Smith Island Holiday Rentals

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Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

Our top choices for Smith Island holiday rentals

Smart TV, fireplace, ping pong, books

Holiday Home in Smith Island

Come escape to Smith Island for the winter and enjoy nature, peace and quiet
9.8 out of 10, Exceptional, (15 reviews)
"This was our first visit to Smith Island and the Double H was perfect. It was close to the ferry landing so getting there was very easy. The house was well appointed and felt like home as soon as we arrived. We enjoyed the quiet of the island and we were able to fully disconnect and relax Thank you for a great day."
United States
Amanda W.
The price is HK$1,403
HK$2,265 total
includes taxes & fees
4 Feb - 5 Feb
Come escape to Smith Island for the winter and enjoy nature, peace and quiet
Exterior

Holiday Home in Reedville

Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville
2.0 star property
7.8 out of 10, Good, (8 reviews)
"Nice place "
United States
Luis A.
The price is HK$526
HK$1,360 total
includes taxes & fees
23 Jan - 24 Jan
Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville
3 bedrooms, free WiFi, bed sheets

Holiday Home in Reedville

Newly updated 3 bedroom cottage with Solo Stove fire pit
9.8 out of 10, Exceptional, (18 reviews)
"Great place "
United States
Myranda R.
The price is HK$688
HK$1,859 total
includes taxes & fees
26 Jan - 27 Jan
Newly updated 3 bedroom cottage with Solo Stove fire pit
Fridge, microwave, oven, stovetop

Cottage in Deal Island

Deal Island Bay Cottage
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$1,116
HK$2,043 total
includes taxes & fees
23 Jan - 24 Jan
Deal Island Bay Cottage
Dining

Cottage in Point Lookout

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
9.4 out of 10, Exceptional, (10 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$1,003
HK$2,460 total
includes taxes & fees
25 Jan - 26 Jan
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Beach

Holiday Home in Deal Island Historic District

Tangier Escape, great place get away from it all on Deal Island, MD.
10.0 out of 10, Exceptional, (1 review)
"Helpful host, clean house, peaceful location! "
United States
Jennifer P.
The price is HK$858
HK$1,926 total
includes taxes & fees
29 Jan - 30 Jan
Tangier Escape, great place get away from it all on Deal Island, MD.
Interior

Holiday Home in Crisfield

Cottage near the Bay
8.8 out of 10, Excellent, (52 reviews)
"Great little place "
United States
Eric R.
The price is HK$632
HK$1,463 total
includes taxes & fees
23 Jan - 24 Jan
Cottage near the Bay
Exterior detail

Holiday Home in Reedville

Reelin&Relaxin Spacious Farmhouse Reedville, VA Sleeps 8: 3 Bdrm 2 full bathroom
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$1,235
HK$2,957 total
includes taxes & fees
26 Jan - 27 Jan
Reelin&Relaxin Spacious Farmhouse Reedville, VA Sleeps 8: 3 Bdrm 2 full bathroom
Terrace/patio

Holiday Home in Reedville

Bayfront Oasis with Heated Pool, Hot Tub & Playground! Family & Pet friendly!
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$3,834
HK$8,414 total
includes taxes & fees
27 Jan - 28 Jan
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

Rodeway Inn at Somers Cove Marina

Rodeway Inn at Somers Cove Marina

10/10 Excellent
"Wonderful hotel staff Very clean room for a very good rate"
Alex 1-night trip
Posted 13 days ago
Rodeway Inn at Somers Cove Marina

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?

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 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.