New Windsor Vacation Homes

A large suspension bridge at night with illuminated cables and a central tower.

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Our top choices for New Windsor holiday homes

House on the Babbling Brook- Quiet 2BR + King Bed!

Highland Falls

Scott G.

HK$3,137 total

includes taxes & fees

1 Aug - 2 Aug

River Views & Hot Tub | Riverview on Washington

Newburgh

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

Cornwall

Elisabeth

HK$3,140 total

includes taxes & fees

29 Jul - 30 Jul

3BR West Point Retreat-3min to Back Gate+ King Bed

Highland Falls

Christine T.

HK$3,851 total

includes taxes & fees

29 Jul - 30 Jul

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

Fishkill

Brian

HK$2,534 total

includes taxes & fees

30 Jul - 31 Jul

Large,Cozy,Bright Apartment, Business Themed.

Newburgh

Adhith P.

HK$4,817 total

includes taxes & fees

22 Aug - 23 Aug

Lovely 3BR Home with parking-Walk to WP Gate!

Highland Falls

Briana T.

HK$2,968 total

includes taxes & fees

29 Jul - 30 Jul

Perfect and Spacious Hudson Valley Escape!

Cornwall

Joseph S.

HK$6,457 total

includes taxes & fees

29 Jul - 30 Jul

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Top New Windsor Hotel Reviews

DoubleTree by Hilton Poughkeepsie Convention Center

8/10 Good

"Stayed at Doubletree for 6 days. Easy check-in, room was clean and spacious. Front desk associate was friendly and helpful. Had dinner in restaurant 1-night and take-out 1-night, good food and service. Had breakfast most mornings. Food was good. One day our room was cleaned and ready for us at 4:30 which was an inconvenience because we were meeting friends for dinner at 5:00 so we were late. The next day our room wasn't cleaned at all. Front desk stated that 3 staff had called out sick and everyone was gone for the day. We got clean towels. The next day, we went out and returned to our room at 6:00 and our room once again was not cleaned at all. No reason given. This was a big disappointment. Spent a little time at bar since they weren't always opened. Elevators a bit complicated and found out that some quests, including us, were not aware of the fact that quests had to switch elevators to go up and down. Would stay here again but cleaning room service needs to do better."

Overlook Lodge at Bear Mountain

8/10 Good

"We stayed in one of the stone cottages and were given two keys to our room and only one of the two worked. Walls are pretty thin you could hear other people's conversations. The room itself was cozy and clean and has a romantic vibe making it an ideal location for a weekend getaway with your partner."

Quality Inn Poughkeepsie

8/10 Good

"Staff, room and parking were great. Breakfast was very disappointing. Space is part of the problem and the coffee maker wasn't working, so staff was having to refill a thermo container. Food choices were very limited mainly due to the space. Its also not practical to have the single desk staff also dealing with the breakfast. Again,room and staff were great. I didn't use the pool or other amenities"

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