Deals on vacations and trips to Smith Island

Save when you book Smith Island package deals

Choose two or more items and save on your trip:

Smith Island flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Sahara Motel

Sahara Motel

2.5 out of 5
Downtown Ocean City
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Salisbury (SBY)
A seasonal outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. Staff at the 24-hour front desk can provide around-the-clock assistance.
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) 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.
The Americana Hotel

The Americana Hotel

2.5 out of 5
Downtown Ocean City
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) 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.
Miramar Condominiums

Miramar Condominiums

2 out of 5
Downtown Ocean City
Save 100% on your flight
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Salisbury (SBY)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. Staff at the 24-hour front desk can provide around-the-clock assistance.
Ocean Terrace Family Apartments

Ocean Terrace Family Apartments

3 out of 5
Downtown Ocean City
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Salisbury (SBY)
Free WiFi in public areas is available at this apartment. Take advantage of the free self parking.

Top Smith Island hotels deals

Historic home on Smith Island w/ dock!

Historic home on Smith Island w/ dock!

Get rates
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!

Get rates
This cottage features laundry facilities.
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

Get rates
This cottage features a garden, laundry facilities, and barbecue grills.
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

Get rates
This vacation home 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

$326 nightly
The price is $346 total per night
$346 total
Aug 18 - Aug 19
Total includes taxes and fees
A gym is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Kitchen
Washer
Rodeway Inn at Somers Cove Marina

Rodeway Inn at Somers Cove Marina

2 out of 5
700 Norris Harbor Dr, Crisfield, MD
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $106 total per night
$106 total
Sep 1 - Sep 2
Total includes taxes and fees
An outdoor pool, free self parking, and barbecue grills are featured at this motel. WiFi in public areas is free. A garden and a picnic area are also provided.
Pool
Pet friendly
Don't see what you're looking for?
See all available properties in Smith Island
View all properties
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 $688, 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