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.
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Save 100% on your flight
Price was $454, price is now $312 per person
$312
per person
Mar 8 - Mar 11
found 17 hours ago
Roundtrip flight included
Chicago (ORD) 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
Price was $803, price is now $494 per person
$494
per person
Feb 27 - Mar 2
found 20 hours ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Save 100% on your flight
Price was $702, price is now $432 per person
$432
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to New York (JFK)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $1,673, price is now $1,073 per person
$1,073
per person
Feb 26 - Mar 1
found 16 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Oheka Castle Hotel & Estate

Oheka Castle Hotel & Estate

3.5 out of 5
Save 100% on your flight
Price was $804, price is now $520 per person
$520
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
CODA Williamsburg

CODA Williamsburg

4 out of 5
Save 100% on your flight
Price was $666, price is now $432 per person
$432
per person
Feb 26 - Mar 1
found 16 hours 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
Price was $890, price is now $579 per person
$579
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to New York (JFK)
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Price was $1,258, price is now $824 per person
$824
per person
Mar 9 - Mar 12
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Pendry Natirar

Pendry Natirar

5 out of 5
Save 100% on your flight
Price was $1,963, price is now $1,289 per person
$1,289
per person
Mar 12 - Mar 15
found 14 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Newark Liberty Intl. Airport (EWR)
American Hotel

American Hotel

3.5 out of 5
Save 100% on your flight
Price was $503, price is now $338 per person
$338
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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 $821, price is now $563 per person
$563
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to New York (JFK)
The High Line Hotel

The High Line Hotel

4 out of 5
Save 100% on your flight
Price was $953, price is now $656 per person
$656
per person
Feb 15 - Feb 18
found 1 day ago
Roundtrip flight included
Detroit (DTW) to New York (JFK)

4-night Shelter Island vacations

Price found within the past 48 hours. Click for updated prices.
Harmony Suites

Harmony Suites

3 out of 5
Save 100% on your flight
Price was $404, price is now $266 per person
$266
per person
Feb 16 - Feb 20
found 15 hours ago
Roundtrip flight included
Detroit (DTW) 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 $1,570, price is now $961 per person
$961
per person
Mar 6 - Mar 10
found 23 hours ago
Roundtrip flight included
Dallas (DAL) 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
Price was $1,100, price is now $740 per person
$740
per person
Feb 19 - Feb 23
found 21 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
Pendry Natirar

Pendry Natirar

5 out of 5
Save 100% on your flight
Price was $2,247, price is now $1,513 per person
$1,513
per person
Mar 5 - Mar 9
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 $1,038, price is now $707 per person
$707
per person
Feb 19 - Feb 23
found 21 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Save 100% on your flight
Price was $1,958, price is now $1,358 per person
$1,358
per person
Feb 25 - Mar 1
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Save 100% on your flight
Price was $1,605, price is now $1,114 per person
$1,114
per person
Mar 6 - Mar 10
found 22 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
Holiday Inn Hasbrouck Heights-Meadowlands by IHG

Holiday Inn Hasbrouck Heights-Meadowlands by IHG

3 out of 5
Save 100% on your flight
Price was $499, price is now $348 per person
$348
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Newark Liberty Intl. Airport (EWR)
The Asbury Hotel

The Asbury Hotel

3.5 out of 5
Save 100% on your flight
Price was $687, price is now $479 per person
$479
per person
Mar 13 - Mar 17
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 $802, price is now $560 per person
$560
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip flight included
Detroit (DTW) to New York (JFK)
Outsite Chelsea

Outsite Chelsea

2 out of 5
Price was $722, price is now $504 per person
$504
per person
Mar 12 - Mar 16
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Park Lane New York

Park Lane New York

5 out of 5
Price was $1,162, price is now $812 per person
$812
per person
Mar 12 - Mar 16
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)

5-night Shelter Island vacations

Price found within the past 48 hours. Click for updated prices.
Best Western Plus Meadowlands

Best Western Plus Meadowlands

3.5 out of 5
Save 100% on your flight
Price was $510, price is now $335 per person
$335
per person
Feb 27 - Mar 4
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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 $1,056, price is now $553 per person
$553
per person
Mar 9 - Mar 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
The Lexington Hotel, Autograph Collection

The Lexington Hotel, Autograph Collection

4 out of 5
Save 100% on your flight
Price was $1,216, price is now $673 per person
$673
per person
Mar 9 - Mar 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Hotel St. James

Hotel St. James

2.5 out of 5
Save 100% on your flight
Price was $1,025, price is now $573 per person
$573
per person
Mar 9 - Mar 14
found 1 day ago
Roundtrip 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
Price was $1,211, price is now $757 per person
$757
per person
Feb 15 - Feb 20
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
Price was $1,793, price is now $1,125 per person
$1,125
per person
Mar 5 - Mar 10
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to New York (JFK)
Harmony Suites

Harmony Suites

3 out of 5
Save 100% on your flight
Price was $556, price is now $352 per person
$352
per person
Feb 27 - Mar 4
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Newark Liberty Intl. Airport (EWR)
Arthouse Hotel New York City

Arthouse Hotel New York City

4 out of 5
Save 100% on your flight
Price was $822, price is now $538 per person
$538
per person
Mar 9 - Mar 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Interfaith 21

Interfaith 21

2 out of 5
Save 100% on your flight
Price was $1,017, price is now $673 per person
$673
per person
Mar 9 - Mar 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Millennium Hilton New York One UN Plaza

Millennium Hilton New York One UN Plaza

4 out of 5
Save 100% on your flight
Price was $1,874, price is now $1,257 per person
$1,257
per person
Mar 9 - Mar 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Radio Hotel

Radio Hotel

4 out of 5
Save 100% on your flight
Price was $604, price is now $406 per person
$406
per person
Feb 27 - Mar 4
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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
Save 100% on your flight
Price was $1,027, price is now $494 per person
$494
per person
Feb 23 - Mar 1
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
Price was $1,340, price is now $734 per person
$734
per person
Feb 23 - Mar 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Park Lane New York

Park Lane New York

5 out of 5
Save 100% on your flight
Price was $1,939, price is now $1,087 per person
$1,087
per person
Feb 15 - Feb 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Hotel St. James

Hotel St. James

2.5 out of 5
Save 100% on your flight
Price was $891, price is now $508 per person
$508
per person
Feb 23 - Mar 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Pendry Natirar

Pendry Natirar

5 out of 5
Save 100% on your flight
Price was $3,204, price is now $1,875 per person
$1,875
per person
Feb 23 - Mar 1
found 12 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
The Lexington Hotel, Autograph Collection

The Lexington Hotel, Autograph Collection

4 out of 5
Save 100% on your flight
Price was $1,138, price is now $669 per person
$669
per person
Feb 23 - Mar 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Save 100% on your flight
Price was $933, price is now $549 per person
$549
per person
Feb 23 - Mar 1
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 $1,169, price is now $720 per person
$720
per person
Feb 23 - Mar 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
CODA Williamsburg

CODA Williamsburg

4 out of 5
Price was $1,187, price is now $735 per person
$735
per person
Feb 19 - Feb 25
found 10 hours ago
Roundtrip flight included
San Juan (SJU) 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
Price was $1,669, price is now $1,043 per person
$1,043
per person
Feb 15 - Feb 22
found 1 day ago
Roundtrip 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 $2,206, price is now $1,427 per person
$1,427
per person
Feb 15 - Feb 22
found 1 day ago
Roundtrip 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
Price was $1,823, price is now $1,193 per person
$1,193
per person
Mar 11 - Mar 17
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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.

Wed, Feb 4 - Sat, Feb 7
MCO
Orlando
LGA
New York
$50 Roundtrip, found 3 days ago
$50
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Wed, Feb 4 from Orlando to New York, returning Sat, Feb 7, priced at $50 found 3 days ago
Sat, Feb 14 - Wed, Feb 18
MCO
Orlando
EWR
New York
$54 Roundtrip, found 2 days ago
$54
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sat, Feb 14 from Orlando to New York, returning Wed, Feb 18, priced at $54 found 2 days ago
Tue, Feb 10 - Wed, Feb 25
MIA
Miami
EWR
New York
$55 Roundtrip, found 1 day ago
$55
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Feb 10 from Miami to New York, returning Wed, Feb 25, priced at $55 found 1 day 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
$337 nightly
The price is $386 total per night
$386 total
Jan 19 - Jan 20
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
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
$244 nightly
The price is $281 total per night
$281 total
Jan 19 - Jan 20
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.
On private beach
Pool
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.