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.
Studio 6 Suites Pocomoke City, MD

Studio 6 Suites Pocomoke City, MD

2 out of 5
Price was $673, price is now $624 per person
$624
per person
Feb 26 - Mar 2
found 13 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
Free self parking is available and the motel's front desk is staffed around-the-clock. WiFi in public areas is free. A garden is also provided.
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $877, price is now $760 per person
$760
per person
Feb 26 - Mar 2
found 13 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) 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.
Boardwalk One

Boardwalk One

3 out of 5
Downtown Ocean City
Price was $726, price is now $647 per person
$647
per person
Feb 26 - Mar 2
found 13 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
This aparthotel features a seasonal outdoor pool and a rooftop terrace. Guests will appreciate free perks like free self parking and WiFi in public areas. Dry cleaning and laundry facilities are also provided.
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
North Ocean City
Price was $904, price is now $832 per person
$832
per person
Feb 26 - Mar 2
found 13 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) 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.
Cypress River Inn & Spa

Cypress River Inn & Spa

5 out of 5
Price was $1,073, price is now $996 per person
$996
per person
Feb 26 - Mar 2
found 13 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
A restaurant, free self parking, and a garden are among this bed & breakfast's amenities. WiFi in public areas is free. A snack bar/deli, a communal living room, and a picnic area are also on offer.

Top Smith Island hotels deals

Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart

Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart

Smith Island MD
$273 nightly
The price is $289 total per night
$289 total
Jan 5 - Jan 6, 2026
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
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

Smith Island MD
Get rates
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Blue Anchor Cottage at Smith Island MD Quaint & Charming Beach Cottage

Blue Anchor Cottage at Smith Island MD Quaint & Charming Beach Cottage

Smith Island MD
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This vacation home 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
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
$85 nightly
The price is $96 total per night
$96 total
Jan 7 - Jan 8, 2026
Total with 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
Near Chincoteague & Assateague Island Charming 2-bedroom cottage

Near Chincoteague & Assateague Island Charming 2-bedroom cottage

Saxis VA
Get rates
This cottage featured 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

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 $624, 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