Cheap Vacations in Shelter Island

Choose two or more items and save on your trip:

3-night Shelter Island vacations

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

Allegria Hotel

4 out of 5
Price was $1,172, price is now $842 per person
$842
per person
Jul 10 - Jul 13
found 8 hours ago
Roundtrip 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
Price was $2,463, price is now $1,397 per person
$1,397
per person
Jul 23 - Jul 26
found 23 hours ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Price was $2,031, price is now $1,245 per person
$1,245
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
New York Marriott Marquis

New York Marriott Marquis

4.5 out of 5
Save 100% on your flight
Price was $1,650, price is now $1,048 per person
$1,048
per person
Jul 3 - Jul 6
found 2 days ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
The Surrey A Corinthia Hotel

The Surrey A Corinthia Hotel

5 out of 5
Price was $2,721, price is now $1,909 per person
$1,909
per person
Jul 23 - Jul 26
found 23 hours 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
Price was $1,413, price is now $1,000 per person
$1,000
per person
Jul 3 - Jul 6
found 2 days ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Price was $2,174, price is now $1,549 per person
$1,549
per person
Jul 23 - Jul 26
found 23 hours ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Price was $1,321, price is now $948 per person
$948
per person
Jul 3 - Jul 6
found 2 days ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Park Lane New York

Park Lane New York

5 out of 5
Price was $1,197, price is now $870 per person
$870
per person
Jul 22 - Jul 25
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Faena New York

Faena New York

5 out of 5
Price was $2,015, price is now $1,480 per person
$1,480
per person
Jul 23 - Jul 26
found 23 hours ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
The Wall Street Inn

The Wall Street Inn

3 out of 5
Save 100% on your flight
Price was $1,376, price is now $1,014 per person
$1,014
per person
Jul 17 - Jul 20
found 4 hours ago
Roundtrip flight included
San Juan (SJU) to Newark Liberty Intl. Airport (EWR)
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Price was $1,341, price is now $994 per person
$994
per person
Jul 16 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)

4-night Shelter Island vacations

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

Peachtree Suites

2.5 out of 5
Price was $884, price is now $617 per person
$617
per person
Jul 20 - Jul 24
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
Dream Hotel Bronx

Dream Hotel Bronx

2 out of 5
Save 100% on your flight
Price was $1,497, price is now $888 per person
$888
per person
Jul 16 - Jul 20
found 24 hours ago
Roundtrip flight included
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $3,275, price is now $2,108 per person
$2,108
per person
Jul 6 - Jul 10
found 11 hours ago
Roundtrip non-stop flight included
Chicago (ORD) 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 $1,655, price is now $1,100 per person
$1,100
per person
Jul 14 - Jul 18
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $1,213, price is now $813 per person
$813
per person
Jul 6 - Jul 10
found 11 hours ago
Roundtrip non-stop flight included
Chicago (ORD) 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 $5,437, price is now $3,652 per person
$3,652
per person
Jul 16 - Jul 20
found 21 hours 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 $1,651, price is now $1,126 per person
$1,126
per person
Jul 6 - Jul 10
found 11 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to New York (JFK)
Radio Hotel

Radio Hotel

4 out of 5
Price was $1,189, price is now $822 per person
$822
per person
Jul 6 - Jul 10
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
Oheka Castle Hotel & Estate

Oheka Castle Hotel & Estate

3.5 out of 5
Price was $1,271, price is now $902 per person
$902
per person
Jul 6 - Jul 10
found 11 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to New York (JFK)
Allegria Hotel

Allegria Hotel

4 out of 5
Save 100% on your flight
Price was $1,516, price is now $1,097 per person
$1,097
per person
Jul 16 - Jul 20
found 9 hours ago
Roundtrip flight included
San Juan (SJU) to New York (JFK)
Hampton Inn Garden City Long Island

Hampton Inn Garden City Long Island

2.5 out of 5
Price was $1,159, price is now $842 per person
$842
per person
Jul 17 - Jul 21
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New York (JFK)
Pendry Natirar

Pendry Natirar

5 out of 5
Price was $2,579, price is now $1,883 per person
$1,883
per person
Jul 6 - Jul 10
found 11 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)

5-night Shelter Island vacations

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Hotel Newark Airport

DoubleTree by Hilton Hotel Newark Airport

4 out of 5
Price was $872, price is now $641 per person
$641
per person
Jul 22 - Jul 27
just found
Roundtrip flight included
San Juan (SJU) 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 $2,616, price is now $1,556 per person
$1,556
per person
Jul 15 - Jul 20
found 1 day ago
Roundtrip 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 $5,872, price is now $3,599 per person
$3,599
per person
Jul 15 - Jul 20
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Row NYC

Row NYC

4 out of 5
Save 100% on your flight
Price was $2,037, price is now $1,343 per person
$1,343
per person
Jul 15 - Jul 20
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
The George

The George

4 out of 5
Save 100% on your flight
Price was $2,663, price is now $1,810 per person
$1,810
per person
Jul 15 - Jul 20
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
OYO Times Square

OYO Times Square

4 out of 5
Save 100% on your flight
Price was $1,770, price is now $1,255 per person
$1,255
per person
Jul 15 - Jul 20
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
Hampton Inn Garden City Long Island

Hampton Inn Garden City Long Island

2.5 out of 5
Save 100% on your flight
Price was $1,404, price is now $1,008 per person
$1,008
per person
Jul 14 - Jul 19
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Hotel Edison Times Square

Hotel Edison Times Square

4 out of 5
Save 100% on your flight
Price was $1,874, price is now $1,348 per person
$1,348
per person
Jul 15 - Jul 20
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
Hotel Belleclaire

Hotel Belleclaire

4 out of 5
Save 100% on your flight
Price was $1,821, price is now $1,324 per person
$1,324
per person
Jul 15 - Jul 20
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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 $2,221, price is now $1,631 per person
$1,631
per person
Jul 15 - Jul 20
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
The Pierre, A Taj Hotel, New York

The Pierre, A Taj Hotel, New York

5 out of 5
Save 100% on your flight
Price was $9,883, price is now $7,317 per person
$7,317
per person
Jul 15 - Jul 20
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Hotel Boutique at Grand Central

Hotel Boutique at Grand Central

4 out of 5
Save 100% on your flight
Price was $1,763, price is now $1,309 per person
$1,309
per person
Jul 14 - Jul 19
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.
OYO Times Square

OYO Times Square

4 out of 5
Price was $1,177, price is now $870 per person
$870
per person
Jul 8 - Jul 14
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
Park Lane New York

Park Lane New York

5 out of 5
Save 100% on your flight
Price was $4,029, price is now $2,431 per person
$2,431
per person
Jul 12 - Jul 19
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New York (JFK)
Radio Hotel

Radio Hotel

4 out of 5
Save 100% on your flight
Price was $1,935, price is now $1,206 per person
$1,206
per person
Jul 4 - Jul 11
found 1 hour ago
Roundtrip flight included
Los Angeles (LAX) 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 $6,671, price is now $4,477 per person
$4,477
per person
Jul 14 - Jul 20
just found
Roundtrip flight included
San Juan (SJU) to New York (JFK)
The George

The George

4 out of 5
Save 100% on your flight
Price was $1,907, price is now $1,314 per person
$1,314
per person
Jul 8 - Jul 14
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Newark Liberty Intl. Airport (EWR)
Park South Hotel, part of JdV by Hyatt

Park South Hotel, part of JdV by Hyatt

4 out of 5
Save 100% on your flight
Price was $1,615, price is now $1,135 per person
$1,135
per person
Jul 8 - Jul 14
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (JFK)
WestHouse New York

WestHouse New York

5 out of 5
Save 100% on your flight
Price was $2,755, price is now $1,967 per person
$1,967
per person
Jul 12 - Jul 19
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New York (JFK)
42 Hotel

42 Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,936, price is now $1,385 per person
$1,385
per person
Jul 18 - Jul 24
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Newark Liberty Intl. Airport (EWR)
The Westin New York Grand Central

The Westin New York Grand Central

4.5 out of 5
Save 100% on your flight
Price was $1,647, price is now $1,201 per person
$1,201
per person
Jul 8 - Jul 14
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
Hotel Belleclaire

Hotel Belleclaire

4 out of 5
Save 100% on your flight
Price was $1,577, price is now $1,158 per person
$1,158
per person
Jul 8 - Jul 14
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (JFK)
Off Soho Suites Hotel

Off Soho Suites Hotel

2 out of 5
Save 100% on your flight
Price was $1,738, price is now $1,309 per person
$1,309
per person
Jul 8 - Jul 14
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (JFK)
Hilton New York Fashion District

Hilton New York Fashion District

4 out of 5
Save 100% on your flight
Price was $1,526, price is now $1,155 per person
$1,155
per person
Jul 8 - Jul 14
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) 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.

Sat, Jul 4 - Wed, Jul 8
ATL
Atlanta
LGA
New York
$101 Roundtrip, found 13 hours ago
$101
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Sat, Jul 4 from Atlanta to New York, returning Wed, Jul 8, priced at $101 found 13 hours ago
Tue, Jul 21 - Wed, Aug 12
ATL
Atlanta
JFK
New York
$111 Roundtrip, found 8 hours ago
$111
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Tue, Jul 21 from Atlanta to New York, returning Wed, Aug 12, priced at $111 found 8 hours ago
Fri, Jul 24 - Tue, Jul 28
ATL
Atlanta
EWR
New York
$118 Roundtrip, found 13 hours ago
$118
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Fri, Jul 24 from Atlanta to New York, returning Tue, Jul 28, priced at $118 found 13 hours ago
Sat, Jun 27 - Sat, Jul 11
MCO
Orlando
LGA
New York
$138 Roundtrip, found 3 hours ago
$138
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, Jun 27 from Orlando to New York, returning Sat, Jul 11, priced at $138 found 3 hours ago
Thu, Jul 16 - Wed, Jul 22
MCO
Orlando
HVN
New Haven
$143 Roundtrip, found 2 days ago
$143
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Jul 16 from Orlando to New Haven, returning Wed, Jul 22, priced at $143 found 2 days ago
Wed, Sep 9 - Sat, Sep 12
TPA
Tampa
LGA
New York
$157 Roundtrip, found 4 days ago
$157
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Sep 9 from Tampa to New York, returning Sat, Sep 12, priced at $157 found 4 days 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
$852 nightly
The price is $973 total per night
$973 total
Jun 7 - Jun 8
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
$286 nightly
The price is $327 total per night
$327 total
Jun 4 - Jun 5
Total with taxes and fees
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
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39 Southampton NY
13.34 mi from city center
$221 nightly
The price is $252 total per night
$252 total
Jun 4 - Jun 5
Total with taxes and fees
When you stay at The Atlantic Hotel in Southampton, you'll be in the business district, within a 5-minute drive of Shinnecock Hills Golf Course and The Hamptons Beaches.
Pool
Pet friendly
Don't see what you're looking for?
See all available properties in Shelter Island
View all properties
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.