Orchards , 1/2 hour to West Point Charming cottage setting located in the village of Montgomery, NY, Come for the day or stay for a few to take in all this historic area has to offer. Walk to some of the best restaurants in Orange County or simply read a book in the gardens... Truly a great value since it's a true "apartment " like setting..not just a room, with all the conveniences and sleeps up to 6 people

Rental unit in Newburgh

4.86 out of 5 average rating, 182 reviews

Riversong on Hudson - Private Full 2nd Floor

This 2nd floor sanctuary is not just a place to stay. Aside from the trains frequently passing nearby, Riversong is a pocket of peace, a window to breathtaking views, and a gateway to a historic city. In this light-filled abode, classic charm meets contemporary comfort. The living area, with a convenient, plush futon, offers space to relax or host an additional guest. Picture windows frame the outdoors, inviting you to gaze on the tranquil river and verdant tapestry of the landscape beyond.

Guest suite in Chester

4.96 out of 5 average rating, 285 reviews

Adorable Guest Apartment in Victorian Mansion

This lovely 3rd floor private apartment is in an 1883 Victorian Mansion in Blooming Grove, NY for 1 - 6 people. It is beautifully furnished, and has luxurious beds, so let us know if you need one, two or three bedrooms! The apartment has a private entrance, a claw foot tub, a French door shower, and a kitchenette with sunny breakfast nook. It is freshly renovated and spacious. You will have to take 2 staircases. Our land has a nice view of a field of wildflowers, and our neighbor has cows.

Home in Newburgh

5 out of 5 average rating, 120 reviews

Hillcrest Glasshouse - a minimalist modern retreat

The Hillcrest Glasshouse is a fully renovated peaceful retreat with modern carefully selected furniture featuring a breathtaking view over the Hudson River with a fully equipped kitchen, outdoor fire pit, outdoor grill, indoor fireplace, AC, Sonos sound system, Netflix, Amazon Prime, Cable and excellent Wifi to satisfy all leisure and home office activities. This beautiful getaway is only 70 miles away from midtown NYC and close to many of the Hudson Valley's most visited destinations.

Rental unit in Marlboro

4.98 out of 5 average rating, 345 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.

Rental unit in Newburgh

4.85 out of 5 average rating, 162 reviews

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!

Rental unit in Newburgh

4.93 out of 5 average rating, 430 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.

Guesthouse in Cold Spring

4.98 out of 5 average rating, 132 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 sunlight.

Guest suite in Newburgh

4.93 out of 5 average rating, 520 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.

Home in Wappingers Falls

4.93 out of 5 average rating, 176 reviews

Tranquil Tree-House on the beautiful Hudson River

Take it easy at this unique and tranquil getaway. Be our guest at our beautiful home located on the widest part of the Hudson River. Enjoy a private room with a queen size bed and a large screen smart tv. The full bathroom is located across the hallway. Enjoy a warm fire in the sitting area. There is a work area and a high table to enjoy some tea/coffee or wine with dinner while enjoying the view of the Hudson through the large windows and sliding door.

Rental unit in Newburgh

4.9 out of 5 average rating, 107 reviews

Ethereal Apartment with parking on site

Kick back and relax in this stylish open floor plan. Located on the top floor of a historic Newburgh building, this apartment features smart TV & High speed Fios WiFi, an in-unit laundry, designer furnishings, and a separate office space for WFH. Suitable for 2-4 guests, there is one King and one Queen sized bed. Both are hybrid memory foam mattresses with natural cotton bedding for ultimate comfort and tranquility. Two flights of stairs are required.

Loft in Cornwall

4.86 out of 5 average rating, 461 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 flat screen Roku TV with Netflix, Hulu as well as an electric fireplace, outdoor patio and fire pit. Guests have their own parking space, a private first-floor entrance, full bathroom, patio, BBQ and fire pit!

Vacation rentals for every style

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Popular amenities for New Windsor vacation rentals

Free parking on premises

Air conditioning

Stay near New Windsor's top sights

Newburgh Brewing Company87 locals recommend

Hudson Taco78 locals recommend

Billy Joe's Ribworks69 locals recommend

Washington's Headquarters State Historic Site54 locals recommend

Liberty Street Bistro46 locals recommend

Ms. Fairfax45 locals recommend

Other great vacation rentals in New Windsor

Guest suite in Cornwall

4.96 out of 5 average rating, 77 reviews

Studio in Cornwall

Rental unit in Philipstown

4.9 out of 5 average rating, 216 reviews

Foxglove Farm

Home in Newburgh

4.86 out of 5 average rating, 22 reviews

Margaret's Heart

Loft in Mountainville

4.97 out of 5 average rating, 112 reviews

Lovely, Quiet and Very Private! Entire Loft!

Rental unit in Newburgh

4.86 out of 5 average rating, 149 reviews

#1, Historic Studio, Newburgh, Beacon, West Point

Cottage in Newburgh

4.86 out of 5 average rating, 207 reviews

Cozy Lake Cottage

Tiny home in Wallkill

4.99 out of 5 average rating, 250 reviews

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

Rental unit in Cornwall-on-Hudson

4.98 out of 5 average rating, 52 reviews

Cornwall on Hudson Private Apartment

Quick stats about vacation rentals in New Windsor

Total rentals
40 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
2.4K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace

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 $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in New Windsor have wifi?
Absolutely! We offer over 10 house rentals with wifi in New Windsor. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in New Windsor?
New Windsor has more than 10 family-friendly stays. 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 20 apartment rentals with air conditioning in New Windsor. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in New Windsor?
Yes! Work meets play with ease at over 20 vacation 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.

Destinations to explore