Title: Smith Island Vacation Packages 2026 from $430 | Expedia.com

[Hotels in Smith Island](https://expedia.com/Smith-Island-Hotels.d553248634999169749.Travel-Guide-Hotels)[Vacation Rentals in Smith Island](https://expedia.com/Smith-Island-Vacation-Rentals.d553248634999169749.Travel-Guide-VacationRentals)[Flights to Smith Island](https://expedia.com/Cheap-Flights-To-Smith-Island.d553248634999169749.Travel-Guide-Flights)[Car Rentals in Smith Island](https://expedia.com/Car-Rentals-In-Smith-Island.d553248634999169749.Car-Rental-Guide)

![](https://images.trvl-media.com/place/553248634999169749/bba65392-3549-4ca0-acfd-921c814971e7.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Smith Island Vacations from $430

## Book a Hotel + Flight or Car together to unlock savings

## The Latest Smith Island vacation packages

Price found within the past 48 hours. Click for updated prices.

![The Surf Shanty Motel](https://images.trvl-media.com/lodging/79000000/78480000/78475200/78475169/629d609a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Surf Shanty Motel

$430

per person

May 14 - May 17

found 18 hours ago

Roundtrip flight included

New York (NYC) to Salisbury (SBY)

9.8/10 Exceptional! (310 reviews)

The hotel was clean and the staff were very helpful. The only negative was there was no closet to hang our dresses. We came for a wedding and it would have been nice to have somewhere to hang out gowns. Other than than that we enjoyed our stay.

Reviewed on Dec 16, 2025

![Fenwick Shores, Tapestry Collection by Hilton](https://images.trvl-media.com/lodging/9000000/8310000/8308900/8308889/83ce2997_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Fenwick Shores, Tapestry Collection by Hilton

$585

per person

May 14 - May 17

found 18 hours ago

Roundtrip flight included

New York (NYC) to Salisbury (SBY)

9.4/10 Exceptional! (734 reviews)

Parking was awesome and Bar/Food service was very good

Reviewed on Apr 2, 2026

![Grand Hotel Ocean City Oceanfront](https://images.trvl-media.com/lodging/1000000/810000/800800/800771/7811430e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Grand Hotel Ocean City Oceanfront

Downtown Ocean City

$804

per person

May 29 - Jun 2

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Salisbury (SBY)

9/10 Wonderful! (3,461 reviews)

The gym was very small. The shower needs a removable handle. The pressure could have been stronger as well. Instead of a straight shower bar, it needs the curved ahower bar so that the shower curtain does not touch you. Had to pay extra to park in the parking lot associated with the hotel, such a rip-off!! $10 plus taxes

Reviewed on Apr 7, 2026

![Gold Leaf Hotel of Dewey - Rehoboth Beach](https://images.trvl-media.com/lodging/18000000/17450000/17444200/17444119/5c1ffb2b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Gold Leaf Hotel of Dewey - Rehoboth Beach

$496

per person

May 14 - May 17

found 18 hours ago

Roundtrip flight included

New York (NYC) to Salisbury (SBY)

8.8/10 Excellent! (1,002 reviews)

This is a solid, not fancy place almost directly on the beach. It is less than 5 minute walk to the beach and to several restaurants. The hotel is showing its age but is well maintained. The beds are comfortabl. The rooms are a good size. Parking in the ramp near the room was a nice feature. The shower wasnt great, both in terms of water pressure/ shower head and also water splashing out. It was just what we needed for the night we were passing through. Great value.

Reviewed on Apr 5, 2026

![Ocean Terrace Family Apartments](https://images.trvl-media.com/lodging/91000000/90730000/90727900/90727842/c458462b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Ocean Terrace Family Apartments

Downtown Ocean City

$1,362

per person

Jul 3 - Jul 5

found 1 hour ago

Roundtrip non-stop flight included

New York (NYC) to Salisbury (SBY)

8/10 Very Good! (31 reviews)

The unit was outdated, small, and had mismatched and old furniture. The shower in one of our bathrooms wouldn’t drain. The oven did not work. There was only one television. Concerns couldn’t be communicated because the staff hardly spoke English (although they were very nice). The unit was in a really nice location - 1.5 blocks from the boardwalk and beach. We liked the outside showers.

Reviewed on Aug 9, 2025

Don't see what you're looking for?

See all available trips from Columbus to Smith Island

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-05-07/2026-05-14/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=null&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

### Discover the most popular places to visit in Smith Island

#### Smith Island

4.5/5(13 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. 

[](https://expedia.com/Smith-Island-Smith-Island.d553248621532662078.Vacation-Attraction)

## Smith Island Hotel Deals

![Historic home on Smith Island w/ dock!](https://images.trvl-media.com/lodging/64000000/63950000/63942900/63942827/f202aa27_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Historic home on Smith Island w/ dock!

 Smith Island MD

9.6/10 Exceptional! (46 reviews)

We enjoyed ourselves besides the weather that turned bad, fall is not the best time to visit Smith Island, everything was operating on limited hours.

Reviewed on Oct 3, 2025

[Get rates](https://expedia.com/Hotel-Search?startDate=4%2F21%2F2026&endDate=4%2F22%2F2026&selected=63942827&PinnedHotelID=63942827&HadPinnedHotel=true&regionId=553248634999169749)

[](https://expedia.com/Hotel-Search?startDate=4%2F21%2F2026&endDate=4%2F22%2F2026&selected=63942827&PinnedHotelID=63942827&HadPinnedHotel=true&regionId=553248634999169749)

![IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK](https://images.trvl-media.com/lodging/72000000/71470000/71467900/71467811/024eac30_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

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

 Smith Island MD

10/10 Exceptional! (18 reviews)

The Jazzy 6 loved the accommo- dations and the kitchen was great. Stocked with seasonings, coffee and tea. Marykim was a wonderful hostess. She had our golf cart delivered to Idol Hour and our Smith Island Strawberry cake was in the refrigerator waiting for us. We loved Idol Hour and would stay again. ...

Reviewed on Aug 18, 2025

[Get rates](https://expedia.com/Hotel-Search?startDate=4%2F21%2F2026&endDate=4%2F22%2F2026&selected=71467811&PinnedHotelID=71467811&HadPinnedHotel=true&regionId=553248634999169749)

[](https://expedia.com/Hotel-Search?startDate=4%2F21%2F2026&endDate=4%2F22%2F2026&selected=71467811&PinnedHotelID=71467811&HadPinnedHotel=true&regionId=553248634999169749)

![Spacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island](https://images.trvl-media.com/lodging/111000000/110150000/110145700/110145636/e23353a2_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Spacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island

 Smith Island MD

10/10 Exceptional! (1 review)

Amazing Adventure

Amazing adventure! Peaceful! Beautiful! Privacy! Gourmet Kitchen! The house is set back from the neighborhood on a large lot. The decks are new and comfortably furnished. We cooked breakfast and dinner for 3 days and the well-equipped kitchen was perfect. Our days started and ended with gourmet meals, ...

Reviewed on Jun 18, 2025

[Get rates](https://expedia.com/Hotel-Search?startDate=4%2F21%2F2026&endDate=4%2F22%2F2026&selected=110145636&PinnedHotelID=110145636&HadPinnedHotel=true&regionId=553248634999169749)

[](https://expedia.com/Hotel-Search?startDate=4%2F21%2F2026&endDate=4%2F22%2F2026&selected=110145636&PinnedHotelID=110145636&HadPinnedHotel=true&regionId=553248634999169749)

[See all 201 properties in Smith Island](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=4%2F8%2F2026&endDate=4%2F9%2F2026&regionId=553248634999169749)

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.

## Find the Best Smith Island Vacation Packages

## Smith Island Essential Information

| Language   | English                                                                                                                                                                                                                                            |
| ---------- | -------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- |
| Currency   | U.S dollars                                                                                                                                                                                                                                        |
| Top Sights | [J. Millard Tawes Museum](https://www.expedia.com/J-Millard-Tawes-Museum-Crisfield.d553248621592397532.Vacation-Attraction) and [Somers Cove Marina](https://www.expedia.com/Somers-Cove-Marina-Crisfield.d553248621532662315.Vacation-Attraction) |

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## Frequently asked questions

### How much does a Smith Island vacation package cost?

### What are the cheapest months to go to Smith Island?

### How many days is enough for Smith Island?

### How to find the best Smith Island package deals?

### Is it cheaper to book a Smith Island vacation as a package?

### When to book a vacation package to Smith Island?

### Does Expedia offer Book Now, Pay Later Smith Island vacation packages?

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.