Holiday Rentals in Smith Island

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Smith Island

Historic home on Smith Island w/ dock!
9.4 out of 10, Exceptional, (30)
"This was a perfect spot for out three-generation getaway. Property was a perfect fit for us and the new deck with screened-in porch is a great addition to this property. Well stocked kitchen made meal prep a breeze, and the gas grill came in very handy. Comfy furniture and a great dining room table perfect to game night."
Historic home on Smith Island w/ dock!
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
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
Save an average of 15% on thousands of hotels when you're signed in
Beautiful Bayfront with Sanctuary Private Beach
9.2 out of 10, Wonderful, (10)
"House was exactly as advertised and expected. Would stay agian for sure"
The price is €375
includes taxes & fees
9 Jun - 10 Jun
Beautiful Bayfront with Sanctuary Private Beach
Cottage near the Bay
9.0 out of 10, Wonderful, (13)
"Come stay at this wonderful house in lovely Crisfield Maryland. You won't be sorry. The host is fantastic and gets back to you quickly if you have questions. Thank you for everything."
The price is €187
includes taxes & fees
4 Jun - 5 Jun
Cottage near the Bay
Waterfront 3 bedroom condo. Spring is here!
10.0 out of 10, Exceptional, (20)
"Very relaxing time. The condo was beautiful"
Waterfront 3 bedroom condo. Spring is here!
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!
Private Beach Front Getaway at The Sunshine Beach Cottage.
9.8 out of 10, Exceptional, (46)
"Comfortable, clean home directly on the Chesapeake Bay."
Private Beach Front Getaway at The Sunshine Beach Cottage.
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!
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10
10.0 out of 10, Exceptional, (25)
"Beautiful! The home was very clean, and fully stocked with everything you'd need during your stay. Had a lot of fun visiting the nearby towns--definitely had the small-town atmosphere. The cell phone service presented a challenge though. The three of us whose carrier was Verizon had no problem at all, but the other party who had another carrier was unable to get a connection unless we went closer to town. Something to consider. Also, we were unable to get local channels/cable on the TV. Used...
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10
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
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"
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
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
10.0 out of 10, Exceptional, (171)
"Groomsmen stayed here for wedding. Great experience in a beautiful location. Swimming and kayaking right out the back door. Owners were very kind and helpful. Definitely recommend this beautiful spot."
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
Quaint Island Getaway
10.0 out of 10, Exceptional, (11)
"This is a charming place, full of really nice interior touches. The location gives you access to some great marshland so you are treated to a daily dose of great bird sightings, including ospreys, red-winged blackbirds, herons and others. The house has everything you need. The only advice I would give - to remind guests to clean off the grill when they are done using it. We had to clean it thoroughly as it had obviously not been cleaned in awhile. I suggest you add that to the short list of...
Quaint Island Getaway
Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger
9.8 out of 10, Exceptional, (10)
"Just as advertised!!!! Highly recommend!!"
Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger
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!
Charming cottage on Chesapeake Bay with private sand beach and 1 acre to play on
10.0 out of 10, Exceptional, (17)
"Everything at the property was as advertised. Just bring the fam and food and everything else is taken care of. Really enjoyed the added touches like providing a s'mores kit, or having cold drinks already available upon check in as provided by host. Don't let this one slip away and enjoy your stay at the kozy kottage"
Charming cottage on Chesapeake Bay with private sand beach and 1 acre to play on
Waterfront Heathsville Cottage w/ Dock & Hot Tub!
10.0 out of 10, Exceptional, (88)
"Stay was lovely."
Waterfront Heathsville Cottage w/ Dock & Hot Tub!
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

Historic home on Smith Island w/ dock!
9.4 out of 10, Exceptional, (30)
"This was a perfect spot for out three-generation getaway. Property was a perfect fit for us and the new deck with screened-in porch is a great addition to this property. Well stocked kitchen made meal prep a breeze, and the gas grill came in very handy. Comfy furniture and a great dining room table perfect to game night."
Historic home on Smith Island w/ dock!
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
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
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 €187 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?

Beautiful Bayfront with Sanctuary Private Beach : This holiday home rental outside of Smith Island has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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