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Find Romantic Hotels in Ossining, NY from $108

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Check availability on Ossining Romantic Hotels

Our top choices for Ossining romantic hotels

Indoor pool, open 8:30 AM to 9:30 PM, sun loungers
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
4.0 star property
Nanuet
8.8 out of 10, Excellent, (1001)
"Great staff, clean and the pool was awesome! "
Canada
Aleah
$98 nightly
The price is $114
Jan 4 - Jan 5, 2026
Total with taxes and fees
DoubleTree by Hilton Hotel Nanuet
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, (1001)
"Staff was incredibly kind and the room was super cozy. The inn is beautiful and there is enough to do around. "
United States
Ryan
$107 nightly
The price is $122
Jan 11 - Jan 12, 2026
Total with taxes and fees
Overlook Lodge at Bear Mountain
Exterior
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG
3.5 star property
Suffern
8.8 out of 10, Excellent, (1003)
"Good location"
United States
Glenn
$123 nightly
The price is $143
Dec 19 - Dec 20
Total with taxes and fees
Crowne Plaza Suffern - Mahwah by IHG
Dinner served
Ethan Allen Hotel

Ethan Allen Hotel

Ethan Allen Hotel
3.5 star property
Danbury
7.8 out of 10, Good, (1079)
"Great Hotel!"
United States
Steven
$93 nightly
The price is $108
Jan 11 - Jan 12, 2026
Total with taxes and fees
Ethan Allen Hotel
Restaurant
Hotel Nyack, a JdV by Hyatt Hotel

Hotel Nyack, a JdV by Hyatt Hotel

Hotel Nyack, a JdV by Hyatt Hotel
4.0 star property
Nyack
8.6 out of 10, Excellent, (1003)
"Room was clean, staff was pleasant, hotel overall was great"
United States
Cara
$163 nightly
The price is $186
Dec 21 - Dec 22
Total with taxes and fees
Hotel Nyack, a JdV by Hyatt Hotel
Interior
Royal Regency Hotel

Royal Regency Hotel

Royal Regency Hotel
3.5 star property
Northwest Yonkers
8.4 out of 10, Very Good, (2403)
"Hotel was very clean and the staff are great"
United States
Marie and Matt
$99 nightly
The price is $116
Dec 18 - Dec 19
Total with taxes and fees
Royal Regency Hotel
Lobby sitting area
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, (667)
"Location was great & staying at a historic hotel was delightful."
United States
Bobby
$174 nightly
The price is $197
Dec 14 - Dec 15
Total with taxes and fees
The Thayer Hotel at West Point
Free daily self-serve breakfast
Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford
2.5 star property
Elmsford
8.2 out of 10, Very Good, (1458)
"Great experience can’t wait to come back "
United States
Marvin
$123 nightly
The price is $141
Jan 1 - Jan 2, 2026
Total with taxes and fees
Baymont by Wyndham White Plains - Elmsford
Terrace/patio
Hotel NoMa, Trademark Collection by Wyndham

Hotel NoMa, Trademark Collection by Wyndham

Hotel NoMa, Trademark Collection by Wyndham
3.0 star property
New Rochelle
8.2 out of 10, Very Good, (1005)
"Food was good."
United States
Charles
$113 nightly
The price is $129
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hotel NoMa, Trademark Collection by Wyndham
Exterior
Tarrytown House Estate

Tarrytown House Estate

Tarrytown House Estate
3.5 star property
Tarrytown
8.2 out of 10, Very Good, (1000)
"Beautiful property highly recommend if in the area goose feather is a great on site resteraunt as well"
United States
Erek
$175 nightly
The price is $200
Jan 7 - Jan 8, 2026
Total with taxes and fees
Tarrytown House Estate
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 Ossining Hotel Reviews

Hotel NoMa, Trademark Collection by Wyndham

Hotel NoMa, Trademark Collection by Wyndham

10/10 Excellent
"Nice"
Keila 1-night trip
Posted 3 days ago
Hotel NoMa, Trademark Collection by Wyndham

Frequently asked questions

Searching for romantic hotels in Ossining?
Are you in need of a romantic getaway? If you want to explore the area, you might head to Thomas J. Watson Research Center, Sing Sing Prison Museum, or Ossining Historical Society. If you'd like to stay close to a particular destination, you can sort properties by neighborhood or distance to top sights, so you'll be able to see everything on your list.
When is the best time of year for a romantic getaway to Ossining?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Ossining: The hottest months are usually July and August with an average temp of 71°F, while the coldest months are January and February with an average of 34°F. Average annual precipitation for Ossining is 51 inches.
What is there to do in Ossining?
There's nothing better than seeing a new place with your sweetheart, so consider checking out all there is to see and do in Ossining. Thomas J. Watson Research Center, Sing Sing Prison Museum, and Ossining Historical Society are worth a stop when you're out and about.
What's the best way to get to Ossining and around town during my romantic getaway?
These transportation options in Ossining might help your romantic getaway go off without a hitch: If you're looking to fly to Ossining, the closest major airport is Westchester County Airport (HPN), located 10.5 mi (16.8 km) from the city center. If you want to explore the larger area, hop aboard a train at Ossining Station.

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