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.
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $195, price is now $156 per person
$156
per person
Dec 4 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 WiFi.
Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Price was $831, price is now $679 per person
$679
per person
Dec 5 - Dec 12
found 15 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Salisbury (SBY)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
Plantation Lakes Townhouse

Plantation Lakes Townhouse

2 out of 5
Save 100% on your flight
Price was $6,086, price is now $5,268 per person
$5,268
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Salisbury (SBY)
A seasonal outdoor pool is available at this vacation home. Take advantage of the free self parking.
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
North Ocean City
Price was $912, price is now $793 per person
$793
per person
Dec 5 - Dec 12
found 15 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Salisbury (SBY)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Dine at the beachfront restaurant and relax with beach umbrellas. Family-friendly amenities include an arcade/game room and kid-friendly dining, along with volleyball.
Wingate by Wyndham Salisbury MD Airport North

Wingate by Wyndham Salisbury MD Airport North

3 out of 5
Price was $798, price is now $700 per person
$700
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Salisbury (SBY)
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-out. Enjoy the outdoor pool 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
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This cottage features laundry facilities.
Kitchen
Washer
Historic home on Smith Island w/ dock!

Historic home on Smith Island w/ dock!

Smith Island MD
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This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
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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
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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
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This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Come out and enjoy Autumn at the HH Ranch on Smith Island.

Come out and enjoy Autumn at the HH Ranch on Smith Island.

Smith Island MD
$303 nightly
The price is $334 total per night
$334 total
Oct 17 - Oct 18
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
Water Front 1 bedroom house on tranquil Smith Island

Water Front 1 bedroom house on tranquil Smith Island

Smith Island MD
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This vacation home features laundry facilities.
Kitchen
Washer
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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.

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.
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Frequently asked questions

How much are vacation packages to Smith Island?
With vacation packages being sold for only $156, 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.