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.
OCHG VIRGINIA LEE

OCHG VIRGINIA LEE

2 out of 5
Downtown Ocean City
Price was $1,135, price is now $1,031 per person
$1,031
per person
Dec 15 - Dec 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
Free WiFi in public areas is available at this condo. Take advantage of the free self parking.
Bay Estate Luxe Waterfront Home w/ Private Pier, Main+guest House, Bay Views

Bay Estate Luxe Waterfront Home w/ Private Pier, Main+guest House, Bay Views

3 out of 5
Save 100% on your flight
Price was $3,284, price is now $2,387 per person
$2,387
per person
Dec 5 - Dec 8
found 15 hours ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. Barbecue grills are provided for your convenience.
Beach Walk

Beach Walk

2 out of 5
Downtown Ocean City
Price was $2,425, price is now $1,952 per person
$1,952
per person
Dec 15 - Dec 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
This hotel features free self parking and express check-in. Express check-out is also provided.
OCHG Ocean Block 7-11

OCHG Ocean Block 7-11

3 out of 5
Downtown Ocean City
Price was $1,217, price is now $1,089 per person
$1,089
per person
Dec 15 - Dec 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
Free WiFi in public areas is available at this condo. Take advantage of the free self parking.
Bay Club Resort by Coolvacay

Bay Club Resort by Coolvacay

3 out of 5
Midtown Ocean City
Price was $1,187, price is now $1,063 per person
$1,063
per person
Dec 15 - Dec 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
An indoor pool is featured at this condo resort, along with laundry facilities. 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!

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This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
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

$326 nightly
The price is $346 total per night
$346 total
Oct 7 - Oct 8
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

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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
Oct 18 - Oct 19
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
Swanendele Inn at St. Mary's Maryland

Swanendele Inn at St. Mary's Maryland

5 out of 5
49946 Airedele Rd, Ridge, MD
$305 nightly
The price is $339 total per night
$339 total
Oct 6 - Oct 7
Total with taxes and fees
This luxury bed & breakfast's private beach and marina are among the highlights. Spend a day at the beach kayaking, or relax with sun loungers and beach umbrellas. There's no skimping on freebies - guests receive free cooked-to-order breakfast, free WiFi, and free self parking.
On private beach
Breakfast included
Cottage near the Bay

Cottage near the Bay

$176 nightly
The price is $187 total per night
$187 total
Oct 16 - Oct 17
Total with taxes and fees
This vacation home featured laundry facilities and barbecue grills.
Kitchen
Dryer
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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

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 $1,031, 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