Shelter Island Heights Vacations

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

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Shelter Island Heights Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
The Shelburne Sonesta New York

The Shelburne Sonesta New York

4 out of 5
Manhattan
Save 100% on your flight
Price was $701, price is now $371 per person
$371
per person
Feb 15 - Feb 20
found 4 hours ago
Roundtrip flight included
Chicago (ORD) to New York (NYC)
Book a stay at this business-friendly hotel in New York. Enjoy breakfast (surcharge), a health club, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grand Central Terminal and Bryant Park are located nearby.

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was $1,025, price is now $445 per person
$445
per person
Feb 15 - Feb 20
found 13 hours ago
Roundtrip flight included
Chicago (ORD) to New York (NYC)
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 restaurant and the helpful staff in our reviews. Popular attractions Madison Square Garden and Bryant Park are located nearby.

Margaritaville Resort Times Square

Margaritaville Resort Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $868, price is now $455 per person
$455
per person
Feb 15 - Feb 20
found 13 hours ago
Roundtrip flight included
Chicago (ORD) to New York (NYC)
Stay at this hotel in New York. Enjoy breakfast (surcharge), a fitness center, and parking (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Times Square and Bryant Park are located nearby.

Courtyard New York Manhattan/Upper East Side

Courtyard New York Manhattan/Upper East Side

3 out of 5
Manhattan
Price was $971, price is now $520 per person
$520
per person
Feb 15 - Feb 20
found 13 hours ago
Roundtrip flight included
Chicago (ORD) to New York (NYC)
Book a stay at this business-friendly hotel in New York. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Central Park and 5th Avenue are located nearby.

YOTEL New York Times Square

YOTEL New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $701, price is now $377 per person
$377
per person
Feb 15 - Feb 20
found 4 hours ago
Roundtrip flight included
Chicago (ORD) to New York (NYC)
Book a stay at this boutique hotel in New York. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Times Square and Broadway are located nearby.

Millennium Hilton New York One UN Plaza

Millennium Hilton New York One UN Plaza

4 out of 5
Manhattan
Save 100% on your flight
Price was $995, price is now $535 per person
$535
per person
Feb 15 - Feb 20
found 4 hours ago
Roundtrip flight included
Chicago (ORD) to New York (JFK)
Book a stay at this business-friendly hotel in New York. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grand Central Terminal and Bryant Park are located nearby.

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Top Hotel Deals

The Pridwin Hotel

The Pridwin Hotel

4 out of 5
81 Shore Road Shelter Island Heights NY
2.26 km from city center
Book a stay at this beach hotel in Shelter Island Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
The Chequit

The Chequit

3 out of 5
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

Gurney's Montauk Resort & Seawater Spa

4 out of 5
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 ...
Montauk Blue Hotel

Montauk Blue Hotel

2 out of 5
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 parking (surcharge). Popular attractions South Edison Beach and Kirk Park Beach ...
Best Western Niantic - New London/Mystic Area

Best Western Niantic - New London/Mystic Area

2.5 out of 5
265 Flanders Road Niantic CT
32.95 km from city center
Book a stay at this business-friendly hotel in Niantic. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Flanders Plaza Shopping Center ...
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
100 Essex Rd Old Saybrook CT
26.1 km from city center
Book a stay at this business-friendly hotel in Old Saybrook. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Sound View Greenport

Sound View Greenport

4 out of 5
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

Saybrook Point Resort & Marina

3.5 out of 5
2 Bridge St Old Saybrook CT
22.16 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 ...
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
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 Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
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 ...
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
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. ...
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39 Southampton NY
22.53 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 ...
Sleep Inn & Suites Niantic North

Sleep Inn & Suites Niantic North

2.5 out of 5
5 King Arthur Dr Niantic CT
33.01 km from city center
Book a stay at this business-friendly hotel in Niantic. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in ...
Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

3 out of 5
727 Old Montauk Highway Montauk NY
33.79 km from city center
Stay at this hotel in Montauk. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions ...
Sea Crest Resort

Sea Crest Resort

2.5 out of 5
2166 Montauk Hwy Amagansett NY
28.61 km from city center
Book a stay at this beach hotel in Amagansett. Enjoy free WiFi, a beach locale, and a fitness center. Popular attractions Walking Dunes Trailhead and Hither ...
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See all available properties in Shelter Island Heights
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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.

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.

Frontier Airlines
Tue, Jan 13 - Tue, Jan 20
MIA
Miami Intl.
LGA
LaGuardia
$68 Roundtrip, found 6 days ago
$68
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Tue, Jan 13 from Miami Intl. to LaGuardia, returning Tue, Jan 20, priced at $68 found 6 days ago
Spirit Airlines
Thu, Dec 11 - Wed, Dec 31
FLL
Fort Lauderdale - Hollywood Intl.
EWR
Newark Liberty Intl. Airport
$90 Roundtrip, found 2 days ago
$90
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Thu, Dec 11 from Fort Lauderdale - Hollywood Intl. to Newark Liberty Intl. Airport, returning Wed, Dec 31, priced at $90 found 2 days ago
Delta
Fri, Mar 27 - Sat, Mar 28
FLL
Fort Lauderdale - Hollywood Intl.
JFK
John F. Kennedy Intl.
$147 Roundtrip, found 14 hours ago
$147
Roundtrip
found 14 hours ago
Select Delta flight, departing Fri, Mar 27 from Fort Lauderdale - Hollywood Intl. to John F. Kennedy Intl., returning Sat, Mar 28, priced at $147 found 14 hours ago
JetBlue Airways
Tue, Feb 3 - Sun, Feb 8
SJU
Luis Munoz Marin Intl.
EWR
Newark Liberty Intl. Airport
$176 Roundtrip, found 4 days ago
$176
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Tue, Feb 3 from Luis Munoz Marin Intl. to Newark Liberty Intl. Airport, returning Sun, Feb 8, priced at $176 found 4 days ago
American Airlines
Sat, Jan 17 - Tue, Jan 20
SFO
San Francisco Intl.
LGA
LaGuardia
$191 Roundtrip, found 2 days ago
$191
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Jan 17 from San Francisco Intl. to LaGuardia, returning Tue, Jan 20, priced at $191 found 2 days ago