Holiday houses in New Windsor

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in New Windsor

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

0 of 0 items showing

1 of 3 pages

Guest favourite

Guest suite in Montgomery

4.95 out of 5 average rating, 418 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

29 Jan – 5 Feb

$1,512 AUD total

Guest favourite

Apartment in Newburgh

4.95 out of 5 average rating, 201 reviews

Grant - A Tranquil One Bedroom Steps from River

The Grant - an elegant one bedroom in a historic Newburgh building steps from the Hudson. Tastefully presented by Hendley & Co - a local design boutique - this sun-drenched unit features 11 foot ceilings, oversized windows, and murals by artist Megan Galante. High end furnishings throughout provide a relaxing stay or a peaceful work-from-home environment. Ferry to Beacon within walking distance. Amenities include a large backyard/porch, Fios 300Mbps WiFi, LG washer/dryer, dishwasher & more.

21 – 28 Sept

$1,904 AUD total

Guest favourite

Apartment in New Paltz

4.96 out of 5 average rating, 344 reviews

Modena Mad House

Our apartment is 6 miles from downtown New Paltz on a quiet and private setting only 1.5 hours from New York City, in the heart of Hudson Valley's Wine Country and apple/peach orchards. 1 bedroom apartment with separate kitchen living room and front porch. Fridge is stocked with eggs, bread, cheese, coffee, wine. We have a large HD screen TV and Roku, but no local cable. 7 miles from Mohonk Preserve and 10 miles from Gunks climbing area, and great Cross-country skiing. Self check-in

10 – 17 Jan

$1,399 AUD total

Guest favourite

Cottage in Newburgh

4.88 out of 5 average rating, 185 reviews

Cozy Lake Cottage

Cozy cottage in residential lake community, adjacent to historic fine dining restaurant. There is an approximate 150 yard walk down to the lake to enjoy the spectacular sunsets . Centrally located in the Hudson Valley near everything there is to experience. Located in our area Many Local Wineries ( Angry Orchard) Orange County Choppers Cafe Woodbury Commons Outlet Mall Historic Newburgh and Waterfront Culinary Institute of America US Military Academy New Paltz and Mohonk Mountain House

29 May – 5 June

$1,544 AUD total

Guest favourite

Guest suite in Marlboro

4.96 out of 5 average rating, 391 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.

26 June – 3 July

$1,353 AUD total

Guest favourite

Apartment in Marlboro

4.97 out of 5 average rating, 307 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.

2 – 9 Dec

$1,451 AUD total

Superhost

Apartment in Newburgh

4.84 out of 5 average rating, 113 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!

21 – 28 Sept

$1,720 AUD total

Guest favourite

Apartment in Newburgh

4.93 out of 5 average rating, 379 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.

21 – 28 Dec

$1,821 AUD total

Guest favourite

Apartment in Newburgh

4.93 out of 5 average rating, 212 reviews

Eco MidCentury Modern Retreat

Fab Mid-Century Eco friendly apartment is all you need for a relaxing Hudson Valley Retreat! Close proximity to all Hiking areas , Storm King, West Point, Beacon DIA , Newburgh Assembly (8 min) and centrally located to all Bethel facilities Wallkill,Patterson and Warwick. This cozy two bedroom downstairs walkout apartment is tucked away and sits amongst the trees with large windows to enjoy nature. Also, features a large private patio , table, chimnea fireplace and BBQ.

23 – 30 Sept

$1,605 AUD total

Guest favourite

Tiny home in Newburgh

4.88 out of 5 average rating, 521 reviews

Cabin in the heart of the Hudson Valley, Cabin 2

Our little cabin is perfect for one or two guests for short stays while visiting local family, touring the areas wineries or nature trails, or for a clean, quiet over night stop while traveling long distances. Explore the Shawangunk Wine Trail, hike Minnewaska, sip cider at Angry Orchard, visit The Walkway Over the Hudson, or sample and shop the areas diverse farm stands and breweries. There is so much to see and do in the Hudson Valley and our cabin is close to it all!

16 – 23 July

$1,548 AUD total

Guest favourite

Guest suite in Newburgh

4.93 out of 5 average rating, 445 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.

23 – 30 Mar

$1,558 AUD total

Guest favourite

Guest suite in Newburgh

4.92 out of 5 average rating, 165 reviews

Hudson River Views-romantic getaway close to NYC

Cozy suite with fireplace and private deck views of the majestic Hudson River nestled in a quiet safe neighborhood away from the city of Newburgh yet close by. This suite has a full kitchenette and a separate living space with couch, smart TV, queen bed and table. It has its own deck accessible by a sliding glass door where you can enjoy sunrises and soak in the peaceful views. Ask us about our car for rent thru the Turo app.

1 – 8 Dec

$1,454 AUD total

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for New Windsor holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Stay near New Windsor's top sights

Destinta Theaters5 locals recommend

Nature's Pantry25 locals recommend

Plum Point Park8 locals recommend

Cilantro Restaurant And Bar4 locals recommend

United States Postal Service3 locals recommend

Kowawese Unique Area3 locals recommend

Other great holiday rentals in New Windsor

Guest favourite

Tiny home in Marlboro

4.96 out of 5 average rating, 280 reviews

Orchard Views from a Light-Filled Tiny Home with a Fire Pit

20 – 27 Aug

$1,866 AUD total

Guest favourite

Home in Wappingers Falls

4.98 out of 5 average rating, 102 reviews

Tranquil Tree-House on the beautiful Hudson River

4 – 9 Sept

$1,513 AUD total

Guest favourite

Apartment in Newburgh

4.85 out of 5 average rating, 140 reviews

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

26 June – 3 July

$1,492 AUD total

Guest favourite

Apartment in Cold Spring

4.95 out of 5 average rating, 519 reviews

Beautiful loft space

27 Mar – 3 Apr

$2,212 AUD total

Guest favourite

Guest suite in Chester

4.95 out of 5 average rating, 229 reviews

Adorable Guest Apartment in Victorian Mansion

26 Jan – 2 Feb

$1,265 AUD total

Superhost

Home in New Windsor

5.0 out of 5 average rating, 3 reviews

1 Bedroom Sleeps 5 West Point

27 Sept – 4 Oct

$1,267 AUD total

Guest favourite

Apartment in Newburgh

4.9 out of 5 average rating, 79 reviews

Bright and Stylish 1-bedroom Apartment

17 – 24 Apr

$1,638 AUD total

Superhost

Home in New Windsor

*Charming Home & Convenient Location w/ Parking*~

7 – 14 July

$2,126 AUD total

Show all

Quick stats about holiday rentals in New Windsor

Total rentals	30 properties
Rentals with dedicated workspaces	20 properties have a dedicated workspace
Pet-friendly rentals	10 properties allow pets
Family-friendly rentals	10 properties are a good fit for families
Total number of reviews	2.1K reviews
Nightly prices starting at	$62 AUD before taxes and fees

Holiday houses in New Windsor

Top-rated holiday rentals in New Windsor

Guest suite in Montgomery

Apartment in Newburgh

Apartment in New Paltz

Cottage in Newburgh

Guest suite in Marlboro

Apartment in Marlboro

Apartment in Newburgh

Apartment in Newburgh

Apartment in Newburgh

Tiny home in Newburgh

Guest suite in Newburgh

Guest suite in Newburgh

Holiday rentals for every style

Apartments

Hotels

Unique stays

Popular amenities for New Windsor holiday rentals

Stay near New Windsor's top sights

Other great holiday rentals in New Windsor

Tiny home in Marlboro

Home in Wappingers Falls

Apartment in Newburgh

Apartment in Cold Spring

Guest suite in Chester

Home in New Windsor

Apartment in Newburgh

Home in New Windsor

Quick stats about holiday rentals in New Windsor

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Destinations to explore