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Holiday Homes in Smith Island

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Smith Island holiday homes

A marina at sunset with boats docked and buildings in the background.

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 €300
includes taxes & fees
21 Nov - 22 Nov
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, (64 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 €170
includes taxes & fees
3 Nov - 4 Nov
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, (28 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 €226
includes taxes & fees
22 Oct - 23 Oct
Newly updated 3 bedroom cottage with Solo Stove fire pit
A sandy beach with footprints, a pier in the distance, and a clear sky.

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 €225
includes taxes & fees
28 Oct - 29 Oct
Tangier Escape, great place get away from it all on Deal Island, MD.
A white door with a glass panel and a sunflower decoration, flanked by two wall-mounted lanterns.

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, (29 reviews)
"The host was amazing and the house was just as amazing."
United States
Mark R.
The price is €320
includes taxes & fees
22 Oct - 23 Oct
Reelin&Relaxin Spacious Farmhouse Reedville, VA Sleeps 8: 3 Bdrm 2 full bathroom
A covered outdoor deck with a view of a lake, wooden furniture, and a ceiling fan.

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

Bayfront Oasis with Heated Pool, Hot Tub & Playground! Family & Pet friendly!
Reedville
9.0 out of 10, Wonderful, (2 reviews)
"We had a great time. The host was very welcoming and helpful. Hope to go back again."
United States
holly u.
The price is €1,079
includes taxes & fees
22 Oct - 23 Oct
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

Find out more about Smith Island

Smith Island Holiday Homes information

Number of reviews
142
Accommodation
90 Holiday Homes
Lowest Price
€170
Highest Price
€1,079