Smith Island Vacation Rentals

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Vacation Rentals in Smith Island

IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
Exterior
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
10.0 out of 10, Exceptional, (11)
"The property was amazing and any minor issue we had. They were right there to fix it. The island was welcoming, as well as just the right amount of quiet and slow down that we were looking for. I recommend anybody needing to detach disconnect to enjoy property for a couple of days or even longer. The hospitality was amazing. We will be back."
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
Waterfront Reedville Home w/ Private Dock!
Fridge, microwave, stovetop, dishwasher
Waterfront Reedville Home w/ Private Dock!
10.0 out of 10, Exceptional, (7)
"The property was way better than we expected. We will definitely come back."
Waterfront Reedville Home w/ Private Dock!
Simply the best...Beautiful condo overlooking the Chesapeake bay.
Smart TV, fireplace
Simply the best...Beautiful condo overlooking the Chesapeake bay.
10.0 out of 10, Exceptional, (100)
"Beautifully decorated and having an awesome view, this condo brings pure Joy!"
Simply the best...Beautiful condo overlooking the Chesapeake bay.
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**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
Fridge, microwave, oven, stovetop
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
10.0 out of 10, Exceptional, (170)
"We spent the weekend relaxing in the outdoors with family. We kayaked, had an outdoor fire and enjoyed the wildlife that floated or flew by."
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
Waterfront Scotland Beach Retreat w/Private Beach!
On the beach
Waterfront Scotland Beach Retreat w/Private Beach!
10.0 out of 10, Exceptional, (34)
"We enjoyed our stay at this beautiful home. The property is very clean and the owner's have spent a great deal of attention to detail and design. The location is quiet and the views of the bay are spectacular. Our final night included a beautiful starry sky filled with views of the milky way and shooting stars."
Waterfront Scotland Beach Retreat w/Private Beach!
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10
Property grounds
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10
10.0 out of 10, Exceptional, (23)
"Situated on a point with water on two sides of the expansive property, the setting was amazing. The house is a mid-century ranch that has been thoroughly updated. We had lousy weather, so we did not get to enjoy the large water-side deck and firepit, but even the indoor views of the water from the kitchen-den area were wonderful."
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10
Waterfront House with Private Dock and Fishing
Smart TV
Waterfront House with Private Dock and Fishing
10.0 out of 10, Exceptional, (1)
"Our stay was wonderful...from the home accommodations to the outdoor environment. The crabbing was incredible. No doubt, we would stay again."
The price is $182
$522 total
includes taxes & fees
May 9 - May 10
Waterfront House with Private Dock and Fishing
No longer taking reservations at this time. Our apologies.
Fridge, microwave, oven, stovetop
No longer taking reservations at this time. Our apologies.
10.0 out of 10, Exceptional, (4)
"Great communication from host. Cleanliness of the property, quiet. Great views of the water. Would definitely book again"
No longer taking reservations at this time. Our apologies.
Secluded, Waterfront Home: Huge Game Room, Private Dock, Pedal Boat, & 4 Kayaks!
Game room
Secluded, Waterfront Home: Huge Game Room, Private Dock, Pedal Boat, & 4 Kayaks!
10.0 out of 10, Exceptional, (34)
"The home was exactly as described. Just pack a bag and everything else is there. Fully equipped property in a quiet location. The only thing I will add is the master bed was smaller than desired, otherwise everything was perfect! We would love to return at another time when the temps are warmer."
Secluded, Waterfront Home: Huge Game Room, Private Dock, Pedal Boat, & 4 Kayaks!
Private Beach Front Getaway at The Sunshine Beach Cottage.
On the beach, sun loungers, beach towels
Private Beach Front Getaway at The Sunshine Beach Cottage.
9.8 out of 10, Exceptional, (45)
"My husband and I have been to this cottage once before. It's our secret getaway. It has everything you need plus the beach is just a few feet away. You can't find another place like this one!"
Private Beach Front Getaway at The Sunshine Beach Cottage.
Bay Front Small Contemporary
Aerial view
Bay Front Small Contemporary
9.8 out of 10, Exceptional, (90)
"This property was so clean, the views out the windows were spectacular, and the water is right there! I greatly enjoyed the kayak and my dog just loved the privacy he had to play in the water. The host was extremely quick to respond and was one of the nicest hosts we've ever had. Highly recommend this spot and we can't wait to return!"
Bay Front Small Contemporary
BEACH COTTAGE BY THE SEA....
Property grounds
BEACH COTTAGE BY THE SEA....
9.8 out of 10, Exceptional, (17)
"We loved this quiet property, right on the water. The house was clean and perfect for my mom and me. I didn’t use the kitchen but it was stocked with a lot of stuff. Towels for the beach were provided, along with chairs for sitting on the beach. There is a rinse off area in the back of the house, but to turn the water on you have to go in front of the house. I absolutely would return. "
BEACH COTTAGE BY THE SEA....
Idyllic Waterfront Home w/ Game Room, Shared Dock
Property grounds
Idyllic Waterfront Home w/ Game Room, Shared Dock
9.8 out of 10, Exceptional, (14)
"Four sisters enjoyed a wonderful weekend that included walks, sitting on the dock, games, grilling, fire pit, a wine festival, and a farmers market. Great space with beautiful views. Do as much or as little as you want. We will be back."
Idyllic Waterfront Home w/ Game Room, Shared Dock
Million Dollar View, river house w/ private dock & beach area
Property grounds
Million Dollar View, river house w/ private dock & beach area
9.6 out of 10, Exceptional, (37)
"Great house, exceptionally clean with wonderful views! We couldn't have asked for a better place."
Million Dollar View, river house w/ private dock & beach area
'River's Edge Retreat’ with Kayaks & River Access!
TV, fireplace, video games, DVD player
'River's Edge Retreat’ with Kayaks & River Access!
9.6 out of 10, Exceptional, (52)
"We stayed 4 nights for a Spring Break with our family. The house was huge for the 5 of us. The kids had endless fun with the pool table, foosball table, darts, gaming, and movies. The kitchen is well equipped with everything you need to cook. There is definitely an ant issue in the kitchen even before we brought groceries in but we just kept everything sealed. The view is beautiful! Lots of books/magazines to read. No fires allowed in fireplaces unfortunately. Towels and linens provided were...
'River's Edge Retreat’ with Kayaks & River Access!
Inchgarth at Scotland Yards
On the beach
Inchgarth at Scotland Yards
9.6 out of 10, Exceptional, (103)
"Great house with beautiful location. Beach access is a little difficult, but we had enough people that we also rented the house next door, so all worked out. Lots of space in the house. All rooms are adequate size for families. We hope to return."
Inchgarth at Scotland Yards
Newly updated 3 bedroom cottage with Solo Stove fire pit
Smart TV
Newly updated 3 bedroom cottage with Solo Stove fire pit
9.6 out of 10, Exceptional, (4)
"We had a wonderful weekend on the Chesapeake Bay."
Newly updated 3 bedroom cottage with Solo Stove fire pit
Kentigern Shed at Scotland Yards
1 bedroom, WiFi, bed sheets
Kentigern Shed at Scotland Yards
9.6 out of 10, Exceptional, (147)
"We had a wonderful weekend. The views are amazing and more amazing views are close by at Point Lookout State Park."
Kentigern Shed at Scotland Yards
Historic home on Smith Island w/ dock!
Beach
Historic home on Smith Island w/ dock!
9.4 out of 10, Exceptional, (29)
"This was one of the most relaxing stays the family has ever had. Who can argue with Smith Island Cake from the bakery for breakfast!! The house was a great little hideaway to celebrate a 14th birthday and a 23rd anniversary. Having easy access to a boat dock allowed us to bring our own boat and so the freedom to fish the waters surrounding Smith Island, an afternoon trip to Tylerton for the absolute delicious crab cakes and a chat with Duke, a day trip to Crisfield for the annual boat docking...
Historic home on Smith Island w/ dock!
Rock Hall on the water
Lake
Rock Hall on the water
9.4 out of 10, Exceptional, (42)
"We were scouting this house as a potential place to bring friends, and while we really liked the house there are a few things we noticed that might make us hesitant to bring a larger group. The ground floor was badly in need of vacuuming and there was hair in the shower drain. We never could connect to internet and had no cell service so couldn't even let anyone know. Finally, the water has a highly sulfur odor. Overall it seemed no-one had been in the house in a while and it needed some more...
Rock Hall on the water
Don't see what you're looking for?
See all available properties in Smith Island
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.

Smith Island Vacation Rental Travel Info

Number of vacation rentals
3
Popular accommodation
Smith Island private vacation homes
Known landmarks
J. Millard Tawes Museum
International airport
Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)

Other types of properties in Smith Island you may be interested in

IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
Exterior
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
10.0 out of 10, Exceptional, (11)
"The property was amazing and any minor issue we had. They were right there to fix it. The island was welcoming, as well as just the right amount of quiet and slow down that we were looking for. I recommend anybody needing to detach disconnect to enjoy property for a couple of days or even longer. The hospitality was amazing. We will be back."
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
Waterfront Reedville Home w/ Private Dock!
Fridge, microwave, stovetop, dishwasher
Waterfront Reedville Home w/ Private Dock!
10.0 out of 10, Exceptional, (7)
"The property was way better than we expected. We will definitely come back."
Waterfront Reedville Home w/ Private Dock!
Private Beach Front Getaway at The Sunshine Beach Cottage.
On the beach, sun loungers, beach towels
Private Beach Front Getaway at The Sunshine Beach Cottage.
9.8 out of 10, Exceptional, (45)
"My husband and I have been to this cottage once before. It's our secret getaway. It has everything you need plus the beach is just a few feet away. You can't find another place like this one!"
Private Beach Front Getaway at The Sunshine Beach Cottage.
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.

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 $182 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?

Waterfront Reedville Home w/ Private Dock!: This vacation home near Smith Island is located on the waterfront and has a selection of games, a barbecue grill, and air-conditioning 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.

How many vacation rentals are there in Smith Island?

With 4 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?

Explore the area and family-friendly sights such as Reedville Fishermen's Museum, or get out into nature at a spot like Smith Island. In the larger area, you’ll find Tangier Island and Point Lookout State Park.

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.

Recent reviews of Smith Island properties
Expedia verified reviews

Simply the best...Beautiful condo overlooking the Chesapeake bay.

Simply the best...Beautiful condo overlooking the Chesapeake bay.

5/5 Excellent
A Peace of Heaven
"Beautifully decorated and having an awesome view, this condo brings pure Joy!"
A verified traveler stayed at Simply the best...Beautiful condo overlooking the Chesapeake bay.
Posted 7 days ago
Simply the best...Beautiful condo overlooking the Chesapeake bay.