Smith Island Holiday Rentals

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Our top choices for Smith Island holiday rentals

9.8 out of 10, Exceptional, (15)
"Such a lovely, cozy little house. Right in town. We could walk to restaurants and the bakery. We really enjoyed talking with the islanders and the walk out to Rhodes Point was beautiful. "
United States
Debra M.
The price is AU$430
includes taxes & fees
30 Jan - 31 Jan 2026
Come escape to Smith Island for the winter and enjoy nature, peace and quiet

Cottage in Deal Island

Deal Island Bay Cottage
9.6 out of 10, Exceptional, (58)
"We got every year and stay here, it’s great! "
United States
Margaret H.
The price is AU$395
includes taxes & fees
3 Jan - 4 Jan 2026
Deal Island Bay Cottage
9.4 out of 10, Exceptional, (9)
"The cottage was clean and welcoming. The location can't be beat. It is right on the water, quiet and nearby point lookout. Great place to visit and walk our dogs. The property owners were responsive and gave us a nice list of things to do around the area. Would definitely stay again!"
United States
Adam P.
The price is AU$476
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
7.8 out of 10, Good, (8)
"Nice place "
United States
Luis A.
The price is AU$275
includes taxes & fees
25 Jan - 26 Jan 2026
Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville
10.0 out of 10, Exceptional, (1)
"Helpful host, clean house, peaceful location! "
United States
Jennifer P.
The price is AU$307
includes taxes & fees
7 Jan - 8 Jan 2026
Tangier Escape, great place get away from it all on Deal Island, MD.

Holiday Home in Crisfield

Cottage near the Bay
8.8 out of 10, Excellent, (52)
"Great little place "
United States
Eric R.
The price is AU$283
includes taxes & fees
4 Jan - 5 Jan 2026
Cottage near the Bay
9.8 out of 10, Exceptional, (18)
"Great place "
United States
Myranda R.
The price is AU$361
includes taxes & fees
1 Jan - 2 Jan 2026
Newly updated 3 bedroom cottage with Solo Stove fire pit
10.0 out of 10, Exceptional, (26)
"We stayed while visiting for a family member graduation. The property was wonderful; the kitchen was well supplied and the little ones loved the games! Everything was very clean and comfortable. The owner was very responsive with any questions I had. We plan on staying here again the next time we are in town!"
United States
Sarah B.
The price is AU$583
includes taxes & fees
28 Jan - 29 Jan 2026
Reelin&Relaxin Spacious Farmhouse Reedville, VA Sleeps 8: 3 Bdrm 2 full bathroom
8.0 out of 10, Very good, (1)
"We had a great time. The host was very welcoming and helpful. Hope to go back again."
United States
holly u.
The price is AU$1,722
includes taxes & fees
7 Jan - 8 Jan 2026
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

Find out more about Smith Island

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, 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 favourite 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 depend 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 AU$283 per night. Entering your travel dates in the search wizard might find you 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?

Come escape to Smith Island for the winter and enjoy nature, peace and quiet : This highly rated holiday home rental in Smith Island offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You can relax into your holiday with a garden and a selection of games. Our travellers also rate Spacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island as a favourite home for rent in Smith Island.

How many holiday rentals are there in Smith Island?

With 7 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?

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 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.