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Smith Island Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Smith Island vacation rentals

A wooden deck with white railings, a door with a wreath, and two wicker chairs.

1. Come out and enjoy Autumn at the HH Ranch on Smith Island.

Come out and enjoy Autumn at the HH Ranch on Smith Island.
Smith Island
9.8 out of 10, Exceptional, (17 reviews)
"Visiting with locals, fresh steamed crabs, simply enjoying the quiet island life"
United States
Samantha J.
The price is ￥31,498
￥47,995 total
includes taxes & fees
Nov 9 - Nov 10
Come out and enjoy Autumn at the HH Ranch on Smith Island.
A room with a wooden bench, a lamp, a wicker basket, and a window with sheer curtains.

2. Cottage near the Bay

Cottage near the Bay
Crisfield
8.6 out of 10, Excellent, (65 reviews)
"Nice cottage at the end of a quiet lane, priced reasonably. Host is very accommodating. We had a lovely stay and enjoyed our time in Crisfield."
United States
Karen J.
The price is ￥12,757
￥28,046 total
includes taxes & fees
Nov 8 - Nov 9
Cottage near the Bay
A bedroom with a bed, bedside tables, a lamp, and a painting on the wall.

3. 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, (29 reviews)
"I always stay here when I come for work it’s a pretty nice place quiet and clean I highly recommend it to everyone it’s visiting"
United States
Luis A.
The price is ￥13,387
￥38,193 total
includes taxes & fees
Nov 29 - Nov 30
Newly updated 3 bedroom cottage with Solo Stove fire pit
A hallway with a framed artwork of a bird, a wooden entertainment unit with a TV, and a dining area with a bar stool.

4. Tangier Escape, great place get away from it all on Deal Island, MD.

Tangier Escape, great place get away from it all on Deal Island, MD.
Deal Island Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Helpful host, clean house, peaceful location! "
United States
Jennifer P.
The price is ￥20,474
￥40,567 total
includes taxes & fees
Nov 7 - Nov 8
Tangier Escape, great place get away from it all on Deal Island, MD.
A porch with two Adirondack chairs, a wooden table, and a view of a grassy yard and a house in the background.

5. 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, (31 reviews)
"The property was clean and comfortable. The deer playing in the field across the road was a nice sight sipping morning coffee."
United States
Charles
The price is ￥23,753
￥55,901 total
includes taxes & fees
Nov 15 - Nov 16
Reelin&Relaxin Spacious Farmhouse Reedville, VA Sleeps 8: 3 Bdrm 2 full bathroom
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a large island with stools.

6. Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (62 reviews)
"We got every year and stay here, it’s great! "
United States
Margaret H.
The price is ￥22,090
￥38,858 total
includes taxes & fees
Nov 8 - Nov 9
Deal Island Bay Cottage
A spacious room with a high ceiling, large windows, a ceiling fan, a dining area with a table and chairs, and a sofa.

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

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Point Lookout
9.0 out of 10, Wonderful, (22 reviews)
"Was very cozy and comfortable."
United States
sandi c.
The price is ￥34,963
￥65,168 total
includes taxes & fees
Dec 1 - Dec 2
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
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

Come out and enjoy Autumn at the HH Ranch on Smith Island.

Come out and enjoy Autumn at the HH Ranch on Smith Island.

10/10 Excellent
"Chris was very responsive and the house was lovely."
maureen g. 2-night trip
Posted 3 weeks ago
Come out and enjoy Autumn at the HH Ranch on Smith Island.

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?

Historic home on Smith Island w/ dock!: Visitors like this Smith Island vacation home rental. It is located on the waterfront and has a patio, a private yard, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of books.

How many vacation rentals are there in Smith Island?

With 8 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.