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.
Ocean Terrace Family Apartments

Ocean Terrace Family Apartments

3 out of 5
Downtown Ocean City
Price was $686, price is now $606 per person
$606
per person
May 23 - May 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Free WiFi in public areas is available at this apartment. Take advantage of the free self parking.
Miramar Condominiums

Miramar Condominiums

2 out of 5
Downtown Ocean City
Price was $1,422, price is now $1,205 per person
$1,205
per person
May 23 - May 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $795, price is now $682 per person
$682
per person
May 23 - May 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Eden Roc Ocean Front

Eden Roc Ocean Front

2 out of 5
Downtown Ocean City
Price was $1,307, price is now $1,140 per person
$1,140
per person
Jun 15 - Jun 20
found 18 hours ago
Roundtrip non-stop flight included
Syracuse (SYR) to Salisbury (SBY)
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A seasonal outdoor pool is also provided.
Americana Motor Inn

Americana Motor Inn

2.5 out of 5
Downtown Ocean City
Price was $805, price is now $707 per person
$707
per person
Jun 1 - Jun 4
found 24 hours ago
Roundtrip non-stop flight included
Syracuse (SYR) to Salisbury (SBY)
A restaurant, free self parking, and a 24-hour front desk are among this hotel's amenities. WiFi in public areas is free. Free newspapers are provided for your convenience.

Top Smith Island hotels deals

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

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

Smith Island MD
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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

Smith Island MD
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This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Historic home on Smith Island w/ dock!

Historic home on Smith Island w/ dock!

Smith Island MD
$272 nightly
The price is $288 total per night
$288 total
Mar 31 - Apr 1
Total with taxes and fees
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
Apr 11 - Apr 12
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
Private Pier, Main+Guest House | Luxe Waterfront Home | Bay Estate by AvantStay

Private Pier, Main+Guest House | Luxe Waterfront Home | Bay Estate by AvantStay

Dameron MD
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This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay

Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay

Scotland MD
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Limo/town car service, a garden, and a picnic area are available at this cottage. There's fun for all ages with a playground and an arcade/game room, and childcare is an added bonus. Laundry facilities and barbecue grills are also provided.
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.

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

Tylerton County Dock

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

Tylerton County Dock

Horse Hammock

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

Horse Hammock

Frequently asked questions

How much are vacation packages to Smith Island?
With vacation packages being sold for only $606, 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

Female kayaking at Smith Island in Maryland.