Smith Island Vacation Rentals from ￥11,717: Search Short-Term Rentals

Q: What are some of the best vacation home rentals in Smith Island?

Historic home on Smith Island w/ dock! : Visitors like this Smith Island vacation home rental. It is located on the waterfront and has a patio, a private yard, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of books.

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Vacation Rentals in Smith Island

"Smith island is lovely! This house was perfectly located and furnished and the owner super helpful."

￥37,911 total

includes taxes & fees

Jul 1 - Jul 2

"We enjoyed our stay. The host was very responsive to our needs and I appreciate her flexible schedule"

￥27,140 total

includes taxes & fees

Jul 6 - Jul 7

￥29,133 total

includes taxes & fees

Jul 7 - Jul 8

"Wonderful property! Great communication!"

￥58,359 total

includes taxes & fees

Jul 28 - Jul 29

"I did do some cooking and did not find a sheet pan."

￥31,679 total

includes taxes & fees

Jul 10 - Jul 11

"Very nice, would definitely come back thanks "

￥76,095 total

includes taxes & fees

Jul 6 - Jul 7

"Great location and nice view"

￥167,737 total

includes taxes & fees

Jul 25 - Jul 26

"Lots to do and very quiet."

￥83,094 total

includes taxes & fees

Jul 17 - Jul 18

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Find out more about Smith Island

Search for holiday rentals in Smith Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Smith Island using one of the methods below:

View our selection of featured holiday rentals in Smith Island
Use the map to find apartments and other holiday homes in the Smith Island neighbourhood you prefer
Enter your travel dates to view the best deals on holiday rentals in Smith Island while they last

Look no further and take a look at our great range of rental properties in Smith Island!

Recent reviews of Smith Island properties

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

5/5 Excellent

"Took my grandson for a weekend trip to Smith Island to celebrate his HS graduation. My daughter, also, accompanied us, since I am a 90 year old "Grammy", and need some assistance. Our cottage was clean, comfortable and had all of our needs. The host, Kim, was extremely attentive, and made our dinner the night we arrived so we could just relax. I would highly recommend Idle Hour as the place to stay on Smith Island. Pat Reynolds, Ellicott City, MD"

A verified traveler stayed at IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

Posted 6 days ago

Waterfront Getaway: Kayaks, Paddle Board, Fishing!

5/5 Excellent

Recommend Again and Again

"This property far exceeded our expectations! Megan’s communication and hospitality were exceptional often responding within minutes of sending questions about the property and surrounding area. She even went out of her way to research resources in the area ahead of our stay. The house was very clean, plenty of dishes and other conveniences to make our stay hassle free and EVERYTHING in the home is labeled with clear instructions and procedures. Our only regret is that we didn’t stay longer! We used the paddle board and kayaks, the crab traps and also visited a nearby nature preserve. Our 4-year-old is already asking when we can come back. They also have plenty of resources for canine friends which was a huge bonus for us with our little Boston Terrier. Would recommend again and again!!"

A verified traveler stayed at Waterfront Getaway: Kayaks, Paddle Board, Fishing!

Posted 6 days ago

Pet-Friendly Smith Island Cottage w/ Golf Cart!

5/5 Excellent

Adorable cottage

"The cottage was very homey, pretty and clean. The furnishings and color scheme have the cottage a wam feel. What was a particularly nice touch was the cute doggie towel on the bench by the front door and doggie bags for clean up. The dog towel came in handy since my dear darling rolled on a rotten duck egg. The host was very friendly and accessible if needed. Will definitely stay there again."

A verified traveler stayed at Pet-Friendly Smith Island Cottage w/ Golf Cart!

Posted 7 days ago

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

5/5 Excellent

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, on the deck, emersed in the salt marsh. We explored the creeks, guts, and islands all around Ewell, Rhodes Point and Tylerton. Rich and Dani helped coordinate a private charter boat to bring our kayaks and gear. Everyone we met was very helpful and kind. Smith Island is a paddler's/adventurer’s paradise. And, if after a long day of exploring you want a comfortable bed, internet, and all the comforts of home this is the spot. Rich and Danis house is the perfect home base for any group Smith Island adventure!"

A verified traveler stayed at Spacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island

Posted 11 days ago

𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻 𝐇𝐀𝐘𝐒 𝐁𝐄𝐀𝐂𝐇 step of your porch into the sand 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘

5/5 Excellent

Swim & crab trip

"We went swimming and also caught 21 blue claw crabs. They were delicious. The kids had a ball. "

A verified traveler stayed at 𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻 𝐇𝐀𝐘𝐒 𝐁𝐄𝐀𝐂𝐇 step of your porch into the sand 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘

Posted 11 days ago

Get away to relax on Smith Island in the Chesapeake Bay with golf cart included

5/5 Excellent

Perfect relaxing weekend

"Visiting with locals, fresh steamed crabs, simply enjoying the quiet island life"

A verified traveler stayed at Get away to relax on Smith Island in the Chesapeake Bay with golf cart included

Posted 2 weeks ago

5/5 Excellent

"Great location, beautiful view! We stayed as two couples for a long weekend, plenty of space. House was very clean and planters outside are gorgeous! We enjoyed relaxing on the deck and made use of the paddle board and the private beach. We also followed our GPS into the subdivision nextdoor and a nice neighbor pointed us in the right direction. Don’t turn left at the subdivision sign. Carry on straight down the long dirt driveway. Once you find it, you’ll be very happy you did!"

A verified traveler stayed at Bay Front Small Contemporary

Posted 2 weeks ago

Frequently asked questions

Can I find vacation rentals in Smith Island?

Yes, you can find vacation rentals close to the most popular attractions in Smith Island, or you can go with a secluded option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals in Smith Island?

Historic home on Smith Island w/ dock!: Visitors like this Smith Island vacation home rental. It is located on the waterfront and has a patio, a private yard, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of books.

How many vacation rentals are there in Smith Island?

With 6 Expedia vacation rentals, you're sure to find just the right place for your Smith Island stay.

What can I see and do in Smith Island?

Smith Island and Horse Hammock are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find Tylerton County Dock and Terrapin Sand Point.

What are vacation rentals like in Smith Island?

Vacation rentals are privately owned properties you can reserve for a short or long stay in Smith Island. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll feel right at home. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for small groups.

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Smith Island Vacation Rentals

Check prices for these dates

Vacation Rentals in Smith Island

Get away to relax on Smith Island in the Chesapeake Bay with golf cart included

Cottage near the Bay

Tangier Escape, great place get away from it all on Deal Island, MD.

Reelin&Relaxin Spacious Farmhouse Reedville, VA Sleeps 8: 3 Bdrm 2 full bathroom

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

Waterfront Getaway: Kayaks, Paddle Board, Fishing!

Kentigern at Scotland Yards

18-Acre Waterfront Sanctuary: Peace & Privacy

Find out more about Smith Island

Recent reviews of Smith Island properties

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

Waterfront Getaway: Kayaks, Paddle Board, Fishing!

Rodeway Inn at Somers Cove Marina

Pet-Friendly Smith Island Cottage w/ Golf Cart!

Historic home on Smith Island w/ dock!

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

𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻 𝐇𝐀𝐘𝐒 𝐁𝐄𝐀𝐂𝐇 step of your porch into the sand 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘

Get away to relax on Smith Island in the Chesapeake Bay with golf cart included

Bay Front Small Contemporary

Frequently asked questions