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.
Home2 Suites by Hilton Newark Airport

Home2 Suites by Hilton Newark Airport

3 out of 5
Price was $404, price is now $290 per person
$290
per person
Apr 25 - Apr 28
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 $1,310, price is now $784 per person
$784
per person
Apr 16 - Apr 19
found 21 hours ago
Roundtrip flight included
Burbank (BUR) 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 $1,506, price is now $932 per person
$932
per person
Apr 30 - May 3
found 1 day 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 $2,304, price is now $1,507 per person
$1,507
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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 $1,304, price is now $857 per person
$857
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Placemakr Wall Street

Placemakr Wall Street

4 out of 5
Save 100% on your flight
Price was $924, price is now $633 per person
$633
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
The William Vale

The William Vale

5 out of 5
Price was $1,460, price is now $1,012 per person
$1,012
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Save 100% on your flight
Price was $1,119, price is now $786 per person
$786
per person
Apr 23 - Apr 26
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 $1,398, price is now $988 per person
$988
per person
Apr 16 - Apr 19
found 21 hours ago
Roundtrip flight included
Burbank (BUR) to Newark Liberty Intl. Airport (EWR)
Hyatt House Jersey City

Hyatt House Jersey City

3.5 out of 5
Save 100% on your flight
Price was $660, price is now $468 per person
$468
per person
Apr 20 - Apr 23
just found
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Library Hotel by Library Hotel Collection

Library Hotel by Library Hotel Collection

4 out of 5
Save 100% on your flight
Price was $892, price is now $638 per person
$638
per person
Apr 30 - May 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Dharma Home Suites Hoboken at Novia

Dharma Home Suites Hoboken at Novia

4 out of 5
Save 100% on your flight
Price was $772, price is now $554 per person
$554
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)

4-night Shelter Island vacations

Price found within the past 48 hours. Click for updated prices.
Sound View Greenport

Sound View Greenport

4 out of 5
Save 100% on your flight
Price was $646, price is now $422 per person
$422
per person
Apr 14 - Apr 18
found 13 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Topping Rose House

Topping Rose House

4.5 out of 5
Price was $1,672, price is now $916 per person
$916
per person
Apr 14 - Apr 18
found 13 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Save 100% on your flight
Price was $2,435, price is now $1,498 per person
$1,498
per person
Apr 20 - Apr 24
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 $979, price is now $620 per person
$620
per person
Apr 20 - Apr 24
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 $1,498, price is now $955 per person
$955
per person
Apr 20 - Apr 24
found 1 day ago
Roundtrip 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 $1,119, price is now $726 per person
$726
per person
Apr 9 - Apr 13
found 10 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
The Maidstone

The Maidstone

4 out of 5
Save 100% on your flight
Price was $1,435, price is now $936 per person
$936
per person
Apr 14 - Apr 18
found 13 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Save 100% on your flight
Price was $2,250, price is now $1,473 per person
$1,473
per person
Apr 28 - May 2
found 1 day 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 $833, price is now $546 per person
$546
per person
Apr 20 - Apr 24
found 1 day 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 $819, price is now $545 per person
$545
per person
Apr 24 - Apr 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Holiday Inn Express New York - Manhattan West Side by IHG

Holiday Inn Express New York - Manhattan West Side by IHG

2.5 out of 5
Price was $930, price is now $630 per person
$630
per person
Apr 24 - Apr 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Interfaith 21

Interfaith 21

2 out of 5
Save 100% on your flight
Price was $838, price is now $574 per person
$574
per person
Apr 17 - Apr 21
found 3 hours 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.
Nova Hotel Brooklyn

Nova Hotel Brooklyn

3 out of 5
Save 100% on your flight
Price was $808, price is now $578 per person
$578
per person
Apr 19 - Apr 24
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
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 $1,051, price is now $677 per person
$677
per person
Apr 19 - Apr 24
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Save 100% on your flight
Price was $1,817, price is now $1,184 per person
$1,184
per person
Apr 22 - Apr 27
found 5 hours ago
Roundtrip flight included
Burbank (BUR) 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 $2,115, price is now $1,382 per person
$1,382
per person
Apr 22 - Apr 27
found 5 hours ago
Roundtrip flight included
Burbank (BUR) to Newark Liberty Intl. Airport (EWR)
The Maidstone

The Maidstone

4 out of 5
Save 100% on your flight
Price was $2,594, price is now $1,734 per person
$1,734
per person
Apr 18 - Apr 23
found 3 hours ago
Roundtrip flight included
Orange County (SNA) to New York (JFK)
Holiday Inn Express New York - Manhattan West Side by IHG

Holiday Inn Express New York - Manhattan West Side by IHG

2.5 out of 5
Save 100% on your flight
Price was $1,308, price is now $894 per person
$894
per person
Apr 19 - Apr 24
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Sound View Greenport

Sound View Greenport

4 out of 5
Save 100% on your flight
Price was $1,154, price is now $795 per person
$795
per person
Apr 18 - Apr 23
found 3 hours ago
Roundtrip flight included
Orange County (SNA) to New York (JFK)
Harpoon House

Harpoon House

3 out of 5
Save 100% on your flight
Price was $1,232, price is now $857 per person
$857
per person
Apr 18 - Apr 23
found 3 hours ago
Roundtrip flight included
Orange County (SNA) to New York (JFK)
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 $1,037, price is now $729 per person
$729
per person
Apr 19 - Apr 24
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Topping Rose House

Topping Rose House

4.5 out of 5
Save 100% on your flight
Price was $2,358, price is now $1,705 per person
$1,705
per person
Apr 18 - Apr 23
found 3 hours ago
Roundtrip flight included
Orange County (SNA) to New York (JFK)
The William Vale

The William Vale

5 out of 5
Save 100% on your flight
Price was $1,932, price is now $1,397 per person
$1,397
per person
Apr 4 - Apr 9
found 1 day ago
Roundtrip flight included
Los Angeles (QLA) to New York (JFK)

6-7 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
Price was $1,174, price is now $585 per person
$585
per person
Apr 21 - Apr 27
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
Price was $1,436, price is now $729 per person
$729
per person
Apr 21 - Apr 27
found 1 day ago
Roundtrip 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 $2,096, price is now $1,218 per person
$1,218
per person
Apr 21 - Apr 27
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 $1,462, price is now $871 per person
$871
per person
Apr 21 - Apr 27
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
Price was $1,997, price is now $1,217 per person
$1,217
per person
Apr 22 - Apr 28
just found
Roundtrip 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 $1,202, price is now $745 per person
$745
per person
Apr 21 - Apr 27
found 1 day 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 $1,195, price is now $747 per person
$747
per person
Apr 21 - Apr 27
found 1 day 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 $1,409, price is now $883 per person
$883
per person
Apr 21 - Apr 27
found 1 day 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 $1,298, price is now $817 per person
$817
per person
Apr 21 - Apr 27
found 1 day ago
Roundtrip 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 $1,555, price is now $1,006 per person
$1,006
per person
Apr 21 - Apr 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Holiday Inn Express New York - Manhattan West Side by IHG

Holiday Inn Express New York - Manhattan West Side by IHG

2.5 out of 5
Save 100% on your flight
Price was $1,594, price is now $1,035 per person
$1,035
per person
Apr 21 - Apr 27
found 1 day 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 $1,453, price is now $944 per person
$944
per person
Apr 21 - Apr 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 15 - Sat, May 16
ATL
Atlanta
LGA
New York
$56 Roundtrip, found 4 hours ago
$56
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Fri, May 15 from Atlanta to New York, returning Sat, May 16, priced at $56 found 4 hours ago
Mon, Mar 23 - Tue, Mar 24
ATL
Atlanta
JFK
New York
$56 Roundtrip, found 1 day ago
$56
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Mar 23 from Atlanta to New York, returning Tue, Mar 24, priced at $56 found 1 day ago
Wed, Apr 22 - Wed, Apr 22
MCO
Orlando
LGA
New York
$56 Roundtrip, found 5 days ago
$56
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, Apr 22 from Orlando to New York, returning Wed, Apr 22, priced at $56 found 5 days ago
Fri, May 8 - Sat, May 9
ATL
Atlanta
EWR
New York
$56 Roundtrip, found 5 hours ago
$56
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Fri, May 8 from Atlanta to New York, returning Sat, May 9, priced at $56 found 5 hours ago
Sat, Jun 6 - Tue, Jun 9
MCO
Orlando
EWR
New York
$82 Roundtrip, found 3 days ago
$82
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Jun 6 from Orlando to New York, returning Tue, Jun 9, priced at $82 found 3 days ago
Sat, May 9 - Tue, May 12
FLL
Fort Lauderdale
EWR
New York
$83 Roundtrip, found 9 hours ago
$83
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Sat, May 9 from Fort Lauderdale to New York, returning Tue, May 12, priced at $83 found 9 hours 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 17 - Mar 18
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 5 - Mar 6
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.
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Free Cancellation
15.48 mi from city center
$104 nightly
The price is $120 total per night
$120 total
Mar 5 - Mar 6
Total with taxes and fees
Located in Old Saybrook (Saybrook Manor), Pier Blue Inn Old Saybrook - Essex is within a 5-minute drive of Chalker Beach and Crystal Lake Town Park.
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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.