Smith Island Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
27 Mar - 29 Mar
In two months
8 May - 10 May
In three months
5 Jun - 7 Jun
In four months
3 Jul - 5 Jul

Our top choices for Smith Island holiday rentals

Terrace/patio

Historic home on Smith Island w/ dock!

Historic home on Smith Island w/ dock!
Smith Island
9.6 out of 10, Exceptional, (46 reviews)
"Very nice property! Spacious rooms, great host"
United States
Sara L.
The price is HK$1,558
HK$2,415 total
includes taxes & fees
31 Mar - 1 Apr
Historic home on Smith Island w/ dock!
Marina

Come escape to Smith Island for the Spring and enjoy nature, peace and quiet

Come escape to Smith Island for the Spring and enjoy nature, peace and quiet
Smith Island
9.8 out of 10, Exceptional, (15 reviews)
"Excellent property, excellent host. This is a very well-appointed property located very close to the ferry dock. Golf cart, bikes, and kayaks were in great shape. Chris could not have been a more responsive or helpful host."
United States
Timothy S.
The price is HK$1,761
HK$2,800 total
includes taxes & fees
1 Apr - 2 Apr
Come escape to Smith Island for the Spring and enjoy nature, peace and quiet
Interior

Cottage near the Bay

Cottage near the Bay
Crisfield
8.8 out of 10, Excellent, (52 reviews)
"Great little place "
United States
Eric R.
The price is HK$634
HK$1,460 total
includes taxes & fees
16 Mar - 17 Mar
Cottage near the Bay
Exterior

Kentigern Shed at Scotland Yards

Kentigern Shed at Scotland Yards
Point Lookout
9.6 out of 10, Exceptional, (155 reviews)
"Nice place to stay and very enjoyable environment. Management team is excellent to handle the property. "
United States
william s.
The price is HK$1,346
HK$2,554 total
includes taxes & fees
16 Mar - 17 Mar
Kentigern Shed at Scotland Yards
Fridge, microwave, oven, stovetop

Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (58 reviews)
"We got every year and stay here, it’s great! "
United States
Margaret H.
The price is HK$1,092
HK$2,037 total
includes taxes & fees
16 Mar - 17 Mar
Deal Island Bay Cottage
3 bedrooms, free WiFi, bed sheets

Newly updated 3 bedroom cottage with Solo Stove fire pit

Newly updated 3 bedroom cottage with Solo Stove fire pit
Reedville
9.6 out of 10, Exceptional, (20 reviews)
"Great place "
United States
Myranda R.
The price is HK$740
HK$1,903 total
includes taxes & fees
22 Mar - 23 Mar
Newly updated 3 bedroom cottage with Solo Stove fire pit
Dining

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Point Lookout
9.4 out of 10, Exceptional, (12 reviews)
"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 HK$1,558
HK$3,164 total
includes taxes & fees
16 Mar - 17 Mar
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Exterior detail

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

Reelin&Relaxin Spacious Farmhouse Reedville, VA Sleeps 8: 3 Bdrm 2 full bathroom
Reedville
10.0 out of 10, Exceptional, (26 reviews)
"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 HK$1,174
HK$2,806 total
includes taxes & fees
16 Mar - 17 Mar
Reelin&Relaxin Spacious Farmhouse Reedville, VA Sleeps 8: 3 Bdrm 2 full bathroom
Terrace/patio

Bayfront Oasis with Heated Pool, Hot Tub & Playground! Family & Pet friendly!

Bayfront Oasis with Heated Pool, Hot Tub & Playground! Family & Pet friendly!
Reedville
8.0 out of 10, Very good, (1 review)
"We had a great time. The host was very welcoming and helpful. Hope to go back again."
United States
holly u.
The price is HK$5,606
HK$10,711 total
includes taxes & fees
22 Mar - 23 Mar
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Smith Island Hotel Reviews

FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS

FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS

10/10 Excellent
"Thank you for everything and the flexibility with check in/out times. We will be back in July"
Katie B. 3-night trip
Posted 7 days ago
FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS

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?

Spacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island: 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. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and an arcade/games room.

How many holiday rentals are there in Smith Island?

With 6 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.