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Smith Island Holiday Rentals

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Smith Island holiday rentals

Exterior

1. Pet-Friendly Smith Island Cottage w/ Golf Cart!

Pet-Friendly Smith Island Cottage w/ Golf Cart!
Ewell
10.0 out of 10, Exceptional, (23 reviews)
"The Castaway house was a wonderful spot for our family of 4. The house was so comfortable and it was fantastic to have access to the golf cart to tour the island!! The island was very welcoming. One highlight was a boat tour with Capt. Mark Kitching (410)603-1227. He took us through the marshes and outer islands, pointing out lots of birds (we saw Pelicans!!). Bring your own food if you want to cook- restaurants close early and groceries are limited. Cash or check for the boat over. It...
United States
Laura J.
Pet-Friendly Smith Island Cottage w/ Golf Cart!
Interior

2. Pet-friendly Smith Island Cottage w/ Golf Cart!

Pet-friendly Smith Island Cottage w/ Golf Cart!
3.0 star property
Smith Island
10.0 out of 10, Exceptional, (1 review)
"We had a lovely 2 night stay. The owners and host were wonderful. We were so happy to have use of the golf cart and bicycles. The cottage is adorable with beautiful touches all around."
United States
Karl
Pet-friendly Smith Island Cottage w/ Golf Cart!
Marina

3. 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, (16 reviews)
"Visiting with locals, fresh steamed crabs, simply enjoying the quiet island life"
United States
Samantha J.
The price is HK$1,765
HK$2,823 total
includes taxes & fees
20 Sept - 21 Sept
Come out and enjoy Autumn at the HH Ranch on Smith Island.
Interior

4. Cottage near the Bay

Cottage near the Bay
Crisfield
8.6 out of 10, Excellent, (62 reviews)
"Quiet area, the place needs to be cleaned, bedding changed, redo the bathroom"
United States
Pamela
The price is HK$635
HK$1,480 total
includes taxes & fees
27 Sept - 28 Sept
Cottage near the Bay
Beach

5. 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 HK$863
HK$1,929 total
includes taxes & fees
27 Sept - 28 Sept
Tangier Escape, great place get away from it all on Deal Island, MD.
Free WiFi, bed sheets

6. Newly updated 3 bedroom cottage with Solo Stove fire pit

Newly updated 3 bedroom cottage with Solo Stove fire pit
Reedville
9.4 out of 10, Exceptional, (26 reviews)
"Great place "
United States
Myranda R.
The price is HK$667
HK$1,936 total
includes taxes & fees
20 Sept - 21 Sept
Newly updated 3 bedroom cottage with Solo Stove fire pit
Coffee/tea maker, fridge, microwave, oven

7. Unique Tangier Cottage w/ Chesapeake Bay Views!

Unique Tangier Cottage w/ Chesapeake Bay Views!
Tangier
10.0 out of 10, Exceptional, (20 reviews)
"Ken & and family were wonderful hosts, his communication was perfect! The house was clean and a great place to stay. We had a wonderful weekend and can't wait to come back."
United States
Tim B.
Unique Tangier Cottage w/ Chesapeake Bay Views!
Coffee/tea maker, fridge, microwave, oven

8. Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (61 reviews)
"We were there for our granddaughter's wrestling tournament in Salisbury. House was excellent, quiet and clean. Beautiful home. Thank you."
United States
Christopher M.
The price is HK$1,123
HK$2,047 total
includes taxes & fees
20 Sept - 21 Sept
Deal Island Bay Cottage
Exterior detail

9. 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)
"House was clean and as advertised. Check-in process was very easy."
United States
Anonymous traveller
The price is HK$1,177
HK$2,896 total
includes taxes & fees
28 Sept - 29 Sept
Reelin&Relaxin Spacious Farmhouse Reedville, VA Sleeps 8: 3 Bdrm 2 full bathroom
Dining

10. 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, (18 reviews)
"Was very cozy and comfortable."
United States
sandi c.
The price is HK$1,742
HK$3,421 total
includes taxes & fees
19 Oct - 20 Oct
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Terrace/patio

11. 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.
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

Charming 2 Bedroom house in beautiful Smith Island Pet-Friendly Golf Cart

Charming 2 Bedroom house in beautiful Smith Island Pet-Friendly Golf Cart

10/10 Excellent
"This is a great place to stay on Smith Island. Easy access to most areas. The Golf cart is also nice to have. The house has everything you need and many extras too! Highly recommend a visit here."
Margaret A. 2-night trip
Posted 10 hours ago
Charming 2 Bedroom house in beautiful Smith Island Pet-Friendly Golf Cart

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?

Historic home on Smith Island w/ dock!: This highly rated holiday home rental in Smith Island is located on the waterfront, and has a patio, a private garden and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of books. Other favourite homes for rent in Smith Island are Charming 2 Bedroom house in beautiful Smith Island Pet-Friendly Golf Cart and Spacious 5-bedroom house with WiFi, AC and private deck on charming Smith Island.

How many holiday rentals are there in Smith Island?

With 8 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. Tylerton County Dock and Horse Hammock 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.