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
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, 60 Second Walk to Beach

A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach

Scotland
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 ...
"This property could not have been cuter and Jocelyn has thought of everything you could possibly need. The kids play shed kept them busy for hours and the backyard was an oasis!"

Reviewed on Sep 21, 2025

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Opens in a new windowA Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach
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 from Oct 7 to Oct 8
$339 total
Oct 7 - Oct 8
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
Historic home on Smith Island w/ dock!

Historic home on Smith Island w/ dock!

Smith Island
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!
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
$326 nightly
The price is $346 total per night from Oct 7 to Oct 8
$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.
"Such a lovely, cozy little house. Right in town. We could walk to restaurants and the bakery. We really enjoyed talking with the islanders and the walk out to Rhodes Point was beautiful."

Reviewed on Sep 20, 2025

Opens in a new windowKayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart
Private infinity pool, plus your own dock, kayaks, and bikes on the waterfront!

Private infinity pool, plus your own dock, kayaks, and bikes on the waterfront!

Reedville
An outdoor pool is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
"Stay was great, host was very responsive! Cabbing was great fishing we weren’t as lucky but we would be back!"

Reviewed on Aug 23, 2025

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Opens in a new windowPrivate infinity pool, plus your own dock, kayaks, and bikes on the waterfront!
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 Oct 19 to Oct 20
$96 total
Oct 19 - Oct 20
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 ...
"I have no pets"

Reviewed on Sep 28, 2025

Opens in a new windowRodeway Inn at Somers Cove Marina
Cottage near the Bay

Cottage near the Bay

Crisfield
$176 nightly
The price is $187 total per night from Oct 16 to Oct 17
$187 total
Oct 16 - Oct 17
Total with taxes and fees
This vacation home featured laundry facilities and barbecue grills.
"Great little place"

Reviewed on Sep 28, 2025

Opens in a new windowCottage near the Bay
Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville

Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville

2 out of 5
Reedville
$194 nightly
The price is $208 total per night from Oct 19 to Oct 20
$208 total
Oct 19 - Oct 20
Total with taxes and fees
This vacation home featured laundry facilities and barbecue grills.
"Nice place"

Reviewed on Jul 31, 2025

Opens in a new windowCharming 3-bedroom house with WiFi, AC& heat in peaceful Reedville
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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 189 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

BEACH COTTAGE BY THE SEA....

BEACH COTTAGE BY THE SEA....

5 out of 5
Posted 7 days ago
Travelocity Verified Review
"Beautiful scene. Sunrise on the beach is perfect. Loved the low waves. Was easy to swim. The home was so cute! They were FULLY stocked. Anything that you think you may need and it’s there. The bed was squishy comfy. Even when we stayed inside, we had a gorgeous view from the sunroom. The neighbors were super friendly. The host was very responsive and extremely nice! Will definitely return to this little paradise!"
A verified traveler stayed at BEACH COTTAGE BY THE SEA....
BEACH COTTAGE BY THE SEA....

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