
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.

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.

Stylish Private Studio 1 block from Main St Beacon
Stylish, private garden level bedroom & bath w/ self check-in private entrance. Art/antiques/vintage bar-cart/mini-fridge/ microwave/43in 4KTV w Netflix/ black-out curtains/outdoor seating area. 1 block from Main St, 3 min free shuttle/20 min walk from Metro-North station. Close to DIABeacon & hiking trails. NOTE: -Ceilings are a bit low so if you are very tall, please contact me before booking. -To add pet,click "guests" dropdown, scroll to bottom&select "pet" to pay fee. $45 xtra for 2nd pet

Ranch in the Woods | A Peaceful Designer Retreat
Welcome to @ranch_inthewoods No cleaning fee STR permit #34035 This newly built ranch-style home with thoughtfully designed wabi-sabi interiors sits in the woods of the Warwick Valley. It's located a short drive away from several lakes, hiking trails, breweries, and dining experiences. It features forest/creek views, designer furniture, modern appliances (dishwasher, washer/dryer, gas cooktop), smart 4k TV, gym & yoga studio, gas firepit, and ample deck with an outdoor kitchen & dining area.

Secluded Hilltop Cabin near Beacon & Cold Spring
3 private acres atop small mountain. Feels like you're way upstate - check out the reviews! Hi-speed WiFi. Next to forest preserve and hiking trails. Furnished deck w grill overlooks Mt. Beacon sunsets. Loft w/queen and twin mattresses + pull out couch & twin-size mattress day bed on the porch. Perfect for 2, comfortable for 3, but 4 is probably max comfort since it's a small space. Please note that the road heading up there is steep. A car with AWD is ideal but a sedan will make it up too!

Super Spacious Clean Comfy Private Secure
Super Spacious and private for 1 or 2 guests with 2 extra comfy queen sized beds Safe and secure Single traveler discount (ask) Dedicated workspace/Wifi Private parking Private entrance 42 inch tv Luxurious bathroom/ heated Jacuzzi bathtub/seated shower Coffee/tea/snacks Perfectly located for- Stewart Airport Storm King Art Center USMA West Point Woodbury Common DIA Beacon Local hiking Wineries Popular wedding venues -No cooking allowed. Inquire about extra guests. Relax. Enjoy. Book now.

Boulder Tree House
Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

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!

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.

Charming Efficiency
Newly refurbished efficiency apartment. Full kitchen, new appliances. Comfy space with queen bed and shower in bathroom. Short stroll to coffee bar & all of Cornwall! 3 miles to West Point. Ten minute drive to Storm King, Dia in Beacon, restaurants on the Hudson River. LOTS of hiking options, wine trails and exploring the Hudson Valley. Woodbury Commons is 10 miles for those who prefer shopping! Happy to help with dinner reservations & help to make your stay memorable! Pet friendly.

2-Bedroom in COH, near Newburgh & West Point
Two-bedroom apartment located right in the village of Cornwall-on-Hudson. Right next to the fantastic Italian Restaurante Peppitini and right across the street from the historic bandstand, if you're here on a Tuesday night in the summer, you'll likely be able to have a drink and catch a concert from the porch! Conveniently located close to West Point, Storm King Art Center, Newburgh, great hiking, and even Hudson River kayaking! The two bedrooms are roomy and each has a queen bed.

Historic 1 bedroom home in Cold Spring, NY
This lovingly restored home, built in 1826,is located within the hamlet of Nelsonville within walking distance of the village of Cold Spring. This home has its own entrance and private courtyard and is attached to the owners main residence. Space is curated with antiques and is intended for a couple. This is cozy any time of the year. This home is near trailheads of spectacular hikes in the Hudson Highlands and at the base of Bull Hill.

Ela - a 1 Bed Escape, Washer/Dryer in Unit
Kick back and relax in this calm, stylish space. Located on the second floor of a historic Newburgh building, this apartment features scenic views from oversized windows, in-unit laundry, LED TV & Fios WiFi, and designer furnishings. Queen bed with Casper mattress. Two flights of stairs required. The neighborhood is quiet, with tree lined streets and historic mansions nearby, just 2 blocks always from the Hudson River waterfront.
Popular amenities for New Windsor vacation rentals
Other great vacation rentals in New Windsor

Rustic Ranch w/ Fire Pit, Trails & Grazing Horses

River Views • Spa Baths • Hot Tub | Artisan Stays

Accord River House

Arkadia House Mid-century retreat with pool & view

Cornwall on Hudson Private Apartment

*Charming Home & Convenient Location w/ Parking*~

Expansive Views Whole Private House

Mountain Top Retreat
When is the best time to visit New Windsor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $164 CAD | $178 CAD | $202 CAD | $204 CAD | $205 CAD | $206 CAD | $223 CAD | $225 CAD | $225 CAD | $225 CAD | $225 CAD | $219 CAD |
| Avg. temp | -4 °C | -2 °C | 2 °C | 9 °C | 14 °C | 19 °C | 22 °C | 21 °C | 17 °C | 10 °C | 5 °C | -1 °C |
Frequently Asked Questions
Are there family-friendly vacation rentals in New Windsor?
New Windsor has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
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 $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget 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.
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.
Do house rentals in New Windsor have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in New Windsor. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in New Windsor have a kitchen?
Absolutely! We offer over 10 apartment rentals with a kitchen in New Windsor. Enjoy a tailored experience with all the comforts you desire.
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.
Do house rentals in New Windsor have free parking?
Absolutely! We offer over 10 house rentals with free parking in New Windsor. Enjoy a tailored experience with all the comforts you desire.
Quick stats about vacation rentals in New Windsor

Total vacation rentals
Explore 40 vacation rentals in New Windsor

Nightly prices starting at
New Windsor vacation rentals start at $82 CAD per night before taxes and fees

Verified guest reviews
Over 2,840 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
40 of New Windsor vacation 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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