Photo by Wanderlustfemale

Search Villas in New Windsor

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
28 Rab. I - 30 Rab. I
In two weeks
4 Rab. II - 6 Rab. II
In one month
18 Rab. II - 20 Rab. II
In two months
16 Jum. I - 18 Jum. I

Compare 26 Villas in New Windsor with updated reviews, rates, and availability.

Private Estate 9BR w/Pool, Hot Tub & Scenic Views!
Interior

Private Estate 9BR w/Pool, Hot Tub & Scenic Views!

Private Estate 9BR w/Pool, Hot Tub & Scenic Views!
Luxury 5-Bdrm Getaway Near West Point
Property grounds

Luxury 5-Bdrm Getaway Near West Point

3.0 star property
10.0 out of 10, Exceptional, (1)
"This property was fantastic!! The house was beautiful and spacious for our family! The master bathroom had a really cool shower and the kids enjoyed the game room. There were seperate thermostats that everyone can enjoy their own temperature. The views were stunning and the neighborhood was quiet!The host was easy to deal with and communicated in a timely response!!I would highly recommend this property and host! We would totally book again!communit"
Luxury 5-Bdrm Getaway Near West Point
The Scenic Mansion With Breathtaking View
Fridge, microwave, oven, stovetop

The Scenic Mansion With Breathtaking View

9.6 out of 10, Exceptional, (13)
"This house is so grand and perfect for a destination wedding, corprate retreat or family reunion. Host was wonderful!"
The Scenic Mansion With Breathtaking View
MODERN FARMHOUSE HOME ON 5-ACRE DREAM PROPERTY
Fridge, microwave, oven, stovetop

MODERN FARMHOUSE HOME ON 5-ACRE DREAM PROPERTY

9.8 out of 10, Exceptional, (11)
"I loved the house, I'll be back for sure"
MODERN FARMHOUSE HOME ON 5-ACRE DREAM PROPERTY
Kick back & relax in this peaceful, stylish place to stay with the whole family.
Fridge, microwave, oven, stovetop

Kick back & relax in this peaceful, stylish place to stay with the whole family.

10.0 out of 10, Exceptional, (22)
"Our family went to the Hudson Valley area for a wedding. Pre stay communication with Malka was excellent and we all had a wonderful time. Lots of room for the kids to play and be entertained downstairs as well as upstairs in the Projection Room. The backyard was a great soccer area and the fire pit was great to sit around at night. Firewood on site was a real plus! I do recommend to anyone doing substantial cooking for many people to bring their own favorite pots and pans if possible though...
Kick back & relax in this peaceful, stylish place to stay with the whole family.
DREAM Home, Pool, Hot Tub, Game Rm & Mountains.
Exterior

DREAM Home, Pool, Hot Tub, Game Rm & Mountains.

10.0 out of 10, Exceptional, (1)
"This house was absolutely perfect for our friend's weekend wedding. 14 guests, guys/girls in their early to mid 30s. We stayed at this house and attended our friend's rehearsal dinner and wedding about 30 min away. The location is perfect, slightly secluded and quiet. The property is very large and has all the amenities a group of people could want. The interior of the house was clean, setup nicely, and aesthetically pleasing. Everything listed was accurate. The pool and hot tub were clean and...
DREAM Home, Pool, Hot Tub, Game Rm & Mountains.
Luxurious 7 Bedroom Estate with Heated Pool and Hot Tub
Fridge, microwave, oven, stovetop

Luxurious 7 Bedroom Estate with Heated Pool and Hot Tub

2.0 out of 10, (1)
"There was rats inside the house and there was no amenities like toilet paper. And host was very unresponsive."
Luxurious 7 Bedroom Estate with Heated Pool and Hot Tub
Luxurious Villa with pool spa arcade room and more
Outdoor spa tub

Luxurious Villa with pool spa arcade room and more

10.0 out of 10, Exceptional, (5)
"Warm, roomy, and quiet. Lots of room for our family of 5. Communication with host was amazing."
Luxurious Villa with pool spa arcade room and more
Fully facilitated home, 7 Beds + Pool. (Pine Bush)
Private kitchen

Fully facilitated home, 7 Beds + Pool. (Pine Bush)

3.4 out of 10, (3)
"We did not end up staying at this property because the host cancelled on us the day before. He reached out 2 months prior to tell us his pool would not be available and offered us a 20% refund. But he never provided it and did not communicate about this again. When we followed up about it, he cancelled the whole stay and tried to get us to change properties last minute. This seemed very strange so we didn’t agree. We did eventually get a full refund after a LOT of back and forth but lost over...
Fully facilitated home, 7 Beds + Pool. (Pine Bush)
Family Fun Getaway near Cascade Lake in Warwick NY
Fridge, microwave, oven, stovetop

Family Fun Getaway near Cascade Lake in Warwick NY

8.0 out of 10, Very Good, (8)
"The exterior of the home is completely run down. Nothing like the pictures. The interior bedding and furniture is a different set up then depicted. The rugs and carpets are stained and dirty. This did not meet our standards. We would not recommend it to anyone. We left a day early."
Family Fun Getaway near Cascade Lake in Warwick NY
Spacious + beautiful 5-bedroom Mediterranean Villa in Monroe, NY.
Interior

Spacious + beautiful 5-bedroom Mediterranean Villa in Monroe, NY.

2.0 star property
10.0 out of 10, Exceptional, (4)
"Big, spacious and clean. The area is calm and shops are within 5 min driving distance"
Spacious + beautiful 5-bedroom Mediterranean Villa in Monroe, NY.
Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard
Smart TV, fireplace, foosball, table tennis

Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard

9.2 out of 10, Wonderful, (7)
"A spacious house with a to-die-for pool, game room in basement, plenty of storage and refrigerators for all your wonderful culinary desires, comfortable beds, and well divided together and private spaces."
Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard
Perfect home for a dream retreat + POOL
Fridge, microwave, oven, stovetop

Perfect home for a dream retreat + POOL

6.0 out of 10, (2)
"To begin, before leaving for the trip I tried reaching out multiple times for check in information. Upon arrival, I was unable to check into place to stay. I tried multiple times contacting host, as well as support trying to contact the host, with NO answer. This left me to find another place to stay with short notice because we waited for 2+ hours for a reply. Unprofessional, ghosted by the host, and frustrating. This has never happened in all the years I have used Vrbo, but to summarize, do...
Perfect home for a dream retreat + POOL
Luxe Mountain Getaway Fire Pit Arcade Hot Tub Pool
Pool

Luxe Mountain Getaway Fire Pit Arcade Hot Tub Pool

10.0 out of 10, Exceptional, (2)
"Happy Minnewaska is a great place for making memories! Our family really enjoyed our time there, relaxing, hiking in the surrounding area and making s'mores around the campfire. The house is just as pictured, very clean and comfortable. The kitchen is well equipped for basic cooking, which is all we did. It's a bit of a drive into New Paltz, especially on Sunday afternoon, but the town is charming so definitely worth a visit. Hosts were great with communication (though since I prefer to avoid my...
Luxe Mountain Getaway Fire Pit Arcade Hot Tub Pool
Luxurious & Tranquil ~ Pool ~ Fire Pit ~ Backyard!
Miscellaneous

Luxurious & Tranquil ~ Pool ~ Fire Pit ~ Backyard!

6.0 out of 10, (1)
"The pictures are accurate but when you get there you see the furniture is flimsy, the cabinets and drawers fall off when you touch them and the yard is a disaster. There is so much stagnant water the mosquitos look like drones!"
Luxurious & Tranquil ~ Pool ~ Fire Pit ~ Backyard!
Beautiful modern villa with pool suana hot tub...
Property grounds

Beautiful modern villa with pool suana hot tub...

10.0 out of 10, Exceptional, (2)
"My family and I had a wonderful time here! Israel was a great host, messaged me a couple times to make sure everything was okay and if we needed anything. The hot tub and sauna were an awesome addition! It was a great space! Would book again!"
Beautiful modern villa with pool suana hot tub...
Picturesque, Cozy & Fun ~ GameRoom ~ Spacious Yard
Terrace/patio

Picturesque, Cozy & Fun ~ GameRoom ~ Spacious Yard

10.0 out of 10, Exceptional, (1)
"Loved the home didn't realize when booking it was in such a secluded spot so come prepared. House was clean minus some hair in the tubs (around drain) the closet doors attacked my sister (needs to be reinstalled and tightened) upon opening and a few draw coverings fell off. we couldn't find a broom until 10 mins before checkout (we looked all weekend )other wise the place was amazing my sister is already talking about booking in the warmer months because the yard is amazing"
Picturesque, Cozy & Fun ~ GameRoom ~ Spacious Yard
Country Manor at Millers Rock with Pool-1 Hour from NYC
Property grounds

Country Manor at Millers Rock with Pool-1 Hour from NYC

Country Manor at Millers Rock with Pool-1 Hour from NYC
Spacious 1 BR Unit w/ Washer-Dryer and Parking
Fridge, microwave, oven, stovetop

Spacious 1 BR Unit w/ Washer-Dryer and Parking

The price is SAR 285
SAR 585 total
includes taxes & fees
23 Mar - 24 Mar
Spacious 1 BR Unit w/ Washer-Dryer and Parking
Charming 3-bedroom villa with WiFi, AC in fabulous Monroe
Interior

Charming 3-bedroom villa with WiFi, AC in fabulous Monroe

Charming 3-bedroom villa with WiFi, AC in fabulous Monroe
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.
Don't see what you're looking for?
See all available properties in New Windsor
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in New Windsor

Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
Fridge, microwave, oven, stovetop

Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

10.0 out of 10, Exceptional, (45)
"Awesome property. Will visit again. "
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Outdoor dining

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

10.0 out of 10, Exceptional, (2)
"Communication was easy, location and parking was great! Very clean and cozy!"
The price is SAR 971
SAR 1,095 total
includes taxes & fees
21 Mar - 22 Mar
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (108)
"Awesome "
The price is SAR 630
SAR 930 total
includes taxes & fees
24 Mar - 25 Mar
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

Why book your villa in New Windsor with Expedia?
Reserving a villa in New Windsor is as easy as clicking on your travel dates and selecting a place that suits your style. Seeking something low cost or luxurious, or a property that also comes with free WiFi? Use Expedia’s search filters to narrow your results and find your ideal pad.
How can I find cheap villas in New Windsor?
With Expedia’s user-friendly filter tool, reserving cheap villas in New Windsor is a snap. To discover accommodations that give you the most bang for your buck, fine-tune your search by star rating, budget and amenities.