Shelter Island Heights Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Shelter Island Heights Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Chelsea Savoy Hotel
Manhattan
Price was $651, price is now $535 per person
$535
per person
Jan 5 - Jan 9
found 20 hours ago
Roundtrip flight included
Chicago (ORD) to New York (JFK)
Stay at this hotel in New York. Enjoy free breakfast, free WiFi, and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Madison Square Garden and Bryant Park are located nearby.
The staff were friendly and the room was clean and quiet! Delicious NY bagels and muffins for breakfast! A perfect location to go to MSG for a show!
Reviewed on Nov 14, 2026
Hotel Riu Plaza New York Times Square
Manhattan
Save 100% on your flight
Price was $1,119, price is now $760 per person
$760
per person
Jan 5 - Jan 9
found 20 hours ago
Roundtrip flight included
Chicago (ORD) 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.
We had a wonderful stay! The hotel was very clean, the staff was friendly and welcoming, and our spacious, beautiful room was ready before check in time. The complimentary breakfast offered a great variety of options. The location was perfect close to Times Square and within walking distance of restaurants, nightlife, and the Theater District. We truly enjoyed our stay and would definitely stay here again! Highly recommend!
Reviewed on Nov 14, 2026
Hotel St. James
Manhattan
Price was $801, price is now $599 per person
$599
per person
Jan 5 - Jan 9
found 20 hours ago
Roundtrip flight included
Chicago (ORD) to New York (JFK)
Stay at this hotel in New York. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Times Square and Broadway are located nearby.
The room was very clean, the staff was friendly and helpful. No bar or restaurant on site but both were on the same block. Convenience store next door has very good coffee. Hotel has no amenities. Old style radiator heat can’t be adjusted
Reviewed on Nov 14, 2026
The St. Regis New York
Manhattan
Save 100% on your flight
Price was $2,655, price is now $1,989 per person
$1,989
per person
Jan 5 - Jan 9
found 20 hours ago
Roundtrip flight included
Chicago (ORD) to New York (JFK)
Book a stay at this luxury hotel in New York. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Popular attractions 5th Avenue and Radio City Music Hall are located nearby.
The managers need complete retraining or higher managers that are way more capable in dealing with customers and not fighting and arguing with them and telling them they’re wrong
Reviewed on Nov 6, 2026
Motto By Hilton New York City Times Square
Manhattan
Price was $689, price is now $574 per person
$574
per person
Jan 5 - Jan 9
found 20 hours ago
Roundtrip flight included
Chicago (ORD) to New York (JFK)
Stay at this hotel in New York. Enjoy free WiFi, a fitness center, and a 24-hour front desk. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Broadway and Rockefeller Center are located nearby.
Hampton Inn New York Times Square
Manhattan
Price was $805, price is now $698 per person
$698
per person
Jan 5 - Jan 9
found 20 hours ago
Roundtrip flight included
Chicago (ORD) to New York (JFK)
Stay at this hotel in New York. Enjoy free breakfast, free WiFi, and valet parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Broadway and Times Square are located nearby.
Great location to the event we were attending
Reviewed on Nov 14, 2026
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See all available trips from Columbus to Shelter Island Heights
View all tripsTop Hotel Deals
The Chequit
23 Grand Ave Shelter Island Heights NY
0.07 km from city center
Stay at this hotel in Shelter Island Heights. Enjoy free WiFi, free parking, and premium bedding. Popular attractions Shelter Island Country Club and Sunset ...
Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway Montauk NY
31.46 km from city center
Book a stay at this beach resort in Montauk. Enjoy an outdoor pool, a full-service spa, and 2 restaurants. Popular attractions Hither Woods Preserve and Hither ...
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
22.9 km from city center
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
22.98 km from city center
Book a stay at this beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
The Atlantic Hotel
1655 County Road 39 Southampton NY
22.5 km from city center
Stay at this hotel in Southampton. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
Offshore Montauk
71 S Emerson Ave Montauk NY
34.71 km from city center
Stay at this hotel in Montauk. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Montauk Point Lighthouse and Montauk Point are located ...
Montauk Blue Hotel
108 South Emerson Avenue Montauk NY
34.97 km from city center
Book a stay at this beach hotel in Montauk. Enjoy free WiFi, a beach locale, and daily housekeeping. Popular attractions Montauk Point Lighthouse and Montauk ...
Montauk Yacht Club
32 Star Island Rd Montauk NY
35.46 km from city center
Book a stay at this luxury hotel in Montauk. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the property condition ...
The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
23.01 km from city center
Book a stay at this business-friendly hotel in Southampton. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
Ocean Resort Inn
95 S Emerson Ave Montauk NY
34.87 km from city center
Book a stay at this beach motel in Montauk. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our ...
Zey Hotel
439 Main Street Greenport NY
2.31 km from city center
Book a stay at this boutique hotel in Greenport. Enjoy free parking, free bicycles on site, and daily housekeeping. Popular attractions Greenport Harbor Brewing ...
Sound View Greenport
58775 County Rd 48 Greenport NY
3.7 km from city center
Book a stay at this beach hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
Saybrook Point Resort & Marina
2 Bridge St Old Saybrook CT
22.2 km from city center
Book a stay at this spa hotel in Old Saybrook. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the restaurant and the helpful staff in ...
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See all available properties in Shelter Island Heights
View all propertiesLowest 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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Wed, Feb 10 - Tue, Feb 23
MCO
Orlando Intl.
EWR
Newark Liberty Intl. Airport
$148 Roundtrip, found 3 days ago
$148
Roundtrip
found 3 days ago
Sat, Dec 5 - Wed, Dec 9
FLL
Fort Lauderdale - Hollywood Intl.
LGA
LaGuardia
$199 Roundtrip, found 2 days ago
$199
Roundtrip
found 2 days ago
Wed, Jan 6 - Sun, Jan 17
MIA
Miami Intl.
JFK
John F. Kennedy Intl.
$209 Roundtrip, found 3 days ago
$209
Roundtrip
found 3 days ago
Thu, Dec 10 - Mon, Dec 14
FLL
Fort Lauderdale - Hollywood Intl.
EWR
Newark Liberty Intl. Airport
$219 Roundtrip, found 6 days ago
$219
Roundtrip
found 6 days ago
Thu, Jan 7 - Sun, Jan 10
MCO
Orlando Intl.
SWF
Stewart Intl.
$248 Roundtrip, found 3 days ago
$248
Roundtrip
found 3 days ago