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.
Hotel 1200

Hotel 1200

3 out of 5
Save 100% on your flight
per person
May 19 - May 22
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
per person
May 24 - May 27
found 21 hours ago
Roundtrip non-stop 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
per person
May 8 - May 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Hotel 1080 Brooklyn

Hotel 1080 Brooklyn

3.5 out of 5
Save 100% on your flight
per person
Jun 1 - Jun 4
found 16 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
The Luxury Collection Hotel Manhattan Midtown

The Luxury Collection Hotel Manhattan Midtown

5 out of 5
Save 100% on your flight
per person
May 23 - May 26
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to New York (JFK)
The Carlyle, A Rosewood Hotel

The Carlyle, A Rosewood Hotel

5 out of 5
Save 100% on your flight
per person
May 24 - May 27
found 21 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to New York (JFK)
The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Save 100% on your flight
per person
May 24 - May 27
found 21 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to New York (JFK)
New York Marriott Downtown

New York Marriott Downtown

4 out of 5
Save 100% on your flight
per person
May 30 - Jun 2
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Night Hotel Broadway

Night Hotel Broadway

2.5 out of 5
Save 100% on your flight
per person
May 14 - May 17
found 8 hours ago
Roundtrip flight included
San Juan (SJU) to New York (JFK)
New York Marriott Marquis

New York Marriott Marquis

4.5 out of 5
Save 100% on your flight
per person
May 27 - May 30
found 1 hour ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
PUBLIC, an Ian Schrager hotel

PUBLIC, an Ian Schrager hotel

4 out of 5
per person
May 27 - May 30
found 1 hour ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
Arlo Williamsburg

Arlo Williamsburg

4 out of 5
Save 100% on your flight
per person
Jun 1 - Jun 4
found 16 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)

4-night Shelter Island vacations

Price found within the past 48 hours. Click for updated prices.
The George

The George

4 out of 5
Save 100% on your flight
per person
May 8 - May 12
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
per person
May 14 - May 18
found 8 hours ago
Roundtrip flight included
San Juan (SJU) to New York (JFK)
PUBLIC, an Ian Schrager hotel

PUBLIC, an Ian Schrager hotel

4 out of 5
Save 100% on your flight
per person
May 12 - May 16
found 5 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
Hotel St. James

Hotel St. James

2.5 out of 5
Save 100% on your flight
per person
May 24 - May 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Millennium Hotel Broadway Times Square

Millennium Hotel Broadway Times Square

4 out of 5
Save 100% on your flight
per person
May 12 - May 16
found 5 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
per person
Jun 1 - Jun 5
found 3 hours ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
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
per person
May 12 - May 16
found 5 hours ago
Roundtrip flight included
Dallas (DAL) 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
per person
May 12 - May 16
found 5 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
Ink 48 Hotel

Ink 48 Hotel

4.5 out of 5
Save 100% on your flight
per person
May 12 - May 16
found 5 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
New York Marriott Marquis

New York Marriott Marquis

4.5 out of 5
Save 100% on your flight
per person
May 12 - May 16
found 5 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
Hotel 32 32

Hotel 32 32

4 out of 5
Save 100% on your flight
per person
May 12 - May 16
found 5 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
per person
May 22 - May 26
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)

5-night Shelter Island vacations

Price found within the past 48 hours. Click for updated prices.
Pocono Mountain Villas by Exploria Resorts

Pocono Mountain Villas by Exploria Resorts

3.5 out of 5
per person
May 12 - May 17
found 8 hours ago
Roundtrip flight included
San Juan (SJU) to Newark Liberty Intl. Airport (EWR)
Peachtree Suites

Peachtree Suites

2.5 out of 5
Save 100% on your flight
per person
May 23 - May 28
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
La Quinta Inn & Suites by Wyndham Secaucus Meadowlands

La Quinta Inn & Suites by Wyndham Secaucus Meadowlands

3 out of 5
Save 100% on your flight
per person
May 26 - May 31
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
PUBLIC, an Ian Schrager hotel

PUBLIC, an Ian Schrager hotel

4 out of 5
Save 100% on your flight
per person
May 26 - May 31
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to New York (JFK)
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Save 100% on your flight
per person
May 14 - May 19
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Save 100% on your flight
per person
May 26 - May 31
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to New York (JFK)
Royalton New York

Royalton New York

4 out of 5
Save 100% on your flight
per person
May 29 - Jun 3
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
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
per person
May 26 - May 31
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to New York (JFK)
Hotel Beacon

Hotel Beacon

4 out of 5
Save 100% on your flight
per person
May 14 - May 19
found 6 hours ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Save 100% on your flight
per person
May 14 - May 19
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Millennium Hotel Broadway Times Square

Millennium Hotel Broadway Times Square

4 out of 5
Save 100% on your flight
per person
May 26 - May 31
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to New York (JFK)
Hilton Garden Inn Edison/Raritan Center

Hilton Garden Inn Edison/Raritan Center

3 out of 5
Save 100% on your flight
per person
May 23 - May 28
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)

6-7 night Shelter Island vacations

Price found within the past 48 hours. Click for updated prices.
Hyatt Place Fort Lee / George Washington Bridge

Hyatt Place Fort Lee / George Washington Bridge

3 out of 5
Save 100% on your flight
per person
May 13 - May 19
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
Park Lane New York

Park Lane New York

5 out of 5
Save 100% on your flight
per person
May 23 - May 30
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
per person
May 14 - May 20
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
La Quinta Inn & Suites by Wyndham Secaucus Meadowlands

La Quinta Inn & Suites by Wyndham Secaucus Meadowlands

3 out of 5
Save 100% on your flight
per person
May 22 - May 29
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
PUBLIC, an Ian Schrager hotel

PUBLIC, an Ian Schrager hotel

4 out of 5
Save 100% on your flight
per person
May 14 - May 20
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
per person
May 14 - May 20
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Hotel 27 by LuxUrban

Hotel 27 by LuxUrban

2.5 out of 5
Save 100% on your flight
per person
May 14 - May 20
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
The Herald by LuxUrban

The Herald by LuxUrban

2.5 out of 5
Save 100% on your flight
per person
May 14 - May 20
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Millennium Hotel Broadway Times Square

Millennium Hotel Broadway Times Square

4 out of 5
Save 100% on your flight
per person
May 14 - May 20
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Save 100% on your flight
per person
May 23 - May 30
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
per person
May 21 - May 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Save 100% on your flight
per person
May 14 - May 20
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)

Flight deals to Shelter Island

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

Mon, Apr 14 - Tue, Apr 22
MIA
Miami
EWR
New York
$65 Roundtrip, found 6 days ago
$65
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Mon, Apr 14 from Miami to New York, returning Tue, Apr 22, priced at $65 found 6 days ago
Wed, May 14 - Mon, May 19
MIA
Miami
LGA
New York
$68 Roundtrip, found 1 day ago
$68
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, May 14 from Miami to New York, returning Mon, May 19, priced at $68 found 1 day ago
Wed, Apr 30 - Mon, May 5
MIA
Miami
JFK
New York
$68 Roundtrip, found 1 day ago
$68
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Apr 30 from Miami to New York, returning Mon, May 5, priced at $68 found 1 day ago

Top rated hotels for your Shelter Island vacation

Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St., Montauk, NY
20.31 mi from city center
The price is $208 per night
$208
includes taxes & fees
$182 per night
Apr 15 - Apr 16
When you stay at Montauk Manor in Montauk, you'll be near the beach, within a 15-minute drive of The Hamptons Beaches and Montauk Point.
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
Reserve now, pay when you stay
15.48 mi from city center
The price is $91 per night
$91
includes taxes & fees
$79 per night
Apr 7 - Apr 8
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.
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
The price is $246 per night
$246
includes taxes & fees
$214 per night
Apr 7 - Apr 8
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.
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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.