Cheap Vacations in Shelter Island
- Shelter Island vacations
- 3-night Shelter Island vacations
- 4-night Shelter Island vacations
- 5-night Shelter Island vacations
- 6-7 night Shelter Island vacations
3-night Shelter Island vacations
Price found within the past 48 hours. Click for updated prices.
4-night Shelter Island vacations
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5-night Shelter Island vacations
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6-7 night Shelter Island vacations
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Flight deals to Shelter Island
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
MCO
Orlando
EWR
New York
$79 Roundtrip, found 1 hour ago
$79
Roundtrip
found 1 hour ago
FLL
Fort Lauderdale
EWR
New York
$86 Roundtrip, found 2 days ago
$86
Roundtrip
found 2 days ago
MCO
Orlando
LGA
New York
$87 Roundtrip, found 4 hours ago
$87
Roundtrip
found 4 hours ago
Top rated hotels for your Shelter Island vacation
Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway Montauk NY
18.43 mi from city center
$594 nightly
The price is $679 total per night
$679 total
Apr 19 - Apr 20
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
236 Edgemere St. Montauk NY
20.31 mi from city center
$168 nightly
The price is $192 total per night
$192 total
Apr 20 - Apr 21
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
Sound View Greenport
58775 County Rd 48 Greenport NY
3.59 mi from city center
$244 nightly
The price is $279 total per night
$279 total
May 3 - May 4
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.
On private beach
Pool
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
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- Southold Hotels
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- Beach Resorts & in Sag Harbor
- Hotels near Lenz Winery
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- 5 Star Hotels in Greenport
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- Winery Hotels in Sag Harbor
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- Hostels in Mattituck
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- Chalets in Sagaponack
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- Hotels with Bars in Sag Harbor
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- Oceanfront Hotels in Greenport
- Arcade Hotels in Amagansett
- Cabin Rentals in Sag Harbor
- Cabin Rentals in Shelter Island
- Hotels with WiFi in Amagansett
- 3 Star Hotels in Southold
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- Hotels with Pools in Bridgehampton
- Hotels with Air Conditioning in Sag Harbor
- Kid Friendly Hotels in Amagansett
- Extended Stay Hotels in Amagansett
- Hotels near Orient Beach State Park
^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.
