Deals on vacations and trips to Smith Island

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Smith Island flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Beach Walk

Beach Walk

2 out of 5
Downtown Ocean City
Save 100% on your flight
per person
Aug 9 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
This hotel features free self parking and express check-in. Express check-out is also provided.
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Save 100% on your flight
per person
Aug 9 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
This hotel features 4 restaurants, an outdoor pool, and an indoor pool. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the gym and perks like free self parking and free WiFi.
Ocean Terrace Family Apartments

Ocean Terrace Family Apartments

3 out of 5
Downtown Ocean City
Save 100% on your flight
per person
Aug 9 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
Free WiFi in public areas is available at this apartment. Take advantage of the free self parking.
Club Ocean Villas II

Club Ocean Villas II

3.5 out of 5
North Ocean City
Save 100% on your flight
per person
Aug 9 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
A marina and an indoor pool are featured at this smoke-free apartment. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. Enjoy the hot tub and conveniences like a picnic area and a virtual front desk.
The Americana Hotel

The Americana Hotel

2.5 out of 5
Downtown Ocean City
Save 100% on your flight
per person
Aug 9 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
This hotel features a restaurant and 2 bars/lounges. Enjoy the indoor pool and perks like free WiFi. Self parking and a safe deposit box are also offered on site.

Top Smith Island hotels deals

Historic home on Smith Island w/ dock!

Historic home on Smith Island w/ dock!

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This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Pet-Friendly Smith Island Cottage w/ Golf Cart!

Pet-Friendly Smith Island Cottage w/ Golf Cart!

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This cottage features laundry facilities.
Kitchen
Washer
Blue Heron Cottage On Smith's Island

Blue Heron Cottage On Smith's Island

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This cottage featured laundry facilities and barbecue grills.
Kitchen
Washer
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

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This cottage features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Get away to relax on Smith Island in the Chesapeake Bay with golf cart included

Get away to relax on Smith Island in the Chesapeake Bay with golf cart included

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A gym is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Kitchen
Washer
Spacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island

Spacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island

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This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
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See all available properties in Smith Island
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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.

Popular places to visit

Smith Island

4.5/5(12 reviews)

Commune with nature and explore the great outdoors at Smith Island during your travels in Smith Island. Discover the sunsets in this relaxing area, or seek out the fishing spots.

Smith Island

Horse Hammock

Commune with nature and explore the great outdoors at Horse Hammock during your travels in Smith Island.

Horse Hammock

Tylerton County Dock

Explore the waterfront in Tylerton with a trip to Tylerton County Dock.

Tylerton County Dock

Frequently asked questions

How much are vacation packages to Smith Island?
With vacation packages being sold for only $893, you won't need to blow out the credit card for your getaway to Smith Island. Travelocity is here to help. Bundle flights, hotels and tours into a convenient package and land some fantastic discounts. The more you book, the greater the savings.
Where can I get the best vacation package deals for Smith Island?
You'll discover a tempting selection of Smith Island package deals on Travelocity. With 400 partner airlines and 1,000,000 properties across the globe, putting together your ultimate escape will be a piece of cake.
Why should I book my Smith Island vacation bundle via Travelocity?
The three S's --- savings, support and a stress-free booking --- are just the tip of the iceberg. Enjoy a fulfilling travel experience knowing you can rely on round-the-clock support. With the Travelocity Price Match Guarantee, you can relax knowing you'll always get the best deal available.
Can I save on my Smith Island car rental if I combine it with my hotel or flight?
With a Smith Island vacation package, you can bundle your car, hotel and flight bookings and save a ton. If you want to see the best of this fabulous region, why not make tracks to White House? This well-known sight is 85 mi from Smith Island. With your own set of wheels, you'll be there before you know it.
Which airport is best for Smith Island?
Salisbury - Ocean City Wicomico Regional Airport (SBY), the gateway to Smith Island, is where you'll get off the plane. You'll find it 35 mi northeast of the center of town.
Where should I stay when visiting Smith Island?
If you're after a place to base yourself, check out the Blue Anchor Cottage at Smith Island MD Quaint & Charming Beach Cottage. It's the top pick for many visitors.

Photos of local treasures

Browse Smith Island vacation photos for more inspiration