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Shelter Island Vacation Packages

Build your package with 2 more options

Shelter Island Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Omni Berkshire Place

Omni Berkshire Place

4 out of 5
Save 100% on your flight
Price was $1,394, price is now $866 per person
$866
per person
Oct 14 - Oct 17
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, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions 5th Avenue and Radio City Music Hall are located nearby.
Very nice hotel. Heart of everything. And staff were great. It’s a little dated but so clean and fresh that you don’t really notice any thing. Over all I would stay there again

Reviewed on Aug 26, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $3,272, price is now $1,750 per person
$1,750
per person
Oct 8 - Oct 12
found 23 hours 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.

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 $2,375, price is now $1,278 per person
$1,278
per person
Nov 3 - Nov 10
found 2 days 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.

5th & 55th Residence Club

5th & 55th Residence Club

5 out of 5
Save 100% on your flight
Price was $8,125, price is now $4,801 per person
$4,801
per person
Oct 29 - Nov 3
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 24-hour room service. Popular attractions 5th Avenue and Radio City Music Hall are located nearby.

Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Save 100% on your flight
Price was $1,466, price is now $888 per person
$888
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Stay at this hotel in New York. Enjoy free WiFi, a steam room, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Central Park and Lincoln Center are located nearby.

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
Price was $1,878, price is now $1,140 per person
$1,140
per person
Oct 30 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Book a stay at this golf hotel in Woodbury. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Bethpage Black State Park Golf Course and Oyster Bay Golf Course are located nearby.
Clean room, comfortable bed, great front desk staff and plentiful breakfast!!

Reviewed on Aug 15, 2026

2 bedroom luxury Empire State VIEW

2 bedroom luxury Empire State VIEW

2 out of 5
Save 100% on your flight
Price was $2,624, price is now $1,608 per person
$1,608
per person
Oct 21 - Oct 25
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Stay at this hotel in New York. Enjoy free WiFi, valet parking (surcharge), and in-room washers/dryers. Popular attractions Madison Square Garden and Bryant Park are located nearby.
One of the worst exp here, I have been charged for the trip, got my booking number, driving down to nyc, and was informed they are fully booked, having to wait 3hours to be on the phone to get a hotel room instead.

Reviewed on Aug 23, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Save 100% on your flight
Price was $1,601, price is now $994 per person
$994
per person
Oct 15 - Oct 18
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Stay at this hotel in New York. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Broadway and Rockefeller Center are located nearby.

Shelter Island Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
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 $1,156, price is now $690 per person
$690
per person
Nov 6 - Nov 9
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $3,272, price is now $1,750 per person
$1,750
per person
Oct 8 - Oct 12
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Manhattan
Save 100% on your flight
Price was $1,466, price is now $888 per person
$888
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
2 bedroom luxury Empire State VIEW

2 bedroom luxury Empire State VIEW

2 out of 5
Manhattan
Save 100% on your flight
Price was $2,624, price is now $1,608 per person
$1,608
per person
Oct 21 - Oct 25
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)

Shelter Island Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Save 100% on your flight
Price was $1,769, price is now $991 per person
$991
per person
Nov 3 - Nov 10
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
Price was $4,971, price is now $2,434 per person
$2,434
per person
Oct 14 - Oct 19
found 2 days ago
Roundtrip flight included
Dallas (DFW) 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 $2,375, price is now $1,278 per person
$1,278
per person
Nov 3 - Nov 10
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $2,497, price is now $1,350 per person
$1,350
per person
Oct 29 - Nov 3
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)

Top Flight Deals

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

Breeze Airways
Thu, Sep 10 - Sat, Sep 12
MCO
Orlando Intl.
SWF
Stewart Intl.
$153 Roundtrip, found 1 day ago
$153
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Sep 10 from Orlando Intl. to Stewart Intl., returning Sat, Sep 12, priced at $153 found 1 day ago
Frontier Airlines
Wed, Oct 14 - Mon, Oct 19
MCO
Orlando Intl.
EWR
Newark Liberty Intl. Airport
$153 Roundtrip, found 20 hours ago
$153
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Wed, Oct 14 from Orlando Intl. to Newark Liberty Intl. Airport, returning Mon, Oct 19, priced at $153 found 20 hours ago
Avelo Airlines
Fri, Oct 9 - Mon, Oct 12
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$192 Roundtrip, found 6 days ago
$192
Roundtrip
found 6 days ago
Select Avelo Airlines flight, departing Fri, Oct 9 from Orlando Intl. to Tweed - New Haven Regional, returning Mon, Oct 12, priced at $192 found 6 days ago
Frontier Airlines
Sat, Sep 26 - Tue, Sep 29
FLL
Fort Lauderdale - Hollywood Intl.
LGA
LaGuardia
$211 Roundtrip, found 12 hours ago
$211
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Sat, Sep 26 from Fort Lauderdale - Hollywood Intl. to LaGuardia, returning Tue, Sep 29, priced at $211 found 12 hours ago