Deals on vacations and trips to Shelter Island
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Shelter Island flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
The Inn At Fox Hollow Hotel
Save 100% on your flight
per person
Nov 4 - Nov 7
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This hotel features 2 bars/lounges, a poolside bar, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free train station pick-up. Enjoy the 24-hour gym and perks like free self parking and a free area shuttle.
Sound View Greenport
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
A private beach and a restaurant are featured at this smoke-free hotel. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like continental breakfast and WiFi in public areas.
The Harbor Front Inn
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This hotel features a 24-hour gym and a seasonal outdoor pool. Business travelers can take advantage of the free WiFi in public areas. Enjoy the free continental breakfast each morning.
INNSiDE by Meliá New York Nomad
Manhattan
per person
Oct 19 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A terrace, limo/town car service, and a picnic area are also on offer.
Harpoon House
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This bed & breakfast features a restaurant and 3 bars/lounges. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop, a terrace, and a garden are also on offer.
Top Shelter Island hotels deals
Marram
21 Oceanview Terrace, Montauk, NY
$529 nightly
The price is $604 total per night
$604 total
Sep 2 - Sep 3
Total includes taxes and fees
A seasonal outdoor pool, free self parking, and wedding services are featured at this hotel. WiFi in public areas is free. A terrace, a garden, and luggage storage are also on offer.
Pool
Parking included
Beachcomber Resort at Montauk
727 Old Montauk Highway, Montauk, NY
$320 nightly
The price is $361 total per night
$361 total
Sep 2 - Sep 3
Total includes taxes and fees
This hotel features a gym and an outdoor tennis court. Enjoy the seasonal outdoor pool and perks like free WiFi. A sauna is also provided.
Pool
Free WiFi
Sound View Greenport
58775 County Rd 48, Greenport, NY
$332 nightly
The price is $380 total per night
$380 total
Sep 9 - Sep 10
Total includes taxes and fees
A private beach and a restaurant are featured at this smoke-free hotel. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like continental breakfast and WiFi in public areas.
On private beach
Pool
Montauk Yacht Club
32 Star Island Rd, Montauk, NY
$432 nightly
The price is $494 total per night
$494 total
Sep 1 - Sep 2
Total includes taxes and fees
This hotel features a private beach, a marina, and 2 restaurants. Traveling on business? Take advantage of the 5 conference rooms, along with free WiFi in public areas. Enjoy the 2 outdoor pools and get free self parking.
On private beach
Pool
Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway, Montauk, NY
$716 nightly
The price is $818 total per night
$818 total
Sep 14 - Sep 15
Total includes taxes and fees
This resort features a private beach, a full-service spa, and 2 restaurants. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside bar. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls.
On private beach
Pool
Saybrook Point Resort & Marina
2 Bridge St, Old Saybrook, CT
Free Cancellation
Reserve now, pay when you stay
$419 nightly
The price is $479 total per night
$479 total
Aug 26 - Aug 27
Total includes taxes and fees
A full-service spa, a marina, and 2 outdoor pools are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and free train station pick-up. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and a shopping center shuttle.
Pool
Hot Tub
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.
Popular places to visit
Gardiner's Bay Country Club
Enjoy a round of golf in Shelter Island at Gardiner's Bay Country Club. Stroll along the area's waterfront or simply enjoy its wineries.
Shelter Island Whale's Tail
You can take time to visit Shelter Island Whale's Tail during your travels to Shelter Island. Wander the beaches and waterfront in the area.
Mashomack Preserve
Explore the great outdoors at Mashomack Preserve, a lovely green space in Shelter Island. Stroll along the beaches or discover the sunsets in this family-friendly area.
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