Shelter Island Vacation Packages
Book a Stay + Flight or Car to save on your trip
Top Shelter Island vacation package deals
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hotel Riu Plaza Manhattan Times Square
Manhattan
9.2/10 Wonderful! (4,080 reviews)
Dec 8 - Dec 11
3 night stay
Atlanta (ATL) to New York (JFK)
Frontier Airlines • Roundtrip • Coach
Price was $2,344, price is now $1,392 per person
$1,392
per person
found 1 day ago
The location was excellent. From our hotel room, we could see Times Square. There were no complimentary toothbrushes; my sister-in-law lost her luggage. We had to pay at the bar. The atmosphere was great in the lobby. The elevators took a long time as it was very busy. Overall, the hotel was clean and comfortable, and I would stay again.
Reviewed on Nov 3, 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
$403 nightly
The price is $460 total per night
$460 total
Nov 9 - Nov 10
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, luggage storage, and securing valuables. 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
Explore More Ways to Travel with Travelocity
- Silver Beach Hotels
- Hotels near Greenport Carousel
- Hotels near Sunset Beach
- Hotels near Camera Obscura
- Hotels near Railroad Museum of Long Island
- Hotels near East End Seaport Maritime Museum
- Hotels near Shelter Island Whale's Tail
- Hotels near Gardiner's Bay Country Club
- Hotels near Sylvester Manor
- Hotels near Havens House
- Hotels near Shell Beach
- B&B in Greenport Station
- Vacation Homes in Greenport Station
- 5 Star Hotels in Greenport
- B&B in Greenport
- Beach Resorts & in Greenport
- Boutique Hotels in Greenport
- Business Hotels in Greenport
- Gay Friendly Hotels in Greenport
- Historic Hotels in Greenport
- Hotels with Pool in Greenport
- Hotels with WiFi in Greenport
- Hotels with Bar in Greenport
- Hotels with Free Parking in Greenport
- Hotels with Kitchenettes in Greenport
- Luxury Hotels in Greenport
- Oceanfront Hotels in Greenport
- Pet Friendly Hotels in Greenport
- Romantic Getaways & Hotels in Greenport
- Ski Resorts & in Greenport
- Spa Resorts & in Greenport
- Hotels with a Wedding Venue in Greenport
- Winery Hotels in Greenport
- Greenport Hotels
- Houseboats in Greenport
- Inns in Greenport
- Motels in Greenport
- Vacation Homes in Greenport
- Villas in Greenport
- Hotels near Shelter Island Historical Society
- Hotels near Wades Beach
- Cottages in Shelter Island Heights
- Kid Friendly Hotels in Shelter Island Heights
- Hotels with Pool in Shelter Island Heights
- Hotels with Bar in Shelter Island Heights
- Hotels with a Gym in Shelter Island Heights
- Hotels with Hot Tubs in Shelter Island Heights
- Winery Hotels in Shelter Island Heights
- Shelter Island Heights Hotels
- Houseboats in Shelter Island Heights
- Resorts in Shelter Island Heights
- B&B in Dering Harbor
- Flights to Greenport
- Flights from Boston to Greenport
- Flights from Chicago to Greenport
- Flights from Cleveland to Greenport
- Flights from Columbus to Greenport
- Flights from New Orleans to Greenport
- Flights from Phoenix to Greenport
- Flights from Raleigh to Greenport
- Flights from Toronto to Greenport
- Flights from San Juan to Greenport
- Flights to Shelter Island Heights
- Kaplan Meadows Sanctuary
- Channing Daughters Winery
- Victoria's Secret
- Riverhead Vacations
- Flanders Vacations
- Southold Vacations
- Meschutt Beach
- Mattebella Vineyards
- Shinnecock Hills Golf Course
- Pugliese Vineyards
- South Fork Natural History Museum and Nature Center
- East Hampton Main Beach
- Sagaponack Vacations
- Sag Harbor Vacations
- East Hampton Vacations
- Amelia Cottage Museum
- Hampton Bays Vacations
- Railroad Museum of Long Island
- Hamptons Vacations
- Sparkling Pointe
- Duck Walk Vineyards
- Shinnecock Nation Cultural Center and Museum
- Southampton Vacations
- Fishers Island Vacations
- Peconic Bay Winery
- Orient Vacations
- Suffolk Theater
- Longhouse Reserve
- Wolffer Estates Vineyard
- Kontokosta Winery
