Smith Island Vacation Rentals

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Check prices for these dates

Tonight
Dec 31 - Jan 1
Tomorrow
Jan 1 - Jan 2
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Smith Island vacation rentals

Smart TV, fireplace, table tennis, books
Come escape to Smith Island for the winter and enjoy nature, peace and quiet

Vacation 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)
"Such a lovely, cozy little house. Right in town. We could walk to restaurants and the bakery. We really enjoyed talking with the islanders and the walk out to Rhodes Point was beautiful. "
United States
Debra M.
The price is ￥28,148
￥45,253 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Come escape to Smith Island for the winter and enjoy nature, peace and quiet
Fridge, microwave, oven, stovetop
Deal Island Bay Cottage

Cottage in Deal Island

Deal Island Bay Cottage
9.6 out of 10, Exceptional, (58)
"We got every year and stay here, it’s great! "
United States
Margaret H.
The price is ￥22,319
￥40,688 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Deal Island Bay Cottage
Smart TV, books
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Cottage in Point Lookout

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
9.4 out of 10, Exceptional, (9)
"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 ￥20,126
￥49,342 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Exterior
Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville

Vacation 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)
"Nice place "
United States
Luis A.
The price is ￥11,698
￥28,451 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville
Beach
Tangier Escape, great place get away from it all on Deal Island, MD.

Vacation 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)
"Helpful host, clean house, peaceful location! "
United States
Jennifer P.
The price is ￥14,856
￥31,826 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Tangier Escape, great place get away from it all on Deal Island, MD.
Dining
Cottage near the Bay

Vacation Home in Crisfield

Cottage near the Bay
8.8 out of 10, Excellent, (52)
"Great little place "
United States
Eric R.
The price is ￥12,634
￥29,098 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Cottage near the Bay
Smart TV
Newly updated 3 bedroom cottage with Solo Stove fire pit

Vacation Home in Reedville

Newly updated 3 bedroom cottage with Solo Stove fire pit
9.8 out of 10, Exceptional, (18)
"Great place "
United States
Myranda R.
The price is ￥13,757
￥37,354 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Newly updated 3 bedroom cottage with Solo Stove fire pit
Exterior detail
Reelin&Relaxin Spacious Farmhouse Reedville, VA Sleeps 8: 3 Bdrm 2 full bathroom

Vacation Home in Reedville

Reelin&Relaxin Spacious Farmhouse Reedville, VA Sleeps 8: 3 Bdrm 2 full bathroom
10.0 out of 10, Exceptional, (26)
"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 ￥25,735
￥60,415 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Reelin&Relaxin Spacious Farmhouse Reedville, VA Sleeps 8: 3 Bdrm 2 full bathroom
Outdoor dining
Bayfront Oasis with Heated Pool, Hot Tub & Playground! Family & Pet friendly!

Vacation Home in Reedville

Bayfront Oasis with Heated Pool, Hot Tub & Playground! Family & Pet friendly!
8.0 out of 10, Very Good, (1)
"We had a great time. The host was very welcoming and helpful. Hope to go back again."
United States
holly u.
The price is ￥87,041
￥180,985 total
includes taxes & fees
Jan 7 - Jan 8, 2026
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

Home of the Terrapin King

Home of the Terrapin King

10/10 Excellent
"It was an awesome weekend. My whole family made many memories and we can’t wait to come again! "
Nicol P. 2-night trip
Posted 3 weeks ago
Home of the Terrapin King

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 vacation rentals in Smith Island?

Yes, you can find vacation rentals close to the most popular attractions in Smith Island, or you can go with a secluded option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals in Smith Island?

Come escape to Smith Island for the winter and enjoy nature, peace and quiet : This highly rated vacation home rental in Smith Island offers a fireplace, a patio, and a barbecue grill 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 vacation with a garden and a selection of games. Our travelers also rate Spacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island as a favorite home for rent in Smith Island.

How many vacation rentals are there in Smith Island?

With 7 Expedia vacation rentals, you're sure 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 vacation rentals like in Smith Island?

Vacation rentals are privately owned properties you can reserve for a short or long stay in Smith Island. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll feel right at home. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for small groups.