Search Deals on
Ossining Vacation Packages

Build your package with 2 more options

Ossining Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Pergola JFK Airport

Hotel Pergola JFK Airport

2.5 out of 5
Save 100% on your flight
Price was $1,371, price is now $812 per person
$812
per person
Dec 22 - Dec 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Stay at this hotel in Hollis. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Popular attractions Flushing Meadows-Corona Park and UBS Arena are located nearby.

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Save 100% on your flight
Price was $5,964, price is now $3,414 per person
$3,414
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Book a stay at this luxury hotel in New York. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff in our reviews. Popular attractions 5th Avenue and Rockefeller Center are located nearby.

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Save 100% on your flight
Price was $3,247, price is now $1,921 per person
$1,921
per person
Dec 26 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Stay at this hotel in New York. Enjoy free WiFi, a rooftop terrace, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Brooklyn Bridge and Wall Street are located nearby.
Comfortable, clean hotel in Little Italy. Nothing special, but does the job for solo and business travelers. It does have a rooftop deck with great views of the city, especially at night.

Reviewed on Oct 14, 2026

Modern Comfort in the Heart of NYC

Modern Comfort in the Heart of NYC

4 out of 5
Save 100% on your flight
Price was $1,899, price is now $1,126 per person
$1,126
per person
Jan 6 - Jan 12
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
Book a stay at this business-friendly apartment in Yonkers. Enjoy free WiFi, free parking, and dry cleaning or laundry services. Popular attractions Yankee Stadium and Bronx Zoo are located nearby.
LIARS! these people take your money, when you go check in you'll find they aren't the real hosts. and house is already rented long term. NOT A TRUE LISTING!

Reviewed on Oct 14, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $2,431, price is now $1,455 per person
$1,455
per person
Jan 4 - Jan 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Book a stay at this luxury hotel in Brooklyn. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Brooklyn Bridge and Wall Street are located nearby.

The Plaza, A Fairmont Hotel

The Plaza, A Fairmont Hotel

5 out of 5
Save 100% on your flight
Price was $8,201, price is now $5,078 per person
$5,078
per person
Dec 22 - Dec 28
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Book a stay at this luxury hotel in New York. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions 5th Avenue and Radio City Music Hall are located nearby.

Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Save 100% on your flight
Price was $3,504, price is now $2,170 per person
$2,170
per person
Dec 20 - Dec 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Book a stay at this luxury hotel in New York. Enjoy a full-service spa, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grand Central Terminal and 5th Avenue are located nearby.
We have stayed here several times before and we loved it just as much! The staff are very welcoming and helpful. The hotel is beautiful and the bars are unmatched. The location is wonderful for getting to restaurants or sight seeing. We will absolutely stay here again!

Reviewed on Oct 13, 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Save 100% on your flight
Price was $1,439, price is now $906 per person
$906
per person
Nov 17 - Nov 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Book a stay at this business-friendly hotel in New York. Enjoy free breakfast, a fitness center, and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Broadway and Times Square are located nearby.
The room was clean and great overall although a little bit smaller than what we expected, not enough room if you have three luggage like we did. Staff was helpful and pleasant. Breakfast was great with an early morning start @ 6:30am.

Reviewed on Oct 14, 2026

Ossining Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $784, price is now $491 per person
$491
per person
Jan 6 - Jan 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
Price was $5,964, price is now $3,414 per person
$3,414
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $2,927, price is now $1,834 per person
$1,834
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,439, price is now $906 per person
$906
per person
Nov 17 - Nov 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)

Ossining Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $1,428, price is now $840 per person
$840
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Park Lane New York

Park Lane New York

5 out of 5
Manhattan
Price was $4,630, price is now $2,433 per person
$2,433
per person
Dec 8 - Dec 15
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
The Langham, New York, Fifth Avenue

The Langham, New York, Fifth Avenue

5 out of 5
Manhattan
Save 100% on your flight
Price was $2,969, price is now $1,665 per person
$1,665
per person
Jan 6 - Jan 12
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
Price was $5,200, price is now $3,035 per person
$3,035
per person
Dec 2 - Dec 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Allegiant Air
Thu, Dec 3 - Sun, Dec 6
FLL
Fort Lauderdale - Hollywood Intl.
SWF
Stewart Intl.
$100 Roundtrip, found 2 days ago
$100
Roundtrip
found 2 days ago
Select Allegiant Air flight, departing Thu, Dec 3 from Fort Lauderdale - Hollywood Intl. to Stewart Intl., returning Sun, Dec 6, priced at $100 found 2 days ago
Breeze Airways
Thu, Nov 26 - Wed, Dec 2
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$122 Roundtrip, found 11 hours ago
$122
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Thu, Nov 26 from Raleigh - Durham Intl. to Westchester County, returning Wed, Dec 2, priced at $122 found 11 hours ago
Frontier Airlines
Thu, Feb 25 - Sun, Feb 28
DTW
Detroit Metropolitan Wayne County
LGA
LaGuardia
$124 Roundtrip, found 16 hours ago
$124
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Thu, Feb 25 from Detroit Metropolitan Wayne County to LaGuardia, returning Sun, Feb 28, priced at $124 found 16 hours ago
Frontier Airlines
Wed, Nov 4 - Tue, Nov 10
ATL
Hartsfield-Jackson Atlanta Intl.
LGA
LaGuardia
$130 Roundtrip, found 12 hours ago
$130
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Wed, Nov 4 from Hartsfield-Jackson Atlanta Intl. to LaGuardia, returning Tue, Nov 10, priced at $130 found 12 hours ago