Smith Island Holiday Rentals

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Holiday Rentals in Smith Island

Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart

Smith Island
9.8 out of 10, Exceptional, (15)
"The perfect place to wind down, reconnect with people, culture and a way of life we’ve strayed away from. The house was amazing! The town, the good people and the atmosphere just as much. "
United States
David
The price is NZ$554
includes taxes & fees
21 Nov - 22 Nov
Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart

Historic home on Smith Island w/ dock!

Smith Island
9.6 out of 10, Exceptional, (46)
"Very nice property! Spacious rooms, great host"
United States
Sara L.
Historic home on Smith Island w/ dock!

Spacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island

Smith Island
10.0 out of 10, Exceptional, (1)
"Amazing adventure! Peaceful! Beautiful! Privacy! Gourmet Kitchen! The house is set back from the neighborhood on a large lot. The decks are new and comfortably furnished. We cooked breakfast and dinner for 3 days and the well-equipped kitchen was perfect. Our days started and ended with gourmet meals, on the deck, emersed in the salt marsh. We explored the creeks, guts, and islands all around Ewell, Rhodes Point and Tylerton. Rich and Dani helped coordinate a private charter boat to bring our...
United States
Brent E.
Spacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island

Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!

Reedville
9.8 out of 10, Exceptional, (62)
"Beautiful house with great views, fantastic amenities. "
United States
Monica
Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!

Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville

2.0 star property
Reedville
8.0 out of 10, Very good, (7)
"Nice place "
United States
Luis A.
The price is NZ$356
includes taxes & fees
21 Nov - 22 Nov
Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville

Near Chincoteague & Assateague Island Charming 2-bedroom cottage

Saxis
9.4 out of 10, Exceptional, (3)
"Lovely, small but cozy, great place to bond and enjoy good food and drink."
United States
Bob H.
Near Chincoteague & Assateague Island Charming 2-bedroom cottage

"Dragonfly" Waterfront Cottage on Chesapeake Bay

2.5 star property
Reedville
10.0 out of 10, Exceptional, (3)
"Great getaway location right on th4e water. Highly recommended"
United States
James P.
"Dragonfly" Waterfront Cottage on Chesapeake Bay

A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 1 Min Walk to Sand

Point Lookout
10.0 out of 10, Exceptional, (125)
"Really enjoyed our time here. The outdoor space in the back was great with the swing and the fire pits. Our kids loved walking to the beach everyday and catching crabs. "
United States
David Z.
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 1 Min Walk to Sand

Private 5-acre Waterfront Retreat with Main & Guest House & BBQ Shed

Reedville
10.0 out of 10, Exceptional, (11)
"We enjoyed our family vacation, so relaxing and accommodating. Loved the location and setup. "
United States
Tina h.
Private 5-acre Waterfront Retreat with Main & Guest House & BBQ Shed

Bay Estate | Luxe Waterfront Home w/ Private Pier, Main+Guest House, Bay Views

Dameron
10.0 out of 10, Exceptional, (4)
"The home is stunning, exactly as advertised. There was plenty of room for myself, husband, grown children, and their children. The view is amazing!"
United States
Dianne P.
Bay Estate | Luxe Waterfront Home w/ Private Pier, Main+Guest House, Bay Views

Bay Front Small Contemporary

Reedville
9.8 out of 10, Exceptional, (115)
"Great place with a spectacular view. Would definitely love to stay again!"
United States
Jasper W.
Bay Front Small Contemporary

River front Home built in 2021 with Private Pier

Reedville
10.0 out of 10, Exceptional, (11)
"Great stay"
United States
Peyton S.
River front Home built in 2021 with Private Pier

Private infinity pool, plus your own dock, kayaks, and bikes on the waterfront!

Reedville
9.6 out of 10, Exceptional, (95)
"Great place to relax and catch blue crabs!we enjoy kayaking, pool coziness of the place. Only one thing we wish was little bit better was Wi-Fi connection but otherwise everything was perfection.!!!"
United States
Maria A.
Private infinity pool, plus your own dock, kayaks, and bikes on the waterfront!

Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks

Point Lookout
10.0 out of 10, Exceptional, (76)
"Our second stay at this wonderful property!"
United States
Beth C.
Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks

Private Beach Front Getaway at The Sunshine Beach Cottage.

Point Lookout
9.8 out of 10, Exceptional, (80)
"A charming and cozy cottage right on the water - caught and ate crabs every day and loved kayaking down the creek through the serene marshland!"
United States
Melissa D.
Private Beach Front Getaway at The Sunshine Beach Cottage.

Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10

Heathsville
9.6 out of 10, Exceptional, (42)
"This property was beautiful and was everything we were looking for in a last minute getaway on the water."
United States
Stacy R.
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10

𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻 𝐇𝐀𝐘𝐒 𝐁𝐄𝐀𝐂𝐇 step of your porch into the sand 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘

Point Lookout
10.0 out of 10, Exceptional, (124)
"This was the perfect spot for our first vacation with our baby. Quiet, private, and fun! So glad we stayed. "
United States
Paige T.
𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻 𝐇𝐀𝐘𝐒 𝐁𝐄𝐀𝐂𝐇 step of your porch into the sand 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘

Cottage near the Bay

Crisfield
8.8 out of 10, Excellent, (51)
"We had a great time! Everything went smoothly from beginning to end! We would definitely stay here again. "
United States
Jennifer J.
The price is NZ$333
includes taxes & fees
21 Nov - 22 Nov
Cottage near the Bay

Deal Island Bay Cottage

Deal Island
9.6 out of 10, Exceptional, (57)
"We got every year and stay here, it’s great! "
United States
Margaret H.
The price is NZ$465
includes taxes & fees
24 Nov - 25 Nov
Deal Island Bay Cottage

Beautiful Bayfront with Sanctuary Private Beach

Saxis
9.2 out of 10, Wonderful, (24)
"It was very easy to check-in to the home. The kitchen is well-equipped & all was very clean. It's a very nice home. We enjoyed it there. Nice & quiet. "
United States
CHERYL F.
Beautiful Bayfront with Sanctuary Private Beach
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 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 NZ$333 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?

Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart: 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.