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.
East Norwich Inn

East Norwich Inn

2.5 out of 5
Price was $605, price is now $439 per person
$439
per person
Aug 21 - Aug 24
found 16 hours ago
Roundtrip non-stop flight included
Houston (HOU) to New York (JFK)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $2,559, price is now $1,669 per person
$1,669
per person
Aug 21 - Aug 24
found 18 hours ago
Roundtrip flight included
Houston (IAH) 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
Price was $2,096, price is now $1,380 per person
$1,380
per person
Aug 25 - Aug 28
found 5 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to New York (JFK)
Pendry Natirar

Pendry Natirar

5 out of 5
Save 100% on your flight
Price was $1,835, price is now $1,248 per person
$1,248
per person
Aug 25 - Aug 28
found 5 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to New York (JFK)
Radio Hotel

Radio Hotel

4 out of 5
Price was $672, price is now $460 per person
$460
per person
Aug 21 - Aug 24
found 16 hours ago
Roundtrip non-stop flight included
Houston (HOU) to New York (JFK)
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Save 100% on your flight
Price was $1,379, price is now $953 per person
$953
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip flight included
Houston (HOU) to New York (JFK)
The Fifty Sonesta Hotel New York

The Fifty Sonesta Hotel New York

4 out of 5
Save 100% on your flight
Price was $889, price is now $627 per person
$627
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) 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 $1,539, price is now $1,108 per person
$1,108
per person
Sep 3 - Sep 6
found 14 hours ago
Roundtrip non-stop flight included
Burbank (BUR) to New York (JFK)
Hotel St. James

Hotel St. James

3 out of 5
Price was $1,237, price is now $897 per person
$897
per person
Sep 3 - Sep 6
found 14 hours ago
Roundtrip non-stop flight included
Burbank (BUR) to New York (JFK)
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Price was $658, price is now $487 per person
$487
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to New York (JFK)
Casablanca Hotel by Library Hotel Collection

Casablanca Hotel by Library Hotel Collection

4 out of 5
Save 100% on your flight
Price was $1,128, price is now $843 per person
$843
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New York (JFK)
Eurostars Wall Street

Eurostars Wall Street

4 out of 5
Price was $720, price is now $545 per person
$545
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to New York (JFK)

4-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
Price was $795, price is now $567 per person
$567
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to New York (JFK)
San Carlos Hotel

San Carlos Hotel

4.5 out of 5
Save 100% on your flight
Price was $1,500, price is now $973 per person
$973
per person
Sep 7 - Sep 11
found 1 day ago
Roundtrip flight included
Houston (HOU) to New York (JFK)
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Save 100% on your flight
Price was $1,664, price is now $1,086 per person
$1,086
per person
Sep 5 - Sep 9
found 1 day ago
Roundtrip flight included
Houston (HOU) to New York (JFK)
Hotel 32 32

Hotel 32 32

4 out of 5
Save 100% on your flight
Price was $1,231, price is now $812 per person
$812
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) 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 $1,528, price is now $1,021 per person
$1,021
per person
Aug 20 - Aug 24
found 19 hours ago
Roundtrip non-stop flight included
Ontario Intl. Airport (ONT) to New York (JFK)
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Save 100% on your flight
Price was $1,962, price is now $1,331 per person
$1,331
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to New York (JFK)
Park Lane New York

Park Lane New York

5 out of 5
Save 100% on your flight
Price was $1,338, price is now $916 per person
$916
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) 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 $2,051, price is now $1,421 per person
$1,421
per person
Sep 3 - Sep 7
found 2 hours ago
Roundtrip flight included
Burbank (BUR) to New York (JFK)
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Save 100% on your flight
Price was $1,195, price is now $834 per person
$834
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) 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 $1,906, price is now $1,337 per person
$1,337
per person
Sep 3 - Sep 7
found 2 hours ago
Roundtrip flight included
Burbank (BUR) to New York (JFK)
The Shelburne Sonesta New York

The Shelburne Sonesta New York

4 out of 5
Save 100% on your flight
Price was $1,280, price is now $910 per person
$910
per person
Sep 5 - Sep 9
found 1 day ago
Roundtrip flight included
Houston (HOU) to New York (JFK)
The Sohotel

The Sohotel

4 out of 5
Save 100% on your flight
Price was $1,186, price is now $846 per person
$846
per person
Sep 5 - Sep 9
found 1 day ago
Roundtrip flight included
Houston (HOU) to New York (JFK)

5-night Shelter Island vacations

Price found within the past 48 hours. Click for updated prices.
Morris Guest House

Morris Guest House

3 out of 5
Save 100% on your flight
Price was $1,105, price is now $780 per person
$780
per person
Sep 9 - Sep 14
found 23 hours ago
Roundtrip non-stop flight included
Los Angeles (QLA) to New York (JFK)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $5,435, price is now $3,329 per person
$3,329
per person
Sep 3 - Sep 8
found 11 hours ago
Roundtrip non-stop flight included
Los Angeles (QLA) to New York (JFK)
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Save 100% on your flight
Price was $4,117, price is now $2,603 per person
$2,603
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Los Angeles (QLA) to New York (JFK)
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Save 100% on your flight
Price was $2,334, price is now $1,514 per person
$1,514
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Houston (IAH) to New York (JFK)
Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Save 100% on your flight
Price was $2,465, price is now $1,649 per person
$1,649
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Houston (IAH) 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
Price was $1,418, price is now $985 per person
$985
per person
Aug 31 - Sep 5
found 1 day ago
Roundtrip flight included
Houston (IAH) to New York (JFK)
Aura Hotel Times Square

Aura Hotel Times Square

4 out of 5
Price was $1,453, price is now $1,015 per person
$1,015
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Citadines Connect Fifth Avenue New York

Citadines Connect Fifth Avenue New York

3.5 out of 5
Save 100% on your flight
Price was $1,206, price is now $845 per person
$845
per person
Aug 31 - Sep 5
found 1 day ago
Roundtrip flight included
Houston (IAH) to New York (JFK)
The Chemists’ Club Hotel

The Chemists’ Club Hotel

4 out of 5
Save 100% on your flight
Price was $2,229, price is now $1,565 per person
$1,565
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Houston (IAH) to New York (JFK)
Hampton Inn Madison Square Garden Area Hotel

Hampton Inn Madison Square Garden Area Hotel

3 out of 5
Save 100% on your flight
Price was $1,424, price is now $1,002 per person
$1,002
per person
Aug 31 - Sep 5
found 1 day ago
Roundtrip flight included
Houston (IAH) to New York (JFK)
Pendry Manhattan West

Pendry Manhattan West

5 out of 5
Save 100% on your flight
Price was $4,493, price is now $3,162 per person
$3,162
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Houston (IAH) to New York (JFK)
The Mark

The Mark

5 out of 5
Save 100% on your flight
Price was $5,977, price is now $4,237 per person
$4,237
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Houston (IAH) to New York (JFK)

6-7 night Shelter Island vacations

Price found within the past 48 hours. Click for updated prices.
Radio Hotel

Radio Hotel

4 out of 5
Save 100% on your flight
Price was $1,177, price is now $723 per person
$723
per person
Aug 25 - Aug 31
found 6 hours ago
Roundtrip flight included
Houston (IAH) 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 $2,640, price is now $1,451 per person
$1,451
per person
Aug 30 - Sep 6
found 15 hours ago
Roundtrip flight included
Houston (HOU) 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 $2,406, price is now $1,337 per person
$1,337
per person
Aug 30 - Sep 6
found 15 hours ago
Roundtrip flight included
Houston (HOU) to New York (JFK)
Hyatt Herald Square New York

Hyatt Herald Square New York

4 out of 5
Save 100% on your flight
Price was $1,846, price is now $1,155 per person
$1,155
per person
Aug 30 - Sep 6
found 15 hours ago
Roundtrip flight included
Houston (HOU) to New York (JFK)
Hampton Inn Madison Square Garden Area Hotel

Hampton Inn Madison Square Garden Area Hotel

3 out of 5
Save 100% on your flight
Price was $1,865, price is now $1,220 per person
$1,220
per person
Aug 30 - Sep 6
found 15 hours ago
Roundtrip flight included
Houston (HOU) to New York (JFK)
Park Central Hotel New York

Park Central Hotel New York

4 out of 5
Save 100% on your flight
Price was $1,372, price is now $898 per person
$898
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to New York (JFK)
The Hotel @ Fifth Avenue

The Hotel @ Fifth Avenue

3.5 out of 5
Save 100% on your flight
Price was $1,203, price is now $814 per person
$814
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to New York (JFK)
Citadines Connect Fifth Avenue New York

Citadines Connect Fifth Avenue New York

3.5 out of 5
Save 100% on your flight
Price was $1,613, price is now $1,107 per person
$1,107
per person
Sep 6 - Sep 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 $1,780, price is now $1,251 per person
$1,251
per person
Aug 24 - Aug 30
found 1 day ago
Roundtrip flight included
Houston (HOU) to New York (JFK)
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Save 100% on your flight
Price was $1,157, price is now $815 per person
$815
per person
Aug 24 - Aug 30
found 1 day ago
Roundtrip flight included
Houston (HOU) to New York (JFK)
The Gregorian New York City

The Gregorian New York City

3.5 out of 5
Save 100% on your flight
Price was $1,235, price is now $871 per person
$871
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to New York (JFK)
Pod 51

Pod 51

3 out of 5
Save 100% on your flight
Price was $1,073, price is now $768 per person
$768
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) 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.

Sat, Oct 17 - Wed, Oct 21
MCO
Orlando
LGA
New York
$86 Roundtrip, found 3 days ago
$86
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Oct 17 from Orlando to New York, returning Wed, Oct 21, priced at $86 found 3 days ago
Sat, Nov 14 - Tue, Nov 17
MCO
Orlando
EWR
New York
$86 Roundtrip, found 1 day ago
$86
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Nov 14 from Orlando to New York, returning Tue, Nov 17, priced at $86 found 1 day ago
Thu, Aug 6 - Thu, Aug 13
FLL
Fort Lauderdale
SWF
Newburgh
$104 Roundtrip, found 3 days ago
$104
Roundtrip
found 3 days ago
Select Allegiant Air flight, departing Thu, Aug 6 from Fort Lauderdale to Newburgh, returning Thu, Aug 13, priced at $104 found 3 days ago

Top rated hotels for your Shelter Island vacation

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
The price is $105 total per night
$105 total
per night
Jul 19 - Jul 20
With a stay at Pier Blue Inn Old Saybrook - Essex in Old Saybrook (Saybrook Manor), you'll be within a 15-minute drive of Hammonasset Beach State Park and Chalker Beach.
Pet friendly
Parking included
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 $1,405 total per night
$1,405 total
per night
Jul 26 - Jul 27
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
The price is $549 total per night
$549 total
per night
Aug 3 - Aug 4
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 Lighthouse.
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See all available properties in Shelter Island
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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.

Top Picks

^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.