Smith Island Holiday Rentals

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Check prices for these dates

Tonight
3 Dec - 4 Dec
Tomorrow
4 Dec - 5 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Holiday Rentals in Smith Island

Smart TV, fireplace, ping pong, books
Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart

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 HK$1,549
HK$2,442 total
includes taxes & fees
5 Dec - 6 Dec
Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart
Beach
Historic home on Smith Island w/ dock!

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

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

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 HK$778
HK$1,629 total
includes taxes & fees
1 Jan - 2 Jan 2026
Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville
Outdoor dining
Near Chincoteague & Assateague Island Charming 2-bedroom cottage

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
On the beach, sun-loungers, beach towels
Private Beach Front Getaway at The Sunshine Beach Cottage.

Private Beach Front Getaway at The Sunshine Beach Cottage.

Point Lookout
9.8 out of 10, Exceptional, (80)
"We had a very nice and relaxing time on the beach and even got to watch a launch from wallops. "
United States
Ethan B.
Private Beach Front Getaway at The Sunshine Beach Cottage.
Property grounds
"Dragonfly" Waterfront Cottage on Chesapeake Bay

"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
Fridge, microwave, oven, stovetop
Call to reserve last minute stay! Hideaway in Hays Beach: 1 Minute Walk to Sand

Call to reserve last minute stay! Hideaway in Hays Beach: 1 Minute 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.
Call to reserve last minute stay! Hideaway in Hays Beach: 1 Minute Walk to Sand
Fridge, microwave, oven, stovetop
Private 5-acre Waterfront Retreat with Main & Guest House & BBQ Shed

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

Reedville
10.0 out of 10, Exceptional, (12)
"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
Property grounds
Bay Estate | Luxe Waterfront Home w/ Private Pier, Main+Guest House, Bay Views

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

Dameron
10.0 out of 10, Exceptional, (5)
"Such a beautiful house, very nice for family or friends get together."
United States
Yu S.
Bay Estate | Luxe Waterfront Home w/ Private Pier, Main+Guest House, Bay Views
On the beach, sun-loungers
Bay Front Small Contemporary

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

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

Reedville
9.6 out of 10, Exceptional, (95)
"Stay was great, host was very responsive! Cabbing was great fishing we weren’t as lucky but we would be back! "
United States
ReBecca S.
Private infinity pool, plus your own dock, kayaks, and bikes on the waterfront!
Interior
Spacious waterfront family retreat. Dogs welcome!, 1-Level Home w/ Rec Room and Fenced Yard

Spacious waterfront family retreat. Dogs welcome!, 1-Level Home w/ Rec Room and Fenced Yard

Northumberland County
10.0 out of 10, Exceptional, (8)
"Our stay at Paws and Reflect was wonderful. We and our friends enjoyed the location and the activities very much.The kitchen was very well stocked and the game room with music delightful. Your directions and information to kayak to the river were spot on. "
United States
Brad C G.
Spacious waterfront family retreat. Dogs welcome!, 1-Level Home w/ Rec Room and Fenced Yard
Outdoor dining
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10

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

Heathsville
9.6 out of 10, Exceptional, (43)
"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
Property grounds
𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻 𝐇𝐀𝐘𝐒 𝐁𝐄𝐀𝐂𝐇 step of your porch into the sand 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘

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

Point Lookout
10.0 out of 10, Exceptional, (124)
"Perfect place for a quiet getaway at the beach!"
United States
Cheryl S.
𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻 𝐇𝐀𝐘𝐒 𝐁𝐄𝐀𝐂𝐇 step of your porch into the sand 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘
Dining
Cottage near the Bay

Cottage near the Bay

Crisfield
8.8 out of 10, Excellent, (52)
"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 HK$631
HK$1,469 total
includes taxes & fees
8 Dec - 9 Dec
Cottage near the Bay
Games room
Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!

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

Reedville
9.8 out of 10, Exceptional, (63)
"What a wonderful stay!!"
United States
Anonymous traveller
Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!
Fridge, microwave, oven, stovetop
Deal Island Bay Cottage

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 HK$1,114
HK$2,047 total
includes taxes & fees
8 Dec - 9 Dec
Deal Island Bay Cottage
Property grounds
Beautiful Bayfront with Sanctuary Private Beach

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
Property grounds
Private, Waterfront, Ultra-clean, Pet friendly, Kayaks, Canoe, Firepit, more!

Private, Waterfront, Ultra-clean, Pet friendly, Kayaks, Canoe, Firepit, more!

Reedville
10.0 out of 10, Exceptional, (223)
"Host was very helpful and house was extremely clean!Restful few days!!!"
United States
Bjorndal S.
Private, Waterfront, Ultra-clean, Pet friendly, Kayaks, Canoe, Firepit, more!
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

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

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

10/10 Excellent
"The house and property were amazing. Our family felt right at home. Will definitely rent again!"
David M. 2-night trip
Posted 2 weeks ago
Private 5-acre Waterfront Retreat with Main & Guest House & BBQ Shed

Find out more about Smith Island

Search for holiday rentals in Smith Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Smith Island using one of the methods below:

  • View our selection of featured holiday rentals in Smith Island
  • Use the map to find apartments and other holiday homes in the Smith Island neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Smith Island while they last

Look no further and take a look at our great range of rental properties in Smith Island!

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. Horse Hammock and Tylerton County Dock 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.