Holiday Rentals Smith Island from £144: Find Short-Term Rentals & Holiday Accommodations

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

Historic home on Smith Island w/ dock! : This highly rated holiday home rental in Smith Island is located on the waterfront, and has a patio, a private garden and a BBQ 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. You and your friends and family can relax into your holiday with amenities such as a selection of books. Our travellers also rate Spacious 5-bedroom house with WiFi, AC and private deck on charming Smith Island as a favourite home for rent in Smith Island.

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Our top choices for Smith Island holiday rentals

A marina at sunset with boats docked and buildings in the background.

1. Come out and enjoy Autumn at the HH Ranch on Smith Island.

Smith Island

Samantha J.

includes taxes & fees

16 Oct - 17 Oct

A room with a wooden bench, a lamp, a wicker basket, and a window with sheer curtains.

2. Cottage near the Bay

Crisfield

Pamela

includes taxes & fees

29 Sept - 30 Sept

A sandy beach with footprints, a pier in the distance, and a clear sky.

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

Deal Island Historic District

Jennifer P.

includes taxes & fees

5 Oct - 6 Oct

A bedroom with a bed, bedside tables, a lamp, and a painting on the wall.

4. Newly updated 3 bedroom cottage with Solo Stove fire pit

Reedville

Myranda R.

includes taxes & fees

29 Sept - 30 Sept

A modern kitchen with wooden ceiling, white cabinets, stainless steel appliances, and a central island with seating.

5. Unique Tangier Cottage w/ Chesapeake Bay Views!

Tangier

Tim B.

includes taxes & fees

5 Oct - 6 Oct

A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a large island with stools.

6. Deal Island Bay Cottage

Deal Island

"We loved this place! We were in town for baseball. It is very nice and has all the comforts of home. Kitchen big and well equipped, house was clean and very well furnished. Nice bathrooms and a lovely screened in back porch. It is very near a beautiful beach on the bay that has some of the most beautiful sunsets you will ever see. We really enjoyed this perk!! Prompt communication and everything was as described. I highly recommend this rental!!"

Harold B.

includes taxes & fees

1 Oct - 2 Oct

A white door with a glass panel and a sunflower decoration, flanked by two wall-mounted lanterns.

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

Reedville

Anonymous traveller

includes taxes & fees

29 Sept - 30 Sept

8. Unique Tangier Cottage w/ Chesapeake Bay Views!

Tangier

includes taxes & fees

5 Oct - 6 Oct

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Top Smith Island Hotel Reviews

Kingsbay Mansion & Vacation Houses

10/10 Excellent

"Great experience! The hosts were phenomenal, breakfast was really tasty as well, but the best & most memorable are the stories they willingly shared about their beautiful home, its history, and some of their of their personal experiences. Beautiful! Will be back to visit again."

Charming 2 Bedroom house in beautiful Smith Island Pet-Friendly Golf Cart

10/10 Excellent

"What a charming house! Great location and view of the water. Very clean, well-organized and stocked with everything that you could possibly need. We used the golf cart which is definitely the way to get around the island. Great experience and great owners."

𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻, ON THE SANDS OF THE 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘

10/10 Excellent

"This is the 2nd year I’ve rented this home on the Chesapeake, and I’ll definitely be back! Missy has thought of every comfort and convenience! The home is clean, spotless, bright and welcoming! The kitchen has all you’d ever need! The view is breathtaking; I was up every morning before sunrise to welcome the gorgeous day, and get out on the beach to see what the latest high tide brought in! The screened porch is my favorite viewing place, and this year Missy has added a deck in front of the screened porch which is wonderful! I really can’t recommend this perfect cottage too much!!!"

Beautiful Bayfront with Sanctuary Private Beach

10/10 Excellent

"This place is fantastic! Our family had a blast here. The beach was nice! Definitely bring the bug spray but for the most part it was just a few hours at dusk and mainly those greenhead flies on the beach. Wasn't a problem with a breeze off the water or a little fire in the fire pit. Read the reviews and we didn't have a problem with the fridge nice and cold and as for the well water.... If you haven't had it before I guess it could be a shock but after a day or 2 hardly noticeable and my kids didn't even notice. Lots of board games and seasonings and things if needed. The store is aways away but I'll take the peace and quiet and the stars over being close to a grocery store! The ac worked really well for the kid to have a cool down. Beautiful spot for sure with the water close, friendly waving neighbors, and lots of room for a variety of activities. The hosts were very quick to respond to questions and provided easy info for check in and check out. We will definitely be coming back!!"

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, 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 £144 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?

Historic home on Smith Island w/ dock!: This highly rated holiday home rental in Smith Island is located on the waterfront, and has a patio, a private garden and a BBQ 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. You and your friends and family can relax into your holiday with amenities such as a selection of books. Our travellers also rate Spacious 5-bedroom house with WiFi, AC and private deck on charming Smith Island as a favourite home for rent in Smith Island.

How many holiday rentals are there in Smith Island?

With 8 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.

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Our top choices for Smith Island holiday rentals