Holiday Rentals in Smith Island

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Holiday Rentals in Smith Island

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
Property grounds
Blue Anchor Cottage at Smith Island MD Quaint & Charming Beach Cottage
10.0 out of 10, Exceptional, (1)
"As many reviewers say, Smith Island is not a hot spot teaming with places to go. We knew this when booking. We brought our cameras, our water colors to paint, books, knitting, cards.... we had a WONDERFUL time. The cottage was beautiful and had everything we needed. The host even supplied us with board games and bug spray. We walked the length of the island several times and spent most mornings with our binoculars and cameras birding. If you want to relax and can entertain yourself it is a...
Blue Anchor Cottage at Smith Island MD Quaint & Charming Beach Cottage
Fridge, microwave, stovetop, dishwasher
Waterfront Reedville Home w/ Private Dock!
10.0 out of 10, Exceptional, (8)
"Very accommodating, comfy beds (a real +). Kitchen fully loaded with supplies (including spices and condiments). We spent so much time down on the dock crabbing and fishing. Our dogs loved the freedom and space. Made friends with others in the area and did dog walks with them."
Waterfront Reedville Home w/ Private Dock!
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TV, fireplace, DVD player, table football
Virginia Retreat on Wicomico River w/ Dock!
10.0 out of 10, Exceptional, (6)
"Gorgeous location on the Great Wicomico!! Beautiful home with both a rustic feel and lovely modern additions. We brought our boat and the cove on Cole’s Creek was well protected with deep water. Property grounds were so nice, lots of space, and gorgeous view! The owner was super supportive and very helpful with recommendations in the area. Highly recommend!!"
Virginia Retreat on Wicomico River w/ Dock!
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
Property grounds
Panoramic Waterfront Retreat: Big 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."
Panoramic Waterfront Retreat: Big Game Room, Private Dock, Pedal Boat, 4 Kayaks!
Outdoor pool
Waterfront 3 bedroom condo. Spring is here!
10.0 out of 10, Exceptional, (18)
"Love the decor, furniture and everything you could want/need. Very comfortable and felt like a friend's house. Perfect for our girls trip and one day we never left the condo"
Waterfront 3 bedroom condo. Spring is here!
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**
Smart TV, fireplace
Simply the best...Beautiful condo overlooking the Chesapeake bay.
10.0 out of 10, Exceptional, (101)
"The condo was perfect. Checkin was easy, was as described and the view was amazing. Would recommend to anyone looking for a relaxing getaway"
Simply the best...Beautiful condo overlooking the Chesapeake bay.
Beach nearby, sun-loungers
Quaint Island Getaway
10.0 out of 10, Exceptional, (9)
"This was a very nice well kept home in historical Deal Island. This home was very well equipped with everything you need to make your stay comfortable. Which was really appreciated because there is no stores really close. I would definitely stay here again."
Quaint Island Getaway
Property grounds
Stylish Condo with a Great View
10.0 out of 10, Exceptional, (4)
"The property is in a great locationwith beautiful sunsets. It was perfect for a thanksgiving trip."
The price is €293
includes taxes & fees
23 May - 24 May
Stylish Condo with a Great View
Fridge, microwave, stovetop, dishwasher
Waterfront Heathsville Cottage w/ Dock & Hot Tub!
10.0 out of 10, Exceptional, (86)
"This had all the conveniences of home that are not normally found at a rental. We would definitely stay again."
Waterfront Heathsville Cottage w/ Dock & Hot Tub!
Combined shower/bathtub, hair dryer, towels, soap
Reelin&Relaxin Spacious Farmhouse Reedville, VA Sleeps 8 near Smith Point Marina
10.0 out of 10, Exceptional, (16)
"House was clean and as advertised. Check-in process was very easy."
The price is €386
includes taxes & fees
27 May - 28 May
Reelin&Relaxin Spacious Farmhouse Reedville, VA Sleeps 8 near Smith Point Marina
Terrace/patio
Come, sit back and relax at the "Catch of the Bay"
10.0 out of 10, Exceptional, (3)
"It was very good, very clean and cozy. I would recommend the place for sure."
Come, sit back and relax at the "Catch of the Bay"
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 €507
includes taxes & fees
23 May - 24 May
Waterfront House with Private Dock and Fishing
Interior
Hays Beach House - Hot Tub - Private Beach
10.0 out of 10, Exceptional, (1)
"This is our 16th year vacationing at Hay Beach, but our first time staying at this property. The house is very confrontable and the layout is great, plenty of room for our family, 3 couples. The second level deck was the hangout, beautiful views of the sun rises with morning coffee, watching large pods of dolphins swimming 30 yards off the beach, eagles flying overhead and cocktails every evening. The guys fished from kayaks while the girls laid in the sun on the deck every day ... great...
Hays Beach House - Hot Tub - Private Beach
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.
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
Smart TV, books
Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger
9.8 out of 10, Exceptional, (9)
"The cozy house make our weekend great! Nice view, we enjoyed kayak."
Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger
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....
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.

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

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
Property grounds
Blue Anchor Cottage at Smith Island MD Quaint & Charming Beach Cottage
10.0 out of 10, Exceptional, (1)
"As many reviewers say, Smith Island is not a hot spot teaming with places to go. We knew this when booking. We brought our cameras, our water colors to paint, books, knitting, cards.... we had a WONDERFUL time. The cottage was beautiful and had everything we needed. The host even supplied us with board games and bug spray. We walked the length of the island several times and spent most mornings with our binoculars and cameras birding. If you want to relax and can entertain yourself it is a...
Blue Anchor Cottage at Smith Island MD Quaint & Charming Beach Cottage
Fridge, microwave, stovetop, dishwasher
Waterfront Reedville Home w/ Private Dock!
10.0 out of 10, Exceptional, (8)
"Very accommodating, comfy beds (a real +). Kitchen fully loaded with supplies (including spices and condiments). We spent so much time down on the dock crabbing and fishing. Our dogs loved the freedom and space. Made friends with others in the area and did dog walks with them."
Waterfront Reedville Home w/ Private Dock!
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Smith Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Smith Island holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Smith Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Smith Island holiday rentals we have selected for you start as low as €188 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Smith Island rentals

At Expedia, we put the best Smith Island holiday 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 holiday.

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 holiday rentals in Smith Island?

Yes, there are holiday rentals close to the most popular sights in Smith Island, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Smith Island has to offer?

Waterfront Reedville Home w/ Private Dock!: This holiday home rental outside of Smith Island is located on the waterfront, and has a selection of games, a BBQ 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 that you can cook with friends or family.

How many holiday rentals are there in Smith Island?

With 4 Expedia holiday rentals, you're guaranteed 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 wider area, you’ll find Tangier Island and Point Lookout State Park.

What are holiday rentals like in Smith Island?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Smith Island. Holiday rentals provide amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for small groups.

Recent reviews of Smith Island properties
Expedia verified reviews

Waterfront Reedville Home w/ Private Dock!

Waterfront Reedville Home w/ Private Dock!

5/5 Excellent
A restful reprieve
"Very accommodating, comfy beds (a real +). Kitchen fully loaded with supplies (including spices and condiments). We spent so much time down on the dock crabbing and fishing. Our dogs loved the freedom and space. Made friends with others in the area and did dog walks with them."
A verified traveller from Fountain Hill, PA USA stayed at Waterfront Reedville Home w/ Private Dock!
Posted 6 days ago
Waterfront Reedville Home w/ Private Dock!