Smith Island Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Nov 15 - Nov 16
Tomorrow
Nov 16 - Nov 17
Next weekend
Nov 21 - Nov 23
In two weeks
Nov 28 - Nov 30

Vacation Rentals in Smith Island

Smart TV, fireplace, table tennis, books
Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart

Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart

Smith Island
9.8 out of 10, Exceptional, (15)
"The perfect place to wind down, reconnect with people, culture and a way of life we’ve strayed away from. The house was amazing! The town, the good people and the atmosphere just as much. "
United States
David
The price is ￥30,755
￥48,491 total
includes taxes & fees
Nov 20 - Nov 21
Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart
Fridge, microwave, oven, stovetop
Deal Island Bay Cottage

Deal Island Bay Cottage

Deal Island
9.6 out of 10, Exceptional, (57)
"Very nice house and close enough to go places but far enough to be peaceful."
United States
Larry F.
The price is ￥22,116
￥40,645 total
includes taxes & fees
Nov 17 - Nov 18
Deal Island Bay Cottage
Exterior
Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville

Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville

2.0 star property
Reedville
8.0 out of 10, Very Good, (7)
"Really nice area. I will be returning. Very nice. Thank you!"
United States
Bruce G.
The price is ￥12,982
￥29,684 total
includes taxes & fees
Nov 17 - Nov 18
Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville
Dining
Cottage near the Bay

Cottage near the Bay

Crisfield
8.8 out of 10, Excellent, (50)
"We had a great time! Everything went smoothly from beginning to end! We would definitely stay here again. "
United States
Jennifer J.
The price is ￥12,519
￥28,997 total
includes taxes & fees
Nov 16 - Nov 17
Cottage near the Bay
Smart TV
Newly updated 3 bedroom cottage with Solo Stove fire pit

Newly updated 3 bedroom cottage with Solo Stove fire pit

Reedville
9.8 out of 10, Exceptional, (17)
"This was a nice quiet place for family to enjoy."
United States
Terry S.
The price is ￥13,631
￥37,509 total
includes taxes & fees
Nov 16 - Nov 17
Newly updated 3 bedroom cottage with Solo Stove fire pit
Smart TV, books
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, (8)
"I had a wonderful stay at this cozy waterfront cottage. The listing was accurate, and the serene setting made for a relaxing getaway. The home was clean, well-equipped, and the views were stunning. We especially enjoyed watching the deer and fiddler crabs. Highly recommend for a peaceful retreat."
United States
Antwoine S.
The price is ￥24,728
￥54,953 total
includes taxes & fees
Nov 30 - Dec 1
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Beach
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
The price is ￥14,682
￥31,618 total
includes taxes & fees
Nov 22 - Nov 23
Tangier Escape, great place get away from it all on Deal Island, MD.
Exterior detail
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, (26)
"Wonderful property! Great communication!"
United States
Lauren W.
The price is ￥23,646
￥56,383 total
includes taxes & fees
Nov 24 - Nov 25
Reelin&Relaxin Spacious Farmhouse Reedville, VA Sleeps 8: 3 Bdrm 2 full bathroom
1 bedroom, WiFi, bed sheets
Kentigern Shed at Scotland Yards

Kentigern Shed at Scotland Yards

Point Lookout
9.6 out of 10, Exceptional, (155)
"Interesting layout. Bed is small. Nice to be able to bring our dog. "
United States
Jackie O.
The price is ￥28,128
￥52,457 total
includes taxes & fees
Nov 16 - Nov 17
Kentigern Shed at Scotland Yards
Outdoor dining
Bayfront Oasis with Heated Pool, Hot Tub & Playground! Family & Pet friendly!

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

Reedville
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 ￥84,492
￥175,567 total
includes taxes & fees
Nov 17 - Nov 18
Bayfront Oasis with Heated Pool, Hot Tub & Playground! Family & Pet friendly!
Outdoor dining
Luxury 4-Bedroom Waterfront Beachfront Home with Bay Views & Spa

Luxury 4-Bedroom Waterfront Beachfront Home with Bay Views & Spa

2.0 star property
Point Lookout
The price is ￥62,933
￥125,926 total
includes taxes & fees
Nov 19 - Nov 20
Luxury 4-Bedroom Waterfront Beachfront Home with Bay Views & Spa
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Smith Island Hotel Reviews

Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!

Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!

10/10 Excellent
"Beautiful house with great views, fantastic amenities. "
Monica 3-night trip
Posted 5 days ago
Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!

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?

Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart: Visitors like this Smith Island vacation home rental. It 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.

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.