Shelter Island Holiday Packages

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Top Shelter Island holiday packages

Price found within the past 48 hours. Click for updated prices.
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
Price was AU$7,599, price is now AU$5,073 per person
AU$5,073
per person
7 Dec - 12 Dec
found 1 day ago
Return direct flight included
Melbourne (MEL) to New York (JFK)
8.8/10 Excellent! (1,200 reviews)

Sela V Hotel

Sela V Hotel

4 out of 5
Price was AU$9,439, price is now AU$6,177 per person
AU$6,177
per person
7 Dec - 12 Dec
found 1 day ago
Return direct flight included
Melbourne (MEL) to New York (JFK)
9.4/10 Exceptional! (284 reviews)
Nice hotel and room - but no particularly comfortable/cozy - very industrial and minimal. There really are no in room amenities ( no minibar etc) or room service/food on premises - so plan accordingly

Reviewed on 22 Oct 2026

Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything

3.5 out of 5
Price was AU$8,051, price is now AU$5,355 per person
AU$5,355
per person
7 Dec - 12 Dec
found 1 day ago
Return direct flight included
Melbourne (MEL) to New York (JFK)
No reviews

Parkway House Goshen Family-Friendly Bed & Breakfast

Parkway House Goshen Family-Friendly Bed & Breakfast

3 out of 5
Price was AU$8,529, price is now AU$5,693 per person
AU$5,693
per person
7 Dec - 12 Dec
found 1 day ago
Return direct flight included
Melbourne (MEL) to New York (JFK)
10/10 Exceptional! (34 reviews)
This property is exquisite and so beautifully decorated. Our hostess, Emily, treated us to a fresh and wonderful breakfast. Checking in and out was easy. Rooms are impeccably clean and equipped with everything you’ll need to visit your cadets or enjoy the Hudson River Valley.

Reviewed on 16 Oct 2026

Motel House

Motel House

2 out of 5
Fairmount
Price was AU$7,621, price is now AU$5,092 per person
AU$5,092
per person
7 Dec - 12 Dec
found 1 day ago
Return direct flight included
Melbourne (MEL) to New York (JFK)
4.8/10 (33 reviews)
We couldn’t even get to the room because the keys to the house didn’t work. After over an hour of back and forth on a cobweb infested porch, we thankfully got refunded and went elsewhere.

Reviewed on 12 Sept 2026

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$333 per night from 1 Nov to 2 Nov
AU$333
1 Nov - 2 Nov
includes taxes & fees
Water's Edge Resort & Spa: Business-friendly resort with free WiFi and free valet parking. Located on the waterfront.
"Great"

Reviewed on 21 Oct 2026

Opens in a new windowWater's Edge Resort & Spa
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundable
The price is AU$134 per night from 15 Nov to 16 Nov
AU$134
15 Nov - 16 Nov
includes taxes & fees
Pier Blue Inn Old Saybrook - Essex: Pet-friendly hotel with free WiFi and free parking. Located near a train station.
"Staff was friendly. Grounds very well kept. But rooms are very dated."

Reviewed on 22 Oct 2026

Opens in a new windowPier Blue Inn Old Saybrook - Essex
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
The price is AU$714 per night from 10 Nov to 11 Nov
AU$714
10 Nov - 11 Nov
includes taxes & fees
Gurney's Montauk Resort & Seawater Spa: Pet-friendly resort with an indoor pool and 2 restaurants. Located by the ocean.
Opens in a new windowGurney's Montauk Resort & Seawater Spa
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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.

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