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.
Sheraton Parsippany Hotel

Sheraton Parsippany Hotel

4 out of 5
Save 100% on your flight
Price was $600, price is now $383 per person
$383
per person
Apr 16 - Apr 19
found 3 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Newark Liberty Intl. Airport (EWR)
Park Lane New York

Park Lane New York

5 out of 5
Price was $1,105, price is now $689 per person
$689
per person
Apr 22 - Apr 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 $1,461, price is now $965 per person
$965
per person
May 4 - May 7
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 $796, price is now $537 per person
$537
per person
May 5 - May 8
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Pestana Park Avenue

Pestana Park Avenue

4 out of 5
Save 100% on your flight
Price was $1,204, price is now $845 per person
$845
per person
May 4 - May 7
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 $1,087, price is now $772 per person
$772
per person
May 7 - May 10
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) 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 $1,308, price is now $931 per person
$931
per person
May 7 - May 10
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) 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 $2,106, price is now $1,505 per person
$1,505
per person
May 4 - May 7
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Price was $922, price is now $672 per person
$672
per person
May 7 - May 10
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to Newark Liberty Intl. Airport (EWR)
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Price was $1,311, price is now $958 per person
$958
per person
Apr 13 - Apr 16
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Newark Liberty Intl. Airport (EWR)
Beachwalk at Sea Bright

Beachwalk at Sea Bright

2.5 out of 5
Save 100% on your flight
Price was $707, price is now $527 per person
$527
per person
Apr 30 - May 3
found 20 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to New York (JFK)
Library Hotel by Library Hotel Collection

Library Hotel by Library Hotel Collection

4 out of 5
Save 100% on your flight
Price was $901, price is now $673 per person
$673
per person
May 7 - May 10
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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 $818, price is now $455 per person
$455
per person
May 6 - May 10
found 13 hours ago
Roundtrip flight included
Dallas (DAL) to Newark Liberty Intl. Airport (EWR)
Hotel St. James

Hotel St. James

2.5 out of 5
Save 100% on your flight
Price was $1,172, price is now $637 per person
$637
per person
May 6 - May 10
found 13 hours ago
Roundtrip flight included
Dallas (DAL) to Newark Liberty Intl. Airport (EWR)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $2,702, price is now $1,539 per person
$1,539
per person
Apr 17 - Apr 21
found 15 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Newark Liberty Intl. Airport (EWR)
Park Lane New York

Park Lane New York

5 out of 5
Save 100% on your flight
Price was $1,791, price is now $1,123 per person
$1,123
per person
May 4 - May 8
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 $2,137, price is now $1,366 per person
$1,366
per person
Apr 30 - May 4
found 23 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) 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 $809, price is now $522 per person
$522
per person
May 6 - May 10
found 13 hours ago
Roundtrip flight included
Dallas (DAL) 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 $1,446, price is now $940 per person
$940
per person
May 6 - May 10
found 13 hours ago
Roundtrip flight included
Dallas (DAL) to Newark Liberty Intl. Airport (EWR)
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Price was $1,470, price is now $956 per person
$956
per person
May 1 - May 5
found 1 day ago
Roundtrip non-stop 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 $1,044, price is now $688 per person
$688
per person
Apr 30 - May 4
found 7 hours ago
Roundtrip flight included
Dallas (DFW) 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 $958, price is now $644 per person
$644
per person
May 6 - May 10
found 13 hours ago
Roundtrip flight included
Dallas (DAL) to Newark Liberty Intl. Airport (EWR)
Nine Orchard

Nine Orchard

5 out of 5
Save 100% on your flight
Price was $1,720, price is now $1,166 per person
$1,166
per person
Apr 17 - Apr 21
found 15 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Newark Liberty Intl. Airport (EWR)
Hilton Club The Quin New York

Hilton Club The Quin New York

5 out of 5
Save 100% on your flight
Price was $2,001, price is now $1,359 per person
$1,359
per person
Apr 30 - May 4
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)

5-night Shelter Island vacations

Price found within the past 48 hours. Click for updated prices.
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Save 100% on your flight
Price was $1,016, price is now $687 per person
$687
per person
May 5 - May 10
found 17 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) 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 $1,210, price is now $714 per person
$714
per person
Apr 26 - May 1
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 $1,269, price is now $794 per person
$794
per person
Apr 27 - May 2
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Newark Liberty Intl. Airport (EWR)
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Save 100% on your flight
Price was $1,602, price is now $1,067 per person
$1,067
per person
Apr 26 - May 1
found 1 day 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 $1,862, price is now $1,245 per person
$1,245
per person
Apr 26 - May 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
The Westin New York Grand Central

The Westin New York Grand Central

4.5 out of 5
Save 100% on your flight
Price was $1,594, price is now $1,073 per person
$1,073
per person
Apr 26 - May 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Newark Liberty International Airport Marriott

Newark Liberty International Airport Marriott

4 out of 5
Save 100% on your flight
Price was $1,143, price is now $770 per person
$770
per person
Apr 15 - Apr 20
found 18 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Newark Liberty Intl. Airport (EWR)
The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Save 100% on your flight
Price was $3,033, price is now $2,043 per person
$2,043
per person
Apr 26 - May 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 $1,856, price is now $1,256 per person
$1,256
per person
Apr 27 - May 2
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Newark Liberty Intl. Airport (EWR)
Hotel Seville Nomad, in the Unbound Collection by Hyatt

Hotel Seville Nomad, in the Unbound Collection by Hyatt

4.5 out of 5
Save 100% on your flight
Price was $1,351, price is now $915 per person
$915
per person
Apr 23 - Apr 28
found 1 day ago
Roundtrip 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 $1,463, price is now $1,001 per person
$1,001
per person
Apr 26 - May 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Margaritaville Resort Times Square

Margaritaville Resort Times Square

4 out of 5
Save 100% on your flight
Price was $1,350, price is now $924 per person
$924
per person
Apr 27 - May 2
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Newark Liberty Intl. Airport (EWR)

6-7 night Shelter Island vacations

Price found within the past 48 hours. Click for updated prices.
Nova Hotel Brooklyn

Nova Hotel Brooklyn

3 out of 5
Price was $1,116, price is now $745 per person
$745
per person
Apr 29 - May 6
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Price was $3,852, price is now $2,203 per person
$2,203
per person
Apr 29 - May 6
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $5,110, price is now $2,978 per person
$2,978
per person
Apr 29 - May 6
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Price was $4,571, price is now $2,757 per person
$2,757
per person
Apr 29 - May 6
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
The William Vale

The William Vale

5 out of 5
Price was $3,157, price is now $1,912 per person
$1,912
per person
Apr 29 - May 6
found 11 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
Price was $1,827, price is now $1,135 per person
$1,135
per person
Apr 29 - May 6
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Price was $3,261, price is now $2,028 per person
$2,028
per person
Apr 29 - May 6
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
The Plaza - A Fairmont Managed Hotel

The Plaza - A Fairmont Managed Hotel

5 out of 5
Price was $7,271, price is now $4,774 per person
$4,774
per person
Apr 29 - May 6
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
OYO Times Square

OYO Times Square

4 out of 5
Price was $1,491, price is now $991 per person
$991
per person
Apr 29 - May 6
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Ace Hotel New York

Ace Hotel New York

4 out of 5
Price was $1,604, price is now $1,074 per person
$1,074
per person
Apr 29 - May 6
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Park Central Hotel New York

Park Central Hotel New York

4 out of 5
Save 100% on your flight
Price was $1,893, price is now $1,271 per person
$1,271
per person
Apr 13 - Apr 19
found 22 hours ago
Roundtrip flight included
Dallas (DAL) 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 $2,264, price is now $1,521 per person
$1,521
per person
Apr 13 - Apr 19
found 22 hours ago
Roundtrip flight included
Dallas (DAL) 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.

Wed, Apr 1 - Wed, Apr 8
ATL
Atlanta
LGA
New York
$56 Roundtrip, found 3 days ago
$56
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Apr 1 from Atlanta to New York, returning Wed, Apr 8, priced at $56 found 3 days ago
Tue, Mar 31 - Tue, Apr 7
ATL
Atlanta
EWR
New York
$56 Roundtrip, found 2 days ago
$56
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Mar 31 from Atlanta to New York, returning Tue, Apr 7, priced at $56 found 2 days ago
Tue, Mar 24 - Tue, Apr 14
ATL
Atlanta
JFK
New York
$58 Roundtrip, found 6 days ago
$58
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Tue, Mar 24 from Atlanta to New York, returning Tue, Apr 14, priced at $58 found 6 days ago
Wed, May 6 - Wed, May 13
MCO
Orlando
LGA
New York
$70 Roundtrip, found 6 days ago
$70
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, May 6 from Orlando to New York, returning Wed, May 13, priced at $70 found 6 days ago
Sat, May 2 - Wed, May 6
MCO
Orlando
EWR
New York
$88 Roundtrip, found 5 days ago
$88
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, May 2 from Orlando to New York, returning Wed, May 6, priced at $88 found 5 days ago
Wed, Apr 1 - Wed, Apr 8
MIA
Miami
LGA
New York
$90 Roundtrip, found 1 hour ago
$90
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Wed, Apr 1 from Miami to New York, returning Wed, Apr 8, priced at $90 found 1 hour 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 25 - Mar 26
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.
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 15 - Mar 16
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.
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Free Cancellation
Reserve now, pay when you stay
15.59 mi from city center
$204 nightly
The price is $235 total per night
$235 total
Apr 1 - Apr 2
Total with taxes and fees
With a stay at Water's Edge Resort & Spa in Westbrook (Westbrook Center), you'll be a 4-minute drive from Tanger Outlets and 8 minutes from Clinton Crossing Premium Outlets.
Don't see what you're looking for?
See all available properties in Shelter Island
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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 Picks

^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.