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
Save 100% on your flight
Price was $1,536, price is now $1,037 per person
$1,037
per person
Jul 3 - Jul 8
found 2 hours ago
Roundtrip 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.
Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Save 100% on your flight
Price was $1,997, price is now $1,255 per person
$1,255
per person
Jul 3 - Jul 8
found 2 hours ago
Roundtrip flight included
Boston (BOS) 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.
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
North Ocean City
Save 100% on your flight
Price was $1,502, price is now $1,103 per person
$1,103
per person
Jul 3 - Jul 8
found 1 hour ago
Roundtrip flight included
Boston (BOS) 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.
The Surf Shanty Motel

The Surf Shanty Motel

2.5 out of 5
Price was $1,700, price is now $1,265 per person
$1,265
per person
Jul 5 - Jul 11
found 20 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
This motel features 20 beach bars and express check-out. Take advantage of the free self parking.
Holiday Inn & Suites Ocean City by IHG

Holiday Inn & Suites Ocean City by IHG

3 out of 5
Downtown Ocean City
Save 100% on your flight
Price was $1,960, price is now $1,548 per person
$1,548
per person
Jul 3 - Jul 8
found 1 hour ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. You'll appreciate the 24-hour gym, poolside bar, and coffee shop.

Top Smith Island hotels deals

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
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
Summer is almost here on Smith Island! Get ready for a great season on the Bay

Summer is almost here on Smith Island! Get ready for a great season on the Bay

Smith Island MD
$265 nightly
The price is $293 total per night
$293 total
May 31 - Jun 1
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
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
$102 nightly
The price is $115 total per night
$115 total
Jun 14 - Jun 15
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
Get rates
This vacation home features a garden, 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

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 $1,037, 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.