
Shelter Island Vacation Packages
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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 10 hours ago
What a amazing property the stuff are amazin
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
The price is $472 total per night
$472 total
per night
Nov 29 - Nov 30
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
The price is $236 total per night
$236 total
per night
Nov 10 - Nov 11
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
The price is $88 total per night
$88 total
per night
Nov 5 - Nov 6
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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