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.
Sound View Greenport

Sound View Greenport

4 out of 5
Save 100% on your flight
Price was $540, price is now $374 per person
$374
per person
Apr 15 - Apr 18
found 1 hour 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 $1,280, price is now $744 per person
$744
per person
Apr 15 - Apr 18
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
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 23 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)
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Price was $1,306, price is now $848 per person
$848
per person
Apr 3 - Apr 6
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)
Harpoon House

Harpoon House

3 out of 5
Save 100% on your flight
Price was $624, price is now $413 per person
$413
per person
Apr 15 - Apr 18
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
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 23 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
found 2 hours 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 16 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 16 hours 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 $1,541, price is now $977 per person
$977
per person
Apr 28 - May 2
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 $1,489, price is now $946 per person
$946
per person
Apr 28 - May 2
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 12 hours 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 $1,347, price is now $876 per person
$876
per person
Apr 11 - Apr 15
found 1 day 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 16 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)
Hotel St. James

Hotel St. James

2.5 out of 5
Save 100% on your flight
Price was $1,032, price is now $699 per person
$699
per person
Apr 11 - Apr 15
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 $840, price is now $570 per person
$570
per person
Apr 11 - Apr 15
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 6 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.
The Dutch Hotel Long Island City, Sonder by Marriott Bonvoy

The Dutch Hotel Long Island City, Sonder by Marriott Bonvoy

3.5 out of 5
Save 100% on your flight
Price was $1,072, price is now $785 per person
$785
per person
Apr 25 - Apr 30
found 2 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 $1,817, price is now $1,184 per person
$1,184
per person
Apr 22 - Apr 27
found 8 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 8 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 5 hours ago
Roundtrip flight included
Orange County (SNA) to New York (JFK)
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 5 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 5 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)
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 5 hours ago
Roundtrip flight included
Orange County (SNA) to New York (JFK)
The Wall Street Hotel

The Wall Street Hotel

5 out of 5
Save 100% on your flight
Price was $2,004, price is now $1,459 per person
$1,459
per person
Apr 21 - Apr 26
just found
Roundtrip flight included
San Francisco (SFO) to Newark Liberty Intl. Airport (EWR)
The Renwick

The Renwick

4 out of 5
Save 100% on your flight
Price was $1,207, price is now $886 per person
$886
per person
Apr 22 - Apr 27
found 8 hours ago
Roundtrip flight included
Burbank (BUR) to Newark Liberty Intl. Airport (EWR)
The Ritz-Carlton New York, Central Park

The Ritz-Carlton New York, Central Park

5 out of 5
Save 100% on your flight
Price was $3,811, price is now $2,827 per person
$2,827
per person
Apr 22 - Apr 27
found 8 hours ago
Roundtrip flight included
Burbank (BUR) to Newark Liberty Intl. Airport (EWR)

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
found 2 hours ago
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 6 hours ago
$56
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Fri, May 15 from Atlanta to New York, returning Sat, May 16, priced at $56 found 6 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 7 hours ago
$56
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Fri, May 8 from Atlanta to New York, returning Sat, May 9, priced at $56 found 7 hours ago
Sat, Jun 6 - Tue, Jun 9
MCO
Orlando
EWR
New York
$82 Roundtrip, found 4 days ago
$82
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Jun 6 from Orlando to New York, returning Tue, Jun 9, priced at $82 found 4 days ago
Sat, May 9 - Tue, May 12
FLL
Fort Lauderdale
EWR
New York
$83 Roundtrip, found 11 hours ago
$83
Roundtrip
found 11 hours ago
Select Spirit Airlines flight, departing Sat, May 9 from Fort Lauderdale to New York, returning Tue, May 12, priced at $83 found 11 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.
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 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.
Pool
Hot Tub
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.
Pet friendly
Parking included
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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.