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 32 32

Hotel 32 32

4 out of 5
Save 100% on your flight
Price was $783, price is now $534 per person
$534
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $3,244, price is now $1,692 per person
$1,692
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Hotel St. James

Hotel St. James

3 out of 5
Save 100% on your flight
Price was $950, price is now $548 per person
$548
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Park Lane New York

Park Lane New York

5 out of 5
Save 100% on your flight
Price was $1,556, price is now $974 per person
$974
per person
Oct 5 - Oct 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Save 100% on your flight
Price was $954, price is now $616 per person
$616
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
CIVILIAN Hotel

CIVILIAN Hotel

4 out of 5
Save 100% on your flight
Price was $902, price is now $601 per person
$601
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Nesva Hotel

Nesva Hotel

2.5 out of 5
Save 100% on your flight
Price was $1,005, price is now $670 per person
$670
per person
Oct 15 - Oct 18
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
33 Hotel, New York City, Seaport

33 Hotel, New York City, Seaport

5 out of 5
Save 100% on your flight
Price was $1,453, price is now $973 per person
$973
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
2 bedroom luxury Empire State VIEW

2 bedroom luxury Empire State VIEW

2 out of 5
Save 100% on your flight
Price was $2,281, price is now $1,542 per person
$1,542
per person
Oct 22 - Oct 25
found 1 hour ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (JFK)
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Save 100% on your flight
Price was $2,666, price is now $1,809 per person
$1,809
per person
Oct 12 - Oct 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
OYO Times Square

OYO Times Square

4 out of 5
Save 100% on your flight
Price was $944, price is now $646 per person
$646
per person
Oct 12 - Oct 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Save 100% on your flight
Price was $1,615, price is now $1,108 per person
$1,108
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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
Save 100% on your flight
Price was $1,061, price is now $625 per person
$625
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $3,317, price is now $1,803 per person
$1,803
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Hotel St. James

Hotel St. James

3 out of 5
Save 100% on your flight
Price was $1,155, price is now $650 per person
$650
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Park Lane New York

Park Lane New York

5 out of 5
Save 100% on your flight
Price was $1,960, price is now $1,169 per person
$1,169
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Save 100% on your flight
Price was $1,531, price is now $915 per person
$915
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,812, price is now $1,089 per person
$1,089
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,752, price is now $1,069 per person
$1,069
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
OYO Times Square

OYO Times Square

4 out of 5
Save 100% on your flight
Price was $1,186, price is now $731 per person
$731
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
San Carlos Hotel

San Carlos Hotel

4.5 out of 5
Save 100% on your flight
Price was $1,771, price is now $1,109 per person
$1,109
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
The William Hotel Midtown, New York

The William Hotel Midtown, New York

3.5 out of 5
Save 100% on your flight
Price was $1,204, price is now $773 per person
$773
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Omni Berkshire Place

Omni Berkshire Place

4 out of 5
Price was $1,806, price is now $1,173 per person
$1,173
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Royalton New York

Royalton New York

4 out of 5
Save 100% on your flight
Price was $1,415, price is now $925 per person
$925
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)

5-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 $1,368, price is now $903 per person
$903
per person
Oct 1 - Oct 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Seven Beach Lane

Seven Beach Lane

2 out of 5
Save 100% on your flight
Price was $2,284, price is now $1,231 per person
$1,231
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New York (JFK)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $4,498, price is now $2,441 per person
$2,441
per person
Oct 6 - Oct 11
found 11 hours ago
Roundtrip non-stop 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
Price was $2,097, price is now $1,282 per person
$1,282
per person
Oct 21 - Oct 26
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) 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 $2,387, price is now $1,516 per person
$1,516
per person
Oct 1 - Oct 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Eurostars Wall Street

Eurostars Wall Street

4 out of 5
Save 100% on your flight
Price was $1,597, price is now $1,030 per person
$1,030
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New York (JFK)
Ink 48 Hotel

Ink 48 Hotel

4.5 out of 5
Save 100% on your flight
Price was $1,540, price is now $995 per person
$995
per person
Oct 11 - Oct 16
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Library Hotel by Library Hotel Collection

Library Hotel by Library Hotel Collection

4 out of 5
Save 100% on your flight
Price was $1,977, price is now $1,298 per person
$1,298
per person
Oct 26 - Oct 31
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New York (JFK)
The Ridge Hotel

The Ridge Hotel

3 out of 5
Save 100% on your flight
Price was $1,629, price is now $1,078 per person
$1,078
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Royalton New York

Royalton New York

4 out of 5
Save 100% on your flight
Price was $1,893, price is now $1,256 per person
$1,256
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Freehand New York

Freehand New York

4 out of 5
Save 100% on your flight
Price was $1,664, price is now $1,110 per person
$1,110
per person
Oct 11 - Oct 16
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
San Carlos Hotel

San Carlos Hotel

4.5 out of 5
Save 100% on your flight
Price was $2,386, price is now $1,592 per person
$1,592
per person
Oct 22 - Oct 27
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)

6-7 night Shelter Island vacations

Price found within the past 48 hours. Click for updated prices.
414 hotel

414 hotel

2 out of 5
Save 100% on your flight
Price was $1,341, price is now $831 per person
$831
per person
Oct 14 - Oct 21
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $4,619, price is now $2,508 per person
$2,508
per person
Oct 23 - Oct 29
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (JFK)
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Save 100% on your flight
Price was $3,024, price is now $1,724 per person
$1,724
per person
Oct 21 - Oct 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $2,445, price is now $1,396 per person
$1,396
per person
Oct 23 - Oct 29
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) 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 $6,301, price is now $3,779 per person
$3,779
per person
Oct 21 - Oct 28
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Hotel Hayden

Hotel Hayden

4 out of 5
Save 100% on your flight
Price was $1,783, price is now $1,105 per person
$1,105
per person
Oct 14 - Oct 21
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Hotel 32 32

Hotel 32 32

4 out of 5
Save 100% on your flight
Price was $1,979, price is now $1,261 per person
$1,261
per person
Oct 14 - Oct 21
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
YOTEL New York Times Square

YOTEL New York Times Square

4 out of 5
Save 100% on your flight
Price was $1,560, price is now $1,004 per person
$1,004
per person
Oct 14 - Oct 21
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) 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 $2,130, price is now $1,414 per person
$1,414
per person
Oct 15 - Oct 21
found 1 day ago
Roundtrip flight included
Chicago (ORD) to New York (JFK)
Aura Hotel Brooklyn

Aura Hotel Brooklyn

4 out of 5
Save 100% on your flight
Price was $1,473, price is now $993 per person
$993
per person
Oct 23 - Oct 29
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (JFK)
Heritage Hotel

Heritage Hotel

2.5 out of 5
Save 100% on your flight
Price was $1,627, price is now $1,098 per person
$1,098
per person
Oct 14 - Oct 21
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Holiday Inn New York City - Wall Street by IHG

Holiday Inn New York City - Wall Street by IHG

3 out of 5
Save 100% on your flight
Price was $1,603, price is now $1,089 per person
$1,089
per person
Oct 14 - Oct 21
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) 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.

Thu, Dec 10 - Sun, Dec 13
FLL
Fort Lauderdale
SWF
Newburgh
$90 Roundtrip, found 2 days ago
$90
Roundtrip
found 2 days ago
Select Allegiant Air flight, departing Thu, Dec 10 from Fort Lauderdale to Newburgh, returning Sun, Dec 13, priced at $90 found 2 days ago
Wed, Sep 23 - Tue, Sep 29
MCO
Orlando
HVN
New Haven
$133 Roundtrip, found 11 hours ago
$133
Roundtrip
found 11 hours ago
Select Avelo Airlines flight, departing Wed, Sep 23 from Orlando to New Haven, returning Tue, Sep 29, priced at $133 found 11 hours ago
Wed, Oct 21 - Tue, Oct 27
MCO
Orlando
EWR
New York
$140 Roundtrip, found 23 hours ago
$140
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Wed, Oct 21 from Orlando to New York, returning Tue, Oct 27, priced at $140 found 23 hours ago

Top rated hotels for your Shelter Island vacation

Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
3.59 mi from city center
$147 nightly
The price is $168 total per night
$168 total
Sep 30 - Oct 1
Total with taxes and fees
When you stay at Sound View Greenport in Greenport, you'll be by the ocean, within a 5-minute drive of Kontokosta Winery and 67 Steps Beach.
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
$93 nightly
The price is $107 total per night
$107 total
Sep 28 - Sep 29
Total with taxes and fees
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.
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39 Southampton NY
13.34 mi from city center
$165 nightly
The price is $188 total per night
$188 total
Oct 1 - Oct 2
Total with taxes and fees
With a stay at The Atlantic Hotel in Southampton, you'll be in the business district, within a 5-minute drive of The Hamptons Beaches and Shinnecock Hills Golf Course.
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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.