A person in a kayak on a calm body of water during sunset.

Smith Island Vacation Rentals

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Smith Island vacation rentals

Cottage (2 Bedrooms) | Interior

Pet-friendly Smith Island Cottage w/ Golf Cart!

Pet-friendly Smith Island Cottage w/ Golf Cart!
3.0 star property
Smith Island
10.0 out of 10, Exceptional, (1 review)
"We had a lovely 2 night stay. The owners and host were wonderful. We were so happy to have use of the golf cart and bicycles. The cottage is adorable with beautiful touches all around."
United States
Karl
Pet-friendly Smith Island Cottage w/ Golf Cart!
Marina

Summer is here on Smith Island! Come out and enjoy a great season on the Bay

Summer is here on Smith Island! Come out and enjoy a great season on the Bay
Smith Island
9.8 out of 10, Exceptional, (15 reviews)
"Visiting with locals, fresh steamed crabs, simply enjoying the quiet island life"
United States
Samantha J.
$326 nightly
The price is $360
Jul 10 - Jul 11
Total with taxes and fees
Summer is here on Smith Island! Come out and enjoy a great season on the Bay
Interior

Cottage near the Bay

Cottage near the Bay
Crisfield
8.8 out of 10, Excellent, (56 reviews)
"Cottage was exactly as listed. Great value"
United States
Tom B.
$176 nightly
The price is $187
Jul 19 - Jul 20
Total with taxes and fees
Cottage near the Bay
Beach

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

Tangier Escape, great place get away from it all on Deal Island, MD.
Deal Island Historic District
10.0 out of 10, Exceptional, (1 review)
"Helpful host, clean house, peaceful location! "
United States
Jennifer P.
$232 nightly
The price is $246
Jul 19 - Jul 20
Total with taxes and fees
Tangier Escape, great place get away from it all on Deal Island, MD.
Private kitchen

Saltwater Serenity Waterfront Cottage

Saltwater Serenity Waterfront Cottage
Deal Island Historic District
$355 nightly
The price is $377
Jul 14 - Jul 15
Total with taxes and fees
Saltwater Serenity Waterfront Cottage
Fridge, microwave, oven, stovetop

Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (59 reviews)
"We got every year and stay here, it’s great! "
United States
Margaret H.
$246 nightly
The price is $261
Jul 13 - Jul 14
Total with taxes and fees
Deal Island Bay Cottage
Free WiFi, bed sheets

Newly updated 3 bedroom cottage with Solo Stove fire pit

Newly updated 3 bedroom cottage with Solo Stove fire pit
Reedville
9.8 out of 10, Exceptional, (21 reviews)
"Great place "
United States
Myranda R.
$260 nightly
The price is $279
Jul 27 - Jul 28
Total with taxes and fees
Newly updated 3 bedroom cottage with Solo Stove fire pit
Exterior detail

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

Reelin&Relaxin Spacious Farmhouse Reedville, VA Sleeps 8: 3 Bdrm 2 full bathroom
Reedville
10.0 out of 10, Exceptional, (27 reviews)
"House was clean and as advertised. Check-in process was very easy."
United States
Anonymous traveler
$417 nightly
The price is $447
Aug 5 - Aug 6
Total with taxes and fees
Reelin&Relaxin Spacious Farmhouse Reedville, VA Sleeps 8: 3 Bdrm 2 full bathroom
Smart TV, fireplace, table tennis, books

Hideaway in Hays Beach: Western Sandy Shore of Chesapeake Bay and 5g WiFi!

Hideaway in Hays Beach: Western Sandy Shore of Chesapeake Bay and 5g WiFi!
Point Lookout
10.0 out of 10, Exceptional, (134 reviews)
"The property was very clean and well-stocked. Beds were comfortable and pictures matched reality. Jocelyn was so kind to leave us ingredients for smores and Easter eggs for my kids to have a hunt in the backyard. Overall, we had a wonderful stay and hope to make it back again some time!"
United States
Allie P.
$600 nightly
The price is $662
Jul 19 - Jul 20
Total with taxes and fees
Hideaway in Hays Beach: Western Sandy Shore of Chesapeake Bay and 5g WiFi!
Terrace/patio

Bayfront Oasis with Heated Pool, Hot Tub & Playground! Family & Pet friendly!

Bayfront Oasis with Heated Pool, Hot Tub & Playground! Family & Pet friendly!
Reedville
8.0 out of 10, Very Good, (1 review)
"We had a great time. The host was very welcoming and helpful. Hope to go back again."
United States
holly u.
Bayfront Oasis with Heated Pool, Hot Tub & Playground! Family & Pet friendly!
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.
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Top Smith Island Hotel Reviews

Rodeway Inn at Somers Cove Marina

Rodeway Inn at Somers Cove Marina

10/10 Excellent
"We just returned form an overnight stay, and we were so impressed! Super clean and spacious room, comfortable bed. We were there for the fireworks and couldn't ask for a better spot to view! The Patel family ( the owners) were so gracious and welcoming! They were hosting a family event and invited us to join. We are planning our trip back for next year! Highly recommend!"
Kathleen 1-night trip
Posted 2 days ago
Rodeway Inn at Somers Cove Marina

Find out more about Smith Island

Everything you need to know about Smith Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Smith Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Smith Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Smith Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Smith Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Smith Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $187 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Smith Island rentals

At Expedia, we put the best Smith Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Smith Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Smith Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Smith Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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!: This highly rated vacation home rental in Smith Island 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. Our travelers also rate Summer is here on Smith Island! Come out and enjoy a great season on the Bay as a favorite home for rent in Smith Island.

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 Chesapeake Bay are a couple of lovely local spots to get outside and enjoy nature. Tylerton County Dock and Horse Hammock are other places to visit while you're in town.

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.