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.
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3.5 out of 5
Price was $660, price is now $575 per person
$575
per person
Nov 25 - Nov 29
found 1 hour ago
Roundtrip flight included
Orlando (MCO) to Salisbury (SBY)
A golf course, 2 restaurants, and a 24-hour gym are all featured at this smoke-free lodge. Dine at the beachfront restaurant and relax with sun loungers. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas.
Microtel Inn & Suites by Wyndham Salisbury

Microtel Inn & Suites by Wyndham Salisbury

2 out of 5
Price was $1,099, price is now $1,099 per person
$1,099
per person
Oct 20 - Oct 27
found 19 hours ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Salisbury (SBY)
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Top Smith Island hotels deals

Pet-Friendly Smith Island Cottage w/ Golf Cart!

Pet-Friendly Smith Island Cottage w/ Golf Cart!

Ewell MD
Get rates
This cottage features laundry facilities.
Kitchen
Washer
Historic home on Smith Island w/ dock!

Historic home on Smith Island w/ dock!

Smith Island MD
Get rates
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Charming 2 Bedroom house in beautiful Smith Island Pet-Friendly Golf Cart

Charming 2 Bedroom house in beautiful Smith Island Pet-Friendly Golf Cart

Smith Island MD
Get rates
This vacation home features laundry facilities.
Kitchen
Washer
Spacious 5-bedroom house with WiFi, AC and private deck on charming Smith Island

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

Smith Island MD
Get rates
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
The end of summer is here on Smith Island! Come out for some peace and quiet!

The end of summer is here on Smith Island! Come out for some peace and quiet!

Smith Island MD
$297 nightly
The price is $328 total per night
$328 total
Oct 16 - Oct 17
Total with 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
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK & golf cart rental

IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK & golf cart rental

Smith Island MD
Get rates
This cottage features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
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.

Stay near popular Smith Island attractions

Smith Island

9.0/10 (21 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.
See properties

Frequently asked questions

How much are vacation packages to Smith Island?
With vacation packages being sold for only $575, 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

A person in a kayak on a calm body of water during sunset.