Cheap Vacations in Shelter Island

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3-night Shelter Island vacations

Price found within the past 48 hours. Click for updated prices.
Windrose On Hudson

Windrose On Hudson

3 out of 5
Save 100% on your flight
Price was $614, price is now $416 per person
$416
per person
Apr 30 - May 3
found 18 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to New York (LGA)
Margaritaville Resort Times Square

Margaritaville Resort Times Square

4 out of 5
Save 100% on your flight
Price was $860, price is now $515 per person
$515
per person
Apr 6 - Apr 9
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Newark Liberty Intl. Airport (EWR)
Topping Rose House

Topping Rose House

4.5 out of 5
Save 100% on your flight
Price was $1,394, price is now $859 per person
$859
per person
Apr 15 - Apr 18
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Save 100% on your flight
Price was $1,333, price is now $833 per person
$833
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Hotel St. James

Hotel St. James

2.5 out of 5
Save 100% on your flight
Price was $747, price is now $479 per person
$479
per person
Apr 6 - Apr 9
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Newark Liberty Intl. Airport (EWR)
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Save 100% on your flight
Price was $1,393, price is now $907 per person
$907
per person
Apr 6 - Apr 9
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Newark Liberty Intl. Airport (EWR)
Hyatt Grand Central New York

Hyatt Grand Central New York

4 out of 5
Save 100% on your flight
Price was $644, price is now $421 per person
$421
per person
Apr 6 - Apr 9
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Newark Liberty Intl. Airport (EWR)
Outsite Chelsea

Outsite Chelsea

2 out of 5
Save 100% on your flight
Price was $695, price is now $458 per person
$458
per person
Apr 6 - Apr 9
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Newark Liberty Intl. Airport (EWR)
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Save 100% on your flight
Price was $1,049, price is now $692 per person
$692
per person
Apr 6 - Apr 9
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Newark Liberty Intl. Airport (EWR)
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 $981, price is now $650 per person
$650
per person
Apr 6 - Apr 9
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Newark Liberty Intl. Airport (EWR)
Hyatt Union Square New York

Hyatt Union Square New York

4 out of 5
Save 100% on your flight
Price was $1,274, price is now $857 per person
$857
per person
Apr 21 - Apr 24
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Newark Liberty Intl. Airport (EWR)

4-night Shelter Island vacations

Price found within the past 48 hours. Click for updated prices.
Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Save 100% on your flight
Price was $842, price is now $564 per person
$564
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Newark Liberty Intl. Airport (EWR)
Margaritaville Resort Times Square

Margaritaville Resort Times Square

4 out of 5
Price was $1,309, price is now $643 per person
$643
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Newark Liberty Intl. Airport (EWR)
Hotel St. James

Hotel St. James

2.5 out of 5
Save 100% on your flight
Price was $1,041, price is now $567 per person
$567
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Newark Liberty Intl. Airport (EWR)
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Price was $1,255, price is now $809 per person
$809
per person
Apr 16 - Apr 20
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Newark Liberty Intl. Airport (EWR)
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Save 100% on your flight
Price was $1,310, price is now $848 per person
$848
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Newark Liberty Intl. Airport (EWR)
Hyatt Union Square New York

Hyatt Union Square New York

4 out of 5
Price was $1,241, price is now $806 per person
$806
per person
Apr 16 - Apr 20
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Newark Liberty Intl. Airport (EWR)
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Save 100% on your flight
Price was $1,485, price is now $971 per person
$971
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Newark Liberty Intl. Airport (EWR)
Outsite Chelsea

Outsite Chelsea

2 out of 5
Save 100% on your flight
Price was $1,098, price is now $730 per person
$730
per person
Apr 22 - Apr 26
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Newark Liberty Intl. Airport (EWR)
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Save 100% on your flight
Price was $2,581, price is now $1,726 per person
$1,726
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
Millennium Hotel Broadway Times Square

Millennium Hotel Broadway Times Square

4 out of 5
Save 100% on your flight
Price was $883, price is now $592 per person
$592
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Newark Liberty Intl. Airport (EWR)
Hotel Stanford

Hotel Stanford

3 out of 5
Save 100% on your flight
Price was $1,005, price is now $685 per person
$685
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Newark Liberty Intl. Airport (EWR)

5-night Shelter Island vacations

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Long Island City New York

Hilton Garden Inn Long Island City New York

3 out of 5
Save 100% on your flight
Price was $1,053, price is now $734 per person
$734
per person
Apr 13 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to New York (JFK)
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Save 100% on your flight
Price was $2,077, price is now $1,182 per person
$1,182
per person
Apr 13 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
The William Hotel Midtown, New York

The William Hotel Midtown, New York

2 out of 5
Save 100% on your flight
Price was $2,130, price is now $1,265 per person
$1,265
per person
Apr 13 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $1,492, price is now $911 per person
$911
per person
Apr 29 - May 4
found 14 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (JFK)
Newark Liberty International Airport Marriott

Newark Liberty International Airport Marriott

4 out of 5
Price was $1,202, price is now $758 per person
$758
per person
Apr 23 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Save 100% on your flight
Price was $1,703, price is now $1,075 per person
$1,075
per person
Apr 13 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Empire Hotel

Empire Hotel

4 out of 5
Save 100% on your flight
Price was $1,230, price is now $801 per person
$801
per person
Apr 13 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Holiday Inn Express New York City Times Square by IHG

Holiday Inn Express New York City Times Square by IHG

3 out of 5
Save 100% on your flight
Price was $1,092, price is now $737 per person
$737
per person
Apr 13 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Hard Rock Hotel New York

Hard Rock Hotel New York

4.5 out of 5
Save 100% on your flight
Price was $1,348, price is now $930 per person
$930
per person
Apr 13 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
New York Marriott Marquis

New York Marriott Marquis

4.5 out of 5
Save 100% on your flight
Price was $1,369, price is now $945 per person
$945
per person
Apr 13 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Hyatt Union Square New York

Hyatt Union Square New York

4 out of 5
Price was $1,717, price is now $1,187 per person
$1,187
per person
Apr 14 - Apr 19
found 17 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Interfaith 21

Interfaith 21

2 out of 5
Price was $1,450, price is now $1,006 per person
$1,006
per person
Apr 29 - May 4
found 14 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)

6-7 night Shelter Island vacations

Price found within the past 48 hours. Click for updated prices.
Paramount Times Square – A Generator Hotel

Paramount Times Square – A Generator Hotel

4 out of 5
Save 100% on your flight
Price was $927, price is now $615 per person
$615
per person
Apr 22 - Apr 28
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Hotel St. James

Hotel St. James

2.5 out of 5
Price was $1,441, price is now $726 per person
$726
per person
Apr 22 - Apr 28
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Save 100% on your flight
Price was $1,160, price is now $674 per person
$674
per person
Apr 22 - Apr 28
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Outsite Chelsea

Outsite Chelsea

2 out of 5
Save 100% on your flight
Price was $1,409, price is now $845 per person
$845
per person
Apr 22 - Apr 28
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Save 100% on your flight
Price was $1,999, price is now $1,219 per person
$1,219
per person
Apr 22 - Apr 28
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Court Square Hotel Long Island City New York , Belvilla District 6 Formerly Sonder

Court Square Hotel Long Island City New York , Belvilla District 6 Formerly Sonder

3.5 out of 5
Save 100% on your flight
Price was $1,504, price is now $953 per person
$953
per person
Apr 16 - Apr 23
found 24 hours ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Millennium Hotel Broadway Times Square

Millennium Hotel Broadway Times Square

4 out of 5
Save 100% on your flight
Price was $1,236, price is now $784 per person
$784
per person
Apr 22 - Apr 28
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Candlewood Suites New York City-Times Square by IHG

Candlewood Suites New York City-Times Square by IHG

2.5 out of 5
Save 100% on your flight
Price was $1,301, price is now $848 per person
$848
per person
Apr 22 - Apr 28
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Hotel Stanford

Hotel Stanford

3 out of 5
Save 100% on your flight
Price was $1,388, price is now $917 per person
$917
per person
Apr 22 - Apr 28
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Comfort Inn Prospect Park - Brooklyn

Comfort Inn Prospect Park - Brooklyn

2.5 out of 5
Save 100% on your flight
Price was $1,235, price is now $834 per person
$834
per person
Apr 14 - Apr 21
found 24 hours ago
Roundtrip flight included
Chicago (ORD) to New York (JFK)
PUBLIC, an Ian Schrager hotel

PUBLIC, an Ian Schrager hotel

4 out of 5
Save 100% on your flight
Price was $1,649, price is now $1,118 per person
$1,118
per person
Apr 22 - Apr 28
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Save 100% on your flight
Price was $2,434, price is now $1,703 per person
$1,703
per person
Apr 5 - Apr 11
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)

Flight deals to Shelter Island

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

Fri, May 8 - Wed, May 13
ATL
Atlanta
LGA
New York
$56 Roundtrip, found 1 day ago
$56
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, May 8 from Atlanta to New York, returning Wed, May 13, priced at $56 found 1 day ago
Mon, Mar 23 - Tue, Mar 24
ATL
Atlanta
JFK
New York
$56 Roundtrip, found 3 days ago
$56
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Mar 23 from Atlanta to New York, returning Tue, Mar 24, priced at $56 found 3 days ago
Fri, Apr 24 - Sun, Apr 26
ATL
Atlanta
EWR
New York
$56 Roundtrip, found 5 hours ago
$56
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Fri, Apr 24 from Atlanta to New York, returning Sun, Apr 26, priced at $56 found 5 hours ago
Fri, May 15 - Sat, May 16
MCO
Orlando
LGA
New York
$66 Roundtrip, found 19 hours ago
$66
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Fri, May 15 from Orlando to New York, returning Sat, May 16, priced at $66 found 19 hours ago
Thu, May 7 - Mon, May 11
MCO
Orlando
EWR
New York
$77 Roundtrip, found 1 day ago
$77
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, May 7 from Orlando to New York, returning Mon, May 11, priced at $77 found 1 day ago
Sat, May 9 - Tue, May 12
FLL
Fort Lauderdale
EWR
New York
$83 Roundtrip, found 3 days ago
$83
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Sat, May 9 from Fort Lauderdale to New York, returning Tue, May 12, priced at $83 found 3 days ago

Top rated hotels for your Shelter Island vacation

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
18.43 mi from city center
$459 nightly
The price is $524 total per night
$524 total
Mar 22 - Mar 23
Total with taxes and fees
Located in Montauk, Gurney's Montauk Resort & Seawater Spa is by the ocean, a 3-minute drive from Hither Hills State Park and 7 minutes from Shadmoor State Park.
On private beach
Pool
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
20.31 mi from city center
$148 nightly
The price is $169 total per night
$169 total
Mar 8 - Mar 9
Total with taxes and fees
When you stay at Montauk Manor in Montauk, you'll be near the beach, within a 15-minute walk of The Hamptons Beaches and Shadmoor State Park.
Pool
Hot Tub
Montauk Blue Hotel

Montauk Blue Hotel

2 out of 5
108 South Emerson Avenue Montauk NY
20.67 mi from city center
Get rates
With a stay at Montauk Blue Hotel in Montauk (Downtown Montauk), you'll be steps from The Hamptons Beaches and South Edison Beach.
Pool
Hot Tub
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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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.