Shelter Island Holiday Packages

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Top Shelter Island holiday packages

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

Ink 48 Hotel

4.5 out of 5
Manhattan
per person
1 Jun - 8 Jun
found 1 day ago
Return direct flight included
Sydney (SYD) to New York (JFK)
8.4/10 Very Good! (1,179 reviews)
The Dominick

The Dominick

5 out of 5
Manhattan
per person
1 Jun - 8 Jun
found 1 day ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9.2/10 Wonderful! (1,001 reviews)
The Knickerbocker Hotel

The Knickerbocker Hotel

5 out of 5
Manhattan
per person
1 Jun - 8 Jun
found 1 day ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9/10 Wonderful! (1,432 reviews)
Made Hotel

Made Hotel

3.5 out of 5
Manhattan
per person
1 Jun - 8 Jun
found 1 day ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9.4/10 Exceptional! (486 reviews)

Top Shelter Island hotels

Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road, Westbrook, CT
Fully refundableReserve now, pay when you stay
The price is AU$331 per night from 6 May to 7 May
AU$331
includes taxes & fees
6 May - 7 May
Water's Edge Resort & Spa: Business-friendly resort with free WiFi and free valet parking. Located on the waterfront.
"we had a room with a balcony that looked out to the ocean. terrific view. lovely property & staff was very friendly"

Reviewed on 22 Apr. 2025

Water's Edge Resort & Spa
Montauk Yacht Club

Montauk Yacht Club

4 out of 5
32 Star Island Rd, Montauk, NY
The price is AU$427 per night from 28 Apr to 29 Apr
AU$427
includes taxes & fees
28 Apr - 29 Apr
Montauk Yacht Club: Pet-friendly hotel with free WiFi and free parking. Located by the ocean.
"Beautiful place. Wonderful staff"

Reviewed on 25 Apr. 2025

Montauk Yacht Club
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is AU$142 per night from 28 Apr to 29 Apr
AU$142
includes taxes & fees
28 Apr - 29 Apr
Pier Blue Inn Old Saybrook - Essex: Pet-friendly hotel with free WiFi and free parking. Located in the historical district.
"Great night’s sleep."

Reviewed on 18 Apr. 2025

Pier Blue Inn Old Saybrook - Essex
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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.