Book Hotels in Smith Island, MD

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Top Smith Island hotels

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

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Opens in a new windowSpacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 1 Min Walk to Sand

A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 1 Min Walk to Sand

Scotland MD
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 ...
the house was perfect! Jocelyn was a terrific host. She provided a welcome basket with cookies, materials for Smores. there are games, activities, beach toys, even bikes! The kitchen and entire house are well-appointed with absolutely everything you mighty need for a nice stay. Adorable interior ...

Reviewed on Oct 19, 2025

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Opens in a new windowA Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 1 Min Walk to Sand
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
$296 nightly
The price is $314 total per night from Nov 21 to Nov 22
$314 total
Nov 21 - Nov 22
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.
Excellent property, excellent host. This is a very well-appointed property located very close to the ferry dock. Golf cart, bikes, and kayaks were in great shape. Chris could not have been a more responsive or helpful host.

Reviewed on Oct 28, 2025

Opens in a new windowKayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart
Swanendele Inn at St. Mary's Maryland

Swanendele Inn at St. Mary's Maryland

5 out of 5
49946 Airedele Rd Ridge MD
$610 nightly
The price is $677 total per night from Nov 21 to Nov 22
$677 total
Nov 21 - Nov 22
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. ...
Very beautiful clean Inn
Very beautiful Inn. The rooms are very clean and quiet. There are lots of sitting areas on the property, and a pier that you can walk out on to view the bay. The breakfast was wonderful. There is a small bar downstairs, but we weren't sure if it was in operation. The check-in was a bit awkward. Hotels.com ...

Reviewed on Sep 15, 2025

Opens in a new windowSwanendele Inn at St. Mary's Maryland
Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!

Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!

Reedville VA
This vacation home features a garden, laundry facilities, and barbecue grills.
Beautiful house with great views, fantastic amenities.

Reviewed on Nov 10, 2025

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Opens in a new windowSecluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!
Bay Front Small Contemporary

Bay Front Small Contemporary

Reedville VA
This vacation home featured laundry facilities and barbecue grills.
Overall, we had a good time at Bay Front especially the front porch and it’s view. The living space is a little smaller than we anticipated but it wasn’t bad for us. We enjoyed the quiet of the area it helped you to really relax. The property is a little off the beaten path so the description may ...

Reviewed on Oct 28, 2025

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Opens in a new windowBay Front Small Contemporary
Historic home on Smith Island w/ dock!

Historic home on Smith Island w/ dock!

Smith Island MD
This vacation home features a garden, laundry facilities, and barbecue grills.
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

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Opens in a new windowHistoric home on Smith Island w/ dock!
Near Chincoteague & Assateague Island Charming 2-bedroom cottage

Near Chincoteague & Assateague Island Charming 2-bedroom cottage

Saxis VA
This cottage featured laundry facilities and barbecue grills.
Lovely, small but cozy, great place to bond and enjoy good food and drink.

Reviewed on Oct 13, 2025

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Opens in a new windowNear Chincoteague & Assateague Island Charming 2-bedroom cottage
Rodeway Inn at Somers Cove Marina

Rodeway Inn at Somers Cove Marina

2 out of 5
700 Norris Harbor Dr Crisfield MD
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $96 total per night from Dec 3 to Dec 4
$96 total
Dec 3 - Dec 4
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 ...
Pleasantly surprised
We came for one night and was pleasantly surprised at how quiet it was and clean perfect for a one night stay

Reviewed on Oct 13, 2025

Opens in a new windowRodeway Inn at Somers Cove Marina
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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.

Frequently asked questions

What are the top kid-friendly hotels in Smith Island?
Family getaways are where the best memories are made, but traveling with youngsters can be challenging. These kid-friendly Smith Island hotels offer perks designed to keep travelers of all ages comfortable and happy: Blue Heron Cottage On Smiths Island will help make your getaway the best one yet. It features plenty of nice touches, such as a barbecue grill and a fridge. Alternatively, spend your Smith Island break at IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK. Make the most of a playground, cycling and more here.
Where can I find cheap hotels in Smith Island?
At Travelocity you'll find really nice hotels in Smith Island at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Smith Island rather than in Smith Island. We may find you even better rates, too.
How do I find the best Smith Island hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Smith Island then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Smith Island?
The cheapest hotel in Smith Island is $96. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Smith Island?
There are 192 hotels in Smith Island on Travelocity.
What are the best hotels in Smith Island?
Smith Island has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Smith Island for you!
When is the best time to visit Smith Island?
If you want the joy of a fun-filled trip in peak season, visit Smith Island during May, June and July. If you'd prefer the peace of off-season, book a stay during quieter months, such as November, December and January.
When is the cheapest time to stay in Smith Island?
Based on historic data is usually the cheapest month to visit Smith Island. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Smith Island?
There are multiple hotels in Smith Island that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Smith Island. We have plenty of kid-friendly hotels in Smith Island to choose from on Travelocity!
Why book a hotel in Smith Island through Travelocity?
Because we have the top hotels in Smith Island! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Smith Island on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Smith Island hotel reviews by fellow wanderers

Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!

Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!

5 out of 5
Posted 10 days ago
Travelocity Verified Review
"Beautiful house with great views, fantastic amenities. "
A verified traveler stayed at Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!
Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!

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