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.
Off Soho Suites Hotel

Off Soho Suites Hotel

2 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)
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Save 100% on your flight
per person
Apr 18 - Apr 21
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
per person
Apr 17 - Apr 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 8 - May 11
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
per person
May 8 - May 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
The Manhattan at Times Square Hotel

The Manhattan at Times Square Hotel

4 out of 5
Save 100% on your flight
per person
Apr 29 - May 2
found 1 day ago
Roundtrip flight included
Detroit (DTW) to New York (JFK)
The Blakely by LuxUrban

The Blakely by LuxUrban

2.5 out of 5
Save 100% on your flight
per person
May 10 - May 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 1 - May 4
found 21 hours ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
Condor Brooklyn

Condor Brooklyn

3.5 out of 5
Save 100% on your flight
per person
Apr 24 - Apr 27
found 3 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Beachwalk at Sea Bright

Beachwalk at Sea Bright

2.5 out of 5
Save 100% on your flight
per person
May 7 - May 10
found 1 day ago
Roundtrip flight included
Detroit (DTW) to New York (NYC)
Hilton Garden Inn New York/Manhattan-Chelsea

Hilton Garden Inn New York/Manhattan-Chelsea

3 out of 5
Save 100% on your flight
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to New York (JFK)
The Gotham Hotel

The Gotham Hotel

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)

4-night Shelter Island vacations

Price found within the past 48 hours. Click for updated prices.
Club Quarters, Times Square - Midtown

Club Quarters, Times Square - Midtown

4 out of 5
Save 100% on your flight
per person
Apr 25 - Apr 29
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
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip 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
Apr 23 - Apr 27
found 1 day 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 2 - May 6
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to New York (JFK)
Dream Downtown, by Hyatt

Dream Downtown, by Hyatt

4.5 out of 5
Save 100% on your flight
per person
Apr 23 - Apr 27
found 1 day 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
per person
May 2 - May 6
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) 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 2 - May 6
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to New York (JFK)
Moxy Brooklyn Williamsburg

Moxy Brooklyn Williamsburg

4 out of 5
Save 100% on your flight
per person
May 2 - May 6
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) 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 4 - May 8
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Concorde Hotel New York

Concorde Hotel New York

4 out of 5
Save 100% on your flight
per person
May 4 - May 8
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
The Gardens Sonesta ES Suites New York

The Gardens Sonesta ES Suites New York

3 out of 5
Save 100% on your flight
per person
Apr 19 - Apr 23
found 19 hours ago
Roundtrip flight included
Indianapolis (IND) to New York (JFK)
The Plaza - A Fairmont Managed Hotel

The Plaza - A Fairmont Managed Hotel

5 out of 5
Save 100% on your flight
per person
May 2 - May 6
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to New York (JFK)

5-night Shelter Island vacations

Price found within the past 48 hours. Click for updated prices.
Red Roof Inn PLUS+ Long Island - Garden City

Red Roof Inn PLUS+ Long Island - Garden City

2.5 out of 5
per person
Apr 18 - Apr 23
found 1 day 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
Apr 30 - May 5
found 6 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (JFK)
Moxy Brooklyn Williamsburg

Moxy Brooklyn Williamsburg

4 out of 5
Save 100% on your flight
per person
Apr 30 - May 5
found 6 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (JFK)
The Manhattan at Times Square Hotel

The Manhattan at Times Square Hotel

4 out of 5
Save 100% on your flight
per person
Apr 30 - May 5
found 6 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (JFK)
Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
per person
Apr 18 - Apr 23
found 1 day ago
Roundtrip 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
per person
Apr 18 - Apr 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Club Quarters, Times Square - Midtown

Club Quarters, Times Square - Midtown

4 out of 5
Save 100% on your flight
per person
Apr 25 - Apr 30
just found
Roundtrip flight included
Indianapolis (IND) 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
Apr 13 - Apr 18
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
Save 100% on your flight
per person
Apr 29 - May 4
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to New York (JFK)
Condor Brooklyn

Condor Brooklyn

3.5 out of 5
Save 100% on your flight
per person
Apr 25 - Apr 30
just found
Roundtrip flight included
Indianapolis (IND) to New York (JFK)
The Washington by LuxUrban

The Washington by LuxUrban

3 out of 5
Save 100% on your flight
per person
Apr 29 - May 4
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to New York (JFK)
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Save 100% on your flight
per person
Apr 13 - Apr 18
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)

6-7 night Shelter Island vacations

Price found within the past 48 hours. Click for updated prices.
East Norwich Inn

East Norwich Inn

2.5 out of 5
Save 100% on your flight
per person
Apr 13 - Apr 19
found 17 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) 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
Apr 18 - Apr 24
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to New York (JFK)
Club Quarters, Times Square - Midtown

Club Quarters, Times Square - Midtown

4 out of 5
Save 100% on your flight
per person
Apr 26 - May 3
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Newark Liberty International Airport Marriott

Newark Liberty International Airport Marriott

4 out of 5
Save 100% on your flight
per person
Apr 13 - Apr 19
found 17 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) 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 5 - May 11
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
Apr 26 - May 3
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Hilton Garden Inn New York/Manhattan-Chelsea

Hilton Garden Inn New York/Manhattan-Chelsea

3 out of 5
Save 100% on your flight
per person
May 5 - May 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
Save 100% on your flight
per person
Apr 13 - Apr 19
found 17 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to New York (NYC)
Red Roof Inn PLUS+ Long Island - Garden City

Red Roof Inn PLUS+ Long Island - Garden City

2.5 out of 5
Save 100% on your flight
per person
Apr 13 - Apr 19
found 17 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to New York (JFK)
Hyatt Grand Central New York

Hyatt Grand Central New York

4 out of 5
Save 100% on your flight
per person
May 5 - May 11
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 5 - May 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 5 - May 11
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.

Wed, Apr 2 - Sat, Apr 5
MCO
Orlando
LGA
New York
$54 Roundtrip, found 2 days ago
$54
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Apr 2 from Orlando to New York, returning Sat, Apr 5, priced at $54 found 2 days ago
Tue, Apr 1 - Wed, Apr 2
FLL
Fort Lauderdale
EWR
New York
$58 Roundtrip, found 19 hours ago
$58
Roundtrip
found 19 hours ago
Select Spirit Airlines flight, departing Tue, Apr 1 from Fort Lauderdale to New York, returning Wed, Apr 2, priced at $58 found 19 hours ago
Sat, Apr 5 - Tue, Apr 8
MIA
Miami
EWR
New York
$59 Roundtrip, found 4 days ago
$59
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Sat, Apr 5 from Miami to New York, returning Tue, Apr 8, priced at $59 found 4 days 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 $169 per night
$169
includes taxes & fees
$148 per night
Mar 17 - Mar 18
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.
Pool
Hot Tub
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
The price is $525 per night
$525
includes taxes & fees
$460 per night
Mar 17 - Mar 18
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
The price is $213 per night
$213
includes taxes & fees
$185 per night
Mar 16 - Mar 17
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
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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.