Silver Beach Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Silver Beach

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

Night Hotel Broadway

Manhattan
Save 100% on your flight
CA $823
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
7.6/10 Good! (3,584 reviews)
With very few hotel choices in the very upper west side, we gave this one a second chance. Typical small, dank rooms, but a nice lobby and Great staff. Our toilet was nonfunctioning, but since it was the middle of the night we dealt with it. No price break was offered.

Reviewed on Sep 19, 2026

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

Manhattan
Save 100% on your flight
CA $2,210
per person
Nov 12 - Nov 15
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (702 reviews)
Lotte New York Palace

Lotte New York Palace

Manhattan
Save 100% on your flight
CA $1,237
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (2,230 reviews)
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

Manhattan
Save 100% on your flight
CA $1,248
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (3,331 reviews)
My stay was very good! The room was clean and comfortable, and the location is perfect - very close to Penn Station and 7th Ave. The staff was friendly and helpful. I would definitely recommend this hotel and I will come back again!

Reviewed on Sep 19, 2026

Hotel St. James

Hotel St. James

Manhattan
Save 100% on your flight
CA $1,328
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (7,930 reviews)

Where to stay in Silver Beach

Find the best Silver Beach areas and neighborhoods for the activities you enjoy most. Learn more about Silver Beach
A beach with a wooden sign that reads "Please take off your shoes!"

Menantic Creek

If you're looking for some top things to see and do in Menantic Creek and surrounding area, you can visit Shelter Island Historical Society and Sunset Beach.

A pebble beach with calm water, a distant bridge, and a forested island.

Coecles Harbor

When in Coecles Harbor, you can plan a visit to Shelter Island Historical Society and Mashomack Preserve, some noteworthy sights in the nearby area.

A calm lake with reflections of clouds, surrounded by trees and a distant structure.

Hay Beach

Hay Beach might not have many top sights, but Greenport Carousel and Greenport Harbor Brewing Company are two attractions nearby that you can check out.

An aerial view of a large estate surrounded by water, featuring a prominent mansion, rocky shorelines, and a small island with a lighthouse.

Shorewood

While there might not be top attractions in Shorewood, you can explore the larger area and discover places like Mashomack Preserve and Shelter Island Historical Society.

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Montclair Colony

While Montclair Colony isn't home to many top sights, Sunset Beach and Crescent Beach are some notable places to visit nearby.

Silver Beach Hotel Deals

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
CA $114
CA $131 total
Sep 22 - Sep 23
includes taxes & fees
8/10 Very good! (1,005 reviews)
"Nothing fancy, but clean and nice!"

Reviewed on Sep 19, 2026

Pier Blue Inn Old Saybrook - Essex
Water's Edge Resort & Spa

Water's Edge Resort & Spa

1525 Boston Post Road Westbrook CT
CA $251
CA $312 total
Oct 7 - Oct 8
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"It was the perfect getaway- close to home. The property was beautiful, clean and peaceful. The beach could have been cleaner, but overall we loved our stay. The food served in their variety of restaurants was delicious. We will definitely return."

Reviewed on Sep 15, 2026

Water's Edge Resort & Spa
The Atlantic Hotel

The Atlantic Hotel

1655 County Road 39 Southampton NY
CA $167
CA $226 total
Oct 1 - Oct 2
includes taxes & fees
7.2/10 Good! (1,001 reviews)
"Bed, floor not very clean; Room… walls, furniture, doors cracked, broken, chipped. Walking from lot to back of bldg where room was located, there was no exterior light so felt dangerous. Can hear every footstep from room above so impossible to sleep when people were still walking around middle of ..."

Reviewed on Sep 18, 2026

The Atlantic Hotel
See all 4,021 properties in Silver Beach
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.

Frequently asked questions

How much does a Silver Beach vacation package cost?
Explore the best of Silver Beach from just CA $823. Choose from a wonderful selection of flights, rental cars and hotels to suit your travel style. You can score even better deals when you add a few experiences or tours to your package.
How do I get a cheap travel package to Silver Beach?
Booking a flight and hotel together with Expedia won't just save you time — it'll save you money too. A Silver Beach vacation package makes it easy to put together your ideal trip. With more than 550 airlines around the world to choose from, finding flights that suit your busy schedule won't be a problem. On top of that, we have over 1,000,000 properties globally to take your pick of. Now that's choice! Whatever your budget, Expedia puts more of the world within your reach.
Where should I stay in Silver Beach?
A vacation in Silver Beach wouldn't be complete without checking out Shell Beach, Shelter Island Historical Society and Wades Beach. Spend your evenings near these popular attractions and make sightseeing simple.
What are the top hotels in Silver Beach?
Lock in a room at Lovely Shelter Island Cottage With Panoramic Bay Views. It's one of the neighborhood's most in-demand hotels. Another top option in Silver Beach is Views - Views - Views Of Beautiful Peconic Bay. Tastefully Renovated 1929 Cape.
How far in advance should I book my Silver Beach vacation?
It's hard to pick the perfect time for airfares, but we normally say the earlier, the better. Plenty of international journeys on Expedia become available to compare up to a year in advance. If you're unable to do so, don't despair. Cheap prices appear from time to time within a few weeks of departure dates.
What does an Expedia Silver Beach travel package include?
Choose from any combination of rental cars, flights and hotels. Once you've made your booking, you can add experiences and activities. Want to pick your fare class? That's also possible. The choice is all yours when it comes to planning your dream Silver Beach getaway.
What should I know before booking a Silver Beach travel package?
You'll save big with an Expedia travel package. Combine your flights, rental cars and hotels and land fantastic discounts. Hotels aren't your only choice, however. We've got beachfront villas, cabins in the mountains and even castles and houseboats!
Can I choose my airline with a Silver Beach Expedia vacation package?
You can, and with more than 550 airlines to choose from globally, you're spoiled for choice. Search the available options and see which airline suits your budget and needs.
If I'm not able to travel, can I cancel my Silver Beach vacation package?
It's impossible to predict what tomorrow might bring, so it's good to know that you can cancel or change your Silver Beach vacation package. If you booked in the last 24 hours, you may be entitled to a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal to learn more.

Things to do

Public Schooner Sail in Greenport

Sunday Brunch Sail in Greenport

CA $242
per adult
Sunday Brunch Sail in Greenport
See all activities in Shelter Island
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.