Shelter Island Vacation Packages
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Top Shelter Island vacation package deals
Price found within the past 48 hours. Click for updated prices.
3.0-star property
Parkway House Goshen Family-Friendly Bed & Breakfast
10/10 Exceptional! (40 reviews)
Jan 15 - Jan 18
3 night stay
Atlanta (ATL) to New York (JFK)
Frontier Airlines • Roundtrip • Coach
Price was $737, price is now $455 per person
$455
per person
found 7 hours ago
What a amazing property the stuff are amazin
Reviewed on Nov 1, 2026
3.5-star property
The William Hotel Midtown, New York
Manhattan
9.4/10 Exceptional! (275 reviews)
Dec 18 - Dec 21
3 night stay
Atlanta (ATL) to New York (JFK)
Frontier Airlines • Roundtrip • Coach
Price was $1,978, price is now $1,101 per person
$1,101
per person
found 1 day ago
The bath towel shelf in the shower was so high up, I had to stand on my tippy toes to grab a towel and I’m 5ft 5in. Likewise, the little mirror by the entry door was hung at a height for a 6 foot man to check his hair. The pillows felt like swim floaties. Great location though. And no smartly situated outlets for recharging phone and laptop.
Reviewed on Nov 4, 2026
3.0-star property
The Wall Street Inn
Manhattan
8.8/10 Excellent! (1,002 reviews)
Dec 11 - Dec 18
7 night stay
Atlanta (ATL) to New York (JFK)
Frontier Airlines • Roundtrip • Coach
Price was $2,148, price is now $1,303 per person
$1,303
per person
found 1 day ago
Extremely friendly staff, great service and beautiful hotel!
Reviewed on Nov 1, 2026
Top rated hotels for your Shelter Island vacation package
Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway Montauk NY
18.43 mi from city center
$413 nightly
The price is $472 total per night
$472 total
Nov 29 - Nov 30
Total with taxes and fees
Guests of Gurney's Montauk Resort & Seawater Spa have access to a private beach, a full-service spa, and an indoor pool. The front desk is staffed 24/7 to help with concierge services, securing valuables, and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach resort include a 24-hour gym, meeting rooms, and a conference center.
On private beach
Pool
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Free Cancellation
Reserve now, pay when you stay
15.59 mi from city center
$205 nightly
The price is $236 total per night
$236 total
Nov 10 - Nov 11
Total with taxes and fees
Guests of Water's Edge Resort & Spa have access to a private beach, a full-service spa, and an indoor pool. You can put free valet parking to good use if you drive. The 24-hour front desk has staff standing by to help with concierge services, dry cleaning/laundry, and luggage storage. Other amenities at this beach resort include a gym, a sauna, and outdoor tennis courts.
On private beach
Pool
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Free Cancellation
Reserve now, pay when you stay
15.48 mi from city center
$77 nightly
The price is $88 total per night
$88 total
Nov 5 - Nov 6
Total with taxes and fees
Pier Blue Inn Old Saybrook - Essex features free WiFi in public areas and a picnic area. Free parking is included with your stay. Staff members can answer questions about accommodations, and also provide front-desk service during limited hours. If you like to take your furry friend along on your adventures, this pet-friendly property offers an off-leash area.
Pet friendly
Parking included
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.
Things to do
Half-Day Private Long Island Wine Tour Experience
$279
per adult
Half Day(PM) North Fork Private Wine & Food Tour by Local Expert
$439
per adult
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