Vacation rentals in New Windsor

5 out of 5 average rating, 121 reviews

Home in Greenwood Lake

Escape to the lake!LAKEFRONT/Hot-tub/1 hour to NYC

LauraRating, 5 stars2 weeks ago

Our stay at Starlight Serene was everything we hoped it would be! John was very responsive and helpful, especially as this was our first time using AirBnB. The pictures are very accurate, there were plenty of towels, linens, and a VERY well equipped kitchen - much more than we expected (or I have in my own house, I think!). Lots of nice bonuses to this place - my kids loved the firepit and there was wood on hand as well as a s'mores kit; the hot tub was warm and ready when we arrived. You are at the narrower end of the lake, but still a beautiful view with plenty of wildlife. The location is great - roughly 30ish minutes to Bear Mountain, Legoland, and the Palisades Center (which had tons of rainy-day fun for kids). We even rented a pontoon boat from Murphy's Cove Marina - Richie was really wonderful to us and our kids and they loved their first time boating and fishing on the lake. Thanks for a great experience John!

4.92 out of 5 average rating, 470 reviews

Home in Woodstock

Mountain View Cottage - Sauna, Jacuzzi, Fire Place

NiharRating, 5 stars2 weeks ago

fantastic host and super helpful whenever we had questions. my wife left her iPad there and they mailed it back. verry appreciative of that. first time using a wood fired sauna- I was skittish at first, but it was a great amenity. hot tub was clean and worked well as well. would definitely recommend if you're eyeing a rustic retreat.

4.91 out of 5 average rating, 79 reviews

Townhouse in Hunter

Mountain View Catskill Escape-2 Mins to Slopes!

KaylaRating, 5 stars3 weeks ago

This spot was perfect for the 6 of us! The airbnb matched the photos and the description and we were very comfortable. Unfortunately we went the weekend after ski season ended so a lot of places were on “spring break” and closed in town, but we still had a great time. Highly recommend West Kill Brewing about 20 mins away from the airbnb :)

Cottage in Livingston Manor

4.99 out of 5 average rating, 146 reviews

Cozy mountain top home - views, 5acres & a gym.

NikhilRating, 5 stars2 weeks ago

The cottage was lovely and very comfortable. Simon left us detailed instructions and we had no issues in finding it and settling in. As the weather took a turn for the worse, we spent most of a day cozy in the house. Our dogs were also very comfortable and loved the large backyard. The house decor is very tastefully done, and not only looks great but looks like special effort has been taken to make everything comfortable and easy to use. Thank you for sharing your home!!

4.9 out of 5 average rating, 130 reviews

Home in Middletown

Riverfront! Swim, Fish, Hot Tub & Game Barn.

SamanthaRating, 5 stars1 week ago

Beautiful home in a very private area. Lots of family games and lots of outside things todo. Me and my family had a wonderful Easter weekend get away. Only complaint I would have is the jacuzzi smelled weird and stuff was coming out of the jets but other than that it was perfect! We all were very comfortable and had a blast with the kids.

Cottage in Greenwood Lake

4.92 out of 5 average rating, 89 reviews

Cottage with Picturesque Views

NeelRating, 5 stars2 weeks ago

The place was great - everything we asked for and more. The place exceeded our expectations! The hosts were super nice and welcoming, very responsive - would definitely come here again, and recommend people to check this place out for a getaway weekend at Greenwood Lake

5 out of 5 average rating, 3 reviews

Apartment in Saugerties

Creekfront I Hot Tub I Sauna I Fire Pit I Kayaks

JulietteRating, 5 stars6 months ago

We had a great time staying in this beautiful and comfortable space. It had everything we could hope for and was perfectly clean. The air felt and smelled fresh as we walked in the door. It was spacious and well appointed with extras like condiments, games and puzzles. There was a dog gate and potty bags in case we brought our pets. We didn’t bring ours this time but might in the future because we definitely want to stay here again. There were plenty of clean linens and the shampoo, conditioner and body wash were great. The coffee was delicious and there was tea too. We didn’t use the air fryer, but it was nice to have that and the gas stove in case we wanted to cook. Thank you for a great stay!

5 out of 5 average rating, 13 reviews

Chalet in Craryville

Lockwood Lodge Mountaintop

MichelleRating, 5 stars2 months ago

Lockwood Lodge is a beautiful and peaceful place in a perfect location. Our families loved watching the snow come down from the big windows, the view is spectacular. Our kids loved the vintage video game consoles, the grownups loved the records and games/puzzles, and we all felt right at home in the lovely house. It was a perfect spot to hunker down in the snow storm. Jeremy was incredibly responsive and thoughtful and did much to make sure our stay was perfect. We hope to visit again in the summer to take advantage of the pool, which must be really special against the backdrop of that view.

4.92 out of 5 average rating, 140 reviews

Home in Hopatcong

Lakefront Hopatcong w/dock kayaks fishing near NYC

AmandaRating, 5 stars1 week ago

Had an amazing stay at this beautiful property. It was spacious, clean, and had everything we needed. The host was responsive and super helpful with everything. The views and location were truly incredible. I recommend this house to anyone who is looking to stay in this area.

4.95 out of 5 average rating, 19 reviews

Cabin in Shohola

Rhodo - charming private lake front cabin

ChristinaRating, 5 stars6 months ago

Beautiful property and wonderful hosts who were so accommodating as to drive out to fix the internet for the one member of our group who needed to unfortunately work during our stay. Accommodations were basic and comfortable, which were expected and perfect for our group. We were there on the first chilly weekend of fall and able to spend both nights around the cozy wood stove during the evening and the dock during the day. The lakefront community is beautiful and I hope we can return with our dogs during the summer to take advantage of swimming and kayaking next year.

Vacation rentals for every style

Get the amount of space that is right for you.

Apartments

Convenient locations with everyday essentials

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for New Windsor vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near New Windsor's top sights

Newburgh Brewing Company40 locals recommend

Hudson Taco70 locals recommend

Billy Joe's Ribworks20 locals recommend

Washington's Headquarters State Historic Site36 locals recommend

Ms. Fairfax28 locals recommend

Mama Roux13 locals recommend

Other great vacation rentals in New Windsor

4.96 out of 5 average rating, 185 reviews

Home in Millerton

Vacation Home In Millerton

BettyRating, 5 stars2 weeks ago

We wanted to get away from the city for some peace and quiet and Corina’s place was exactly what we were looking for. It felt very tucked away. The home was stocked with pretty much anything I think one would need. The outdoor space is huge, nice and safe for our dog to frolic. Loved the large firepit - wish we had more time to sit outside. Corina was super friendly, accommodating, and extremely quick to respond to any inquiries, so you should be in good hands if you need any help. I like to try a new airbnb whenever I can, but when we return to Millerton, we’ll be going back to Corina’s!

4.95 out of 5 average rating, 75 reviews

Condo in Vernon Township

Peaceful Mountain Retreat

JulieRating, 5 stars2 weeks ago

Great condo for a family of five. Plenty of space and everything was clean and inviting. our kids especially loved the loft stocked with games and toys.

4.73 out of 5 average rating, 112 reviews

Condo in Vernon Township

200 yds Minerals - great for hotel weddings

CindyRating, 5 stars1 week ago

The place was great and just as pictured/described. Joann gave great instructions and was very responsive. We were only there for a short stay for a race, but it looked like a great area I would’ve loved to explore if we had more time. The only thing I didn’t care for was the requirement for to wash and dry all towels before leaving. Since I already paid a hefty cleaning fee that seemed like a bit much. And the washer/dryer is small so this took a couple of loads to get done.

Cottage in Greenwood Lake

4.96 out of 5 average rating, 48 reviews

5 bedroom 7 beds Cottage Sauna, Hike, Winery & Ski

JasonRating, 5 stars2 weeks ago

We had a great time at Carmine's place, highly recommend.

4.99 out of 5 average rating, 104 reviews

Cabin in Shandaken

A Place Called Home in The Catskill

KateRating, 5 stars1 month ago

We just finished a two month rental of John’s wonderful home. Our family of 5 used the home primarily on the weekends when we were enjoying ski season at Belleayre Mountain. I can’t say enough great things about this home. Our family felt totally at home - every aspect was perfectly maintained and the home maximized comfort. Our favorite part of the home was the great room where we would watch movies on the huge family sofa in front of a crackling fire. It was the perfect way to end a day of skiing. Our kids loved the downstairs family room with the foosball table and there were lots of games to play and keep everyone busy and entertained. And the kitchen is huge and very well stocked with all the appliances you will ever need. So it was a fantastic 2 months and we look forward to renting this property again!

4.93 out of 5 average rating, 29 reviews

Home in Tannersville

Luxury Spacious Private Home w/tub! Enjoy Spring

JosephRating, 5 stars2 days ago

The hot tub in our original booking broke the day before we checked in and the hosts were great and let us switch to this location with a hot tub. It was clean and great for our family! We had a blast

4.73 out of 5 average rating, 158 reviews

Chalet in Fleischmanns

Sauna equipped Belleayre Cozy Cabin

ChloeRating, 5 stars2 months ago

Perfect for a ski weekend. Sauna is great, and location cannot be beat.