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Find Romantic Hotels in New Windsor, NY

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Check availability on New Windsor Romantic Hotels

Our top choices for New Windsor romantic hotels

Restaurant
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1000)
"Staff was incredibly kind and the room was super cozy. The inn is beautiful and there is enough to do around. "
United States
Ryan
The price is AED 389
AED 440 total
includes taxes & fees
17 Dec - 18 Dec
Overlook Lodge at Bear Mountain
Bar (on property)
DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center
4.0 star property
Downtown Poughkeepsie
8.4 out of 10, Very Good, (1000)
"Courteous staff, clean and well outfitted rooms, nice breakfast buffet. "
United States
Kaye
The price is AED 358
AED 419 total
includes taxes & fees
18 Dec - 19 Dec
DoubleTree by Hilton Poughkeepsie Convention Center
Exterior detail
Borland House Inn

Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (144)
"Had a great stay at the the Borland House Inn a historical setting in a cute town with wonderful staff and a delicious breakfast"
United States
Deborah
Borland House Inn
Exterior
Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG
2.5 star property
Poughkeepsie
8.6 out of 10, Excellent, (1000)
"Great breakfast, very nice staff, clean room."
United States
Lisa
The price is AED 371
AED 431 total
includes taxes & fees
4 Jan - 5 January 2026
Holiday Inn Express Poughkeepsie by IHG
Bar (on property)
The Thayer Hotel at West Point

The Thayer Hotel at West Point

The Thayer Hotel at West Point
3.5 star property
West Point
9.0 out of 10, Wonderful, (666)
"Location was great & staying at a historic hotel was delightful."
United States
Bobby
The price is AED 559
AED 728 total
includes taxes & fees
14 Dec - 15 Dec
The Thayer Hotel at West Point
BBQ/picnic area
SpringHill Suites by Marriott Fishkill

SpringHill Suites by Marriott Fishkill

SpringHill Suites by Marriott Fishkill
3.0 star property
Fishkill
9.6 out of 10, Exceptional, (999)
"This was a clean and convenient hotel for visiting the Hudson Valley to see the foliage. We were able to visit beautiful Beacon as well as Storm King Art Center which was about 20 minutes away. We would definitely stay again."
United States
Garvin
The price is AED 511
AED 578 total
includes taxes & fees
28 Dec - 29 Dec
SpringHill Suites by Marriott Fishkill
Courtyard
Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown
3.0 star property
Middletown
9.0 out of 10, Wonderful, (744)
"Overall, it was a good one-night stay. The room was clean and spacious, and parking was convenient. However, the breakfast needs significant improvement; the coffee, eggs, and bacon were all served cold. Additionally, the dining area lacked short tables for children to comfortably sit and eat."
United States
JENNY
The price is AED 526
AED 634 total
includes taxes & fees
22 Dec - 23 Dec
Home2 Suites by Hilton Middletown
View from property
Residence Inn by Marriott Middletown Goshen

Residence Inn by Marriott Middletown Goshen

Residence Inn by Marriott Middletown Goshen
3.0 star property
Middletown
9.4 out of 10, Exceptional, (317)
"Room and service were excellent."
United States
Cymantha
The price is AED 624
AED 738 total
includes taxes & fees
28 Dec - 29 Dec
Residence Inn by Marriott Middletown Goshen
Premium bedding, down comforters, minibar, in-room safe
Wildflower Farms, Auberge Collection

Wildflower Farms, Auberge Collection

Wildflower Farms, Auberge Collection
5.0 star property
Gardiner
9.4 out of 10, Exceptional, (56)
"Great stay"
United States
Adrienne
The price is AED 3,306
AED 3,862 total
includes taxes & fees
11 Dec - 12 Dec
Wildflower Farms, Auberge Collection
Exterior
Villa Verde BB Greenwood Lake NY

Villa Verde BB Greenwood Lake NY

Villa Verde BB Greenwood Lake NY
4.0 star property
Monroe
10.0 out of 10, Exceptional, (13)
"Amazing breakfast, scenery, tucked away on a hilltop, what a getaway! "
United States
Gary
The price is AED 629
AED 785 total
includes taxes & fees
11 Dec - 12 Dec
Villa Verde BB Greenwood Lake NY
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.
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Top New Windsor Hotel Reviews

Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

10/10 Excellent
"Clean, people very nice, thank you."
Aaron 2-night trip
Posted 4 days ago
Hampton Inn & Suites Poughkeepsie

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Frequently asked questions

Searching for romantic hotels in New Windsor?
Are you and your partner looking for a romantic vacation? Our guests also enjoy New Windsor for its shopping, restaurants, and lakeside setting. If you'd like to explore some of the area's notable sights, you might make a stop by National Purple Heart Hall of Honor, New Windsor Cantonment State Historic Site, or Knox's Headquarters State Historic Site. If you'd like to stay close to a certain attraction, you can sort by neighborhood and proximity to top sights, so you and your partner will get to see everything on your list.
When is the best time of year for a romantic getaway to New Windsor?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in New Windsor: The hottest months are usually July and August with an average temp of 69°F, while the coldest months are January and February with an average of 32°F. The snowiest months in New Windsor are January, February, December, and March, with each month seeing an average of 6 inches of snowfall.
What is there to do in New Windsor?
There's nothing better than wandering around a new destination with your sweetheart, so consider checking out all there is to see and do in New Windsor. Couples looking for a little of everything will enjoy New Windsor for its shopping, restaurants, and lakeside setting. You might think about stopping by National Purple Heart Hall of Honor, New Windsor Cantonment State Historic Site, or Knox's Headquarters State Historic Site while you're seeing the sights.
What's the best way to get to New Windsor and around town during my romantic getaway?
This information about transportation options in New Windsor might help your romantic getaway go off without a hitch: The closest major airport is Stewart Intl. Airport (SWF), located 3.6 mi (5.8 km) from the city center. If you'd like to venture out around the area, you may want a rental car for your journey.