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

Compare 21 Villas in New Windsor with updated reviews, rates, and availability.

MODERN FARMHOUSE HOME ON 5-ACRE DREAM PROPERTY
Private kitchen

MODERN FARMHOUSE HOME ON 5-ACRE DREAM PROPERTY

9.2 out of 10, Wonderful, (5)
"Simple easy accommodation. A bit smaller than anticipated but functioned very well for our group"
MODERN FARMHOUSE HOME ON 5-ACRE DREAM PROPERTY
Kick back & relax in this peaceful, stylish place to stay with the whole family.
Aerial view

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

10.0 out of 10, Exceptional, (21)
"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.
Luxurious Villa with pool spa arcade room and more
Living area

Luxurious Villa with pool spa arcade room and more

10.0 out of 10, Exceptional, (4)
"Me and my family enjoyed everything about this property and cant wait to dtay here again ."
Luxurious Villa with pool spa arcade room and more
The Scenic Mansion With Breathtaking View
Property grounds

The Scenic Mansion With Breathtaking View

9.6 out of 10, Exceptional, (11)
"So nice we keep coming back. Can't recommend highly enough and will be back in the spring. "
The Scenic Mansion With Breathtaking View
DREAM Home, Pool, Hot Tub, Game Rm & Mountains.

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.
Awesome Country Retreat - 4BR - Private and Peaceful
Living area

Awesome Country Retreat - 4BR - Private and Peaceful

9.8 out of 10, Exceptional, (10)
"We loved this house. It was perfect for our purposes. We hosted the rehearsal dinner for our son's wedding. It was a drop-in style event so lots of people mingling. The downstairs space was open with lots of natural light. We also made use of the side deck since the weather was beautiful. The house was very clean and there were more emenities provided than I have seen in other places. The only issue we had was that there was no closet in the master bedroom. There were two ironing boards, so we...
Awesome Country Retreat - 4BR - Private and Peaceful
Family Fun Getaway near Cascade Lake in Warwick NY
Exterior

Family Fun Getaway near Cascade Lake in Warwick NY

9.0 out of 10, Wonderful, (7)
"Our family really enjoyed our stay in this house! The game room especially was a big hit! We would definitely love to come back here again soon!"
Family Fun Getaway near Cascade Lake in Warwick NY
Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard
Front of Property

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
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...
Perfect home for a dream retreat + POOL
Living area

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
Luxurious & Tranquil ~ Pool ~ Fire Pit ~ Backyard!
Living area

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!
Lakeside Haven - Ultimate Relaxation Spot
Exterior

Lakeside Haven - Ultimate Relaxation Spot

7.0 out of 10, Good, (6)
"Very good for family and friends celebrating or reunions. We all have a good time."
Lakeside Haven - Ultimate Relaxation Spot
Luxe Mountain Getaway Fire Pit Arcade Hot Tub Pool
Outdoor dining

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

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

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

Country Manor at Millers Rock with Pool-1 Hour from NYC
Spacious + beautiful 5-bedroom Mediterranean Villa in Monroe, NY.
Front Yard

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

2.0 star property
10.0 out of 10, Exceptional, (3)
"The villa was beautiful, the host was responsive, my friends and I had a very relaxing and productive time!"
Spacious + beautiful 5-bedroom Mediterranean Villa in Monroe, NY.
Picturesque, Cozy & Fun ~ GameRoom ~ Spacious Yard
Living area

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
Updated 3 to 4 bedroom Cape Cod
Interior

Updated 3 to 4 bedroom Cape Cod

Updated 3 to 4 bedroom Cape Cod
Charming 2-bedroom villa in serene Holmes with AC, WiFi
Living area

Charming 2-bedroom villa in serene Holmes with AC, WiFi

2.0 star property
Charming 2-bedroom villa in serene Holmes with AC, WiFi
5 Bdrm luxury near west point with gym, game room and more

5 Bdrm luxury near west point with gym, game room and more

3.0 star property
5 Bdrm luxury near west point with gym, game room and more
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.
Private kitchen

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

10.0 out of 10, Exceptional, (40)
"We loved our two nights here! Space was spotless and comfortable for 4 of us. Location was central to everything. "
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
Beautiful Cozy 2 br in-law apt, prime Hudson Valley location
Living area

Beautiful Cozy 2 br in-law apt, prime Hudson Valley location

9.6 out of 10, Exceptional, (15)
"The location was convenient for our purposes; neighbourhood felt safe. The place was clean, the beds were comfortable. The kitchen was well equipped. The sofas were not comfortable to lounge on."
Beautiful Cozy 2 br in-law apt, prime Hudson Valley location
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Autumn Foliage - Private Patio View

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (105)
"Super cozy apartment with a beautiful view. Very welcoming host and a great place for a short stay near Bear Mountain. "
The price is AED 617
AED 915 total
includes taxes & fees
30 Nov - 1 Dec
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?
We think organizing a vacation should be a breeze, so if you’re on the lookout for villas at a great price, Expedia is here to help. Save those pennies and select an all-inclusive stay, or splurge on a luxury villa to treat your sweetheart. Our handy filters make it easy to secure a property in New Windsor that fits your needs.
How can I find cheap villas in New Windsor?
The best way to get cheap villas in New Windsor is with Expedia’s filter tool. Refine your search by amenities, budget and star rating to secure unbeatable deals in just a click or two.