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Featured Apartments in New Windsor and around

The Wine House, Sitting atop of Warwick's brand new Wine Bar
10.0 out of 10, Exceptional, (4)
"The apartment above the Wine Bar is lovely. It was a cozy space with a very comfortable bed. It was very clean and nicely decorated. It is a few steps away from the main shopping/dining district in Warwick. The gift cards to a local cafe and restaurant which were given by the host were utilized and greatly appreciated! The host was courteous and attentive. Highly recommend! "
The price is €231
includes taxes & fees
30 Sept - 1 Oct
The Wine House, Sitting atop of Warwick's brand new Wine Bar
Walk to EVERYTHING West Point-2mins to Academy! Mountain Views/private parking
9.2 out of 10, Wonderful, (17)
"This apartment is in an old building in Highland Falls, on the third floor you reach via a narrow, steep staircase. The apartment itself, although as old as the building, is furnished with contemporary furniture, a modern kitchen and bathroom, new sheets and pillows, and is extremely clean. We enjoyed our stay there."
Walk to EVERYTHING West Point-2mins to Academy! Mountain Views/private parking
Private Guest Suite on 8 Acres,Mountain Views, Walk to Rail Trail, 2min to Town
2.0 star property
8.8 out of 10, Excellent, (3)
"The place was great! The hostess was so sweet and on a scale of 1 to 10 the stay was an awesome 10"
Private Guest Suite on 8 Acres,Mountain Views, Walk to Rail Trail, 2min to Town
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
10.0 out of 10, Exceptional, (43)
"The house was neat, clean and exactly as advertised. Two outdoor firepits and right on the water. Was great!"
The price is €232
includes taxes & fees
27 Oct - 28 Oct
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Sweet spot studio on village outskirts
10.0 out of 10, Exceptional, (20)
"Our second stay in 2 months. The apartment is very clean, very close to town and the hosts are friendly and responsive. I can’t recommend enough!"
Sweet spot studio on village outskirts
Modern penthouse suite in a restored grain tower with private roof deck.
9.8 out of 10, Exceptional, (9)
"We really enjoyed our stay at the grain tower. The apartment was super unique, clean, and easy to find with ample parking. The host was super accommodating with check in, and the are a ton of restaurants and shops within walking distance. Highly recommend. "
The price is €531
includes taxes & fees
2 Oct - 3 Oct
Modern penthouse suite in a restored grain tower with private roof deck.
Spectacular Log Home Estate North Wing Apt
10.0 out of 10, Exceptional, (32)
"Lovely cabin, super clean and quiet. A great alternative to surge pricing at local hotels due to drop off weekend or parents weekend. Thanks. "
Spectacular Log Home Estate North Wing Apt
Beautiful Cozy 2 br in-law apt, prime Hudson Valley location
9.6 out of 10, Exceptional, (13)
"Leisa was immediately responsive when we asked a question pre-booking, and granted a late check-out so we could attend a family event. The ground-floor apartment was easy for our two little dogs to get in & out, the neigborhood was nice for walking them, and the location was very convenient. All in all, a perfect stay."
Beautiful Cozy 2 br in-law apt, prime Hudson Valley location
Walk to WP Gate + Free Parking!
10.0 out of 10, Exceptional, (4)
"Great place! One of the best we have ever been to. Would definitely stay here again!"
Walk to WP Gate + Free Parking!
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
10.0 out of 10, Exceptional, (47)
"This property was very comfortable, clean and had everything we needed. I was able to visit with my West Point Cadet for a weekend and cook a meal for her and we had a lovely time. "
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
Stay in the HEART of West Point~Walk 2 mins to academy!
9.8 out of 10, Exceptional, (26)
"Clean, quiet, and comfortable. Steep stairs as noted in the listing and parking around the corner in back. A couple minor problems, but host was very attentive to helping us solve them."
Stay in the HEART of West Point~Walk 2 mins to academy!
Stay in the heart of Greenwood Lake minutes away from the lake
9.8 out of 10, Exceptional, (18)
"This is an immaculately maintained, tastefully furnished suite. The bedroom can be closed off from the living room and kitchen by a sliding door. The kitchen is easy to use and there's an impressive array of condiments and spices. The shower feels luxurious. The binder of information on hiking, biking, and boating is by far the best we've seen in a vacation rental. Beach passes and beach towels are provided. The owner of the building is a long time resident and operates a cafe out front. You...
Stay in the heart of Greenwood Lake minutes away from the lake
Cozy 1-bedroom retreat minutes from West Point!
10.0 out of 10, Exceptional, (1)
"My daughter and I really enjoyed this property and the property manager was awesome and very responsive. It is a very short drive to West Point which was extremely convenient for us. Very safe and quaint neighborhood."
Cozy 1-bedroom retreat minutes from West Point!
Modern Hudson Valley Apt 202 - King/Queen/Twin
9.6 out of 10, Exceptional, (5)
"This place is literally perfect from the spacious kitchen/living space to the big beautiful bed this place will most likely be our go to."
The price is €276
includes taxes & fees
29 Oct - 30 Oct
Modern Hudson Valley Apt 202 - King/Queen/Twin
Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer
10.0 out of 10, Exceptional, (26)
"Fab location in the heart of Beacon. All of Main Street at our fingertips. Lovely accommodations. It would be nice to have a small but comfortable armchair to pull up with the sofa. "
The price is €244
includes taxes & fees
6 Oct - 7 Oct
Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
10.0 out of 10, Exceptional, (24)
"We had a wonderful three-night stay in Beacon. The location was perfect—right along the main street, walkable to all the retail and restaurants. The unit faced away from the street and was very quiet. It is a charming historic building with original details. Three generous operable windows allow lots of light and air. It was apparent that the host had really thought about what makes a convenient stay—good lighting, a comfortable bed, and all the amenities one might hope for. We loved the...
The price is €238
includes taxes & fees
30 Sept - 1 Oct
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Luxe Studio 2 on Main Street- Luxury Steam Shower- Washer/Dryer, Kitchen
10.0 out of 10, Exceptional, (15)
"Lovely clean studio apartment in the heart of Beacon, definitely recommend this place!"
The price is €256
includes taxes & fees
30 Oct - 31 Oct
Luxe Studio 2 on Main Street- Luxury Steam Shower- Washer/Dryer, Kitchen
East Fishkill Escape, Close to Red Wing Park!
10.0 out of 10, Exceptional, (7)
"An eclectic and open place to relax, take in the scenery, and be well. We took our cadet there to get away from the rigors of West Point for Acceptance Day weekend (it is inside the 20 mile radius). Make use of the outdoor space!"
East Fishkill Escape, Close to Red Wing Park!
Dream getaway apartment in the foot of Gunks Ridge
9.6 out of 10, Exceptional, (15)
"This place was lovely and Serg was great. Not only is the scenery in the surrounding area beautiful but there’s quite a lot to do, especially if you enjoy the outdoors. The property had great ambiance, it was so cozy cute, CLEAN and relaxing. Can’t wait to come back!"
The price is €191
includes taxes & fees
28 Oct - 29 Oct
Dream getaway apartment in the foot of Gunks Ridge
Large Three bedroom apartment, Main St., Goshen
10.0 out of 10, Exceptional, (1)
"Beautifully finished. Roomy and clean. Enjoyed our stay!"
The price is €425
includes taxes & fees
30 Sept - 1 Oct
Large Three bedroom apartment, Main St., Goshen
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Other property types in New Windsor

Beautiful Cozy 2 br in-law apt, prime Hudson Valley location
9.6 out of 10, Exceptional, (13)
"Leisa was immediately responsive when we asked a question pre-booking, and granted a late check-out so we could attend a family event. The ground-floor apartment was easy for our two little dogs to get in & out, the neigborhood was nice for walking them, and the location was very convenient. All in all, a perfect stay."
Beautiful Cozy 2 br in-law apt, prime Hudson Valley location
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
10.0 out of 10, Exceptional, (35)
"Communication and accommodations were great!! Clean place and friendly hosts. "
The price is €451
includes taxes & fees
30 Oct - 31 Oct
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (99)
"Wonderful hilltop location. Beautiful view. Nice apartment. Great hosts. Wish we could have stayed longer! "
The price is €236
includes taxes & fees
1 Oct - 2 Oct
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

What's it like to stay at an apartment in New Windsor?
There are 9 lodging options in New Windsor. Though there aren’t many apartments, we can help you search for similar accommodation. When you search on Expedia, you can use the filters to search for a kitchen— just one of the conveniences you might find in an apartment. You can even filter by similar property types like holiday homes, condos or cabins. Why not visit the shops and take time to enjoy the lakeside while you’re in this family-friendly area? Make time to visit the region’s favourite places such as Woodbury Common Premium Outlets.
How do you know if an apartment is a good option for you?
An apartment is often more spacious than a traditional hotel room and comes with a kitchen, so you can cook some of your meals. Apartments are ideal for families who want the conveniences of home, and also for couples who want something in a quieter part of town.
What's the best apartment for my stay in New Windsor?
Below are some of the favourite apartments in the area: Beautiful Cozy 2 br in-law apt, prime Hudson Valley location: Includes free WiFi, a sofa bed and a Smart TV . Walk to EVERYTHING West Point-2mins to Academy! Mountain Views/private parking: Located 7.9 mi/12.8 km away in Highland Falls . Free WiFi and a Smart TV are included . Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!: It’s situated in Wallkill , 12.6 mi/20.3 km away. Includes free WiFi, a balcony and a Smart TV . Spectacular Log Home Estate North Wing Apt: 8.3 mi/13.3 km away in Marlboro . A balcony, a dining area and a Smart TV are included . Sweet spot studio on village outskirts: It’s located in New Paltz , 18.7 mi/30.1 km from New Windsor. Includes free WiFi, a patio and a Smart TV .
What will the weather be like in New Windsor?
Although weather is just one factor, it can really affect your travel plans, especially if you’re planning an extended stay in New Windsor. The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of 0°C. The snowiest months in New Windsor are January, February, December and March, with each month seeing an average of 14 cm of snowfall.
What should I see and do in New Windsor?
New Windsor is known for its lakeside and shops. Cultural attractions include Knox’s Headquarters State Historic Site and National Purple Heart Hall of Honor, whereas Kristi Babcock Memorial Park and Schunnemunk State Park are a couple of picturesque spots to enjoy the outdoors. In the wider area, you’ll find New Windsor Cantonment State Historic Site and Woodbury Common Premium Outlets.
What's the best way to get to and around New Windsor?
Knowing a bit about the transportation options can make your trip smoother when you get to your destination. Fly into Newburgh, NY (SWF-Stewart Intl.), which is located 3.6 mi (5.8 km) away from the heart of the city. Otherwise, look for flights into Danbury, CT (DXR-Danbury Municipal), which is 28.8 mi (46.3 km) away. If you’d like to explore around the area, consider renting a car to explore more sights.