A person in a kayak on a calm body of water during sunset.

Smith Island Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Smith Island vacation rentals

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, (16 reviews)
"Visiting with locals, fresh steamed crabs, simply enjoying the quiet island life"
United States
Samantha J.
$297 nightly
The price is $328
Oct 16 - Oct 17
Total with taxes and fees
Come out and enjoy Autumn at the HH Ranch on Smith Island.
A row of white houses by a lake with American flags.

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

Charming 2 Bedroom house in beautiful Smith Island Pet-Friendly Golf Cart
Smith Island
10.0 out of 10, Exceptional, (2 reviews)
"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."
United States
Margaret A.
$326 nightly
The price is $346
Oct 13 - Oct 14
Total with taxes and fees
Charming 2 Bedroom house in beautiful Smith Island Pet-Friendly Golf Cart
A room with a wooden bench, a lamp, a wicker basket, and a window with sheer curtains.

3. Cottage near the Bay

Cottage near the Bay
Crisfield
8.6 out of 10, Excellent, (63 reviews)
"Quiet area, the place needs to be cleaned, bedding changed, redo the bathroom"
United States
Pamela
$176 nightly
The price is $187
Oct 12 - Oct 13
Total with taxes and fees
Cottage near the Bay
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.
$232 nightly
The price is $246
Oct 17 - Oct 18
Total with taxes and fees
Tangier Escape, great place get away from it all on Deal Island, MD.
A modern kitchen with wooden ceiling, white cabinets, stainless steel appliances, and a central island with seating.

5. Unique Tangier Cottage w/ Chesapeake Bay Views!

Unique Tangier Cottage w/ Chesapeake Bay Views!
Tangier
10.0 out of 10, Exceptional, (22 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.
$368 nightly
The price is $406
Oct 11 - Oct 12
Total with taxes and fees
Unique Tangier Cottage w/ Chesapeake Bay Views!
A bedroom with a bed, bedside tables, a lamp, and a painting on the wall.

6. 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, (27 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.
$239 nightly
The price is $256
Oct 12 - Oct 13
Total with taxes and fees
Newly updated 3 bedroom cottage with Solo Stove fire pit
A white door with a glass panel and a sunflower decoration, flanked by two wall-mounted lanterns.

7. 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 traveler
$347 nightly
The price is $372
Oct 12 - Oct 13
Total with taxes and fees
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.

8. Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (62 reviews)
"We loved this place! We were in town for baseball. It is very nice and has all the comforts of home. Kitchen big and well equipped, house was clean and very well furnished. Nice bathrooms and a lovely screened in back porch. It is very near a beautiful beach on the bay that has some of the most beautiful sunsets you will ever see. We really enjoyed this perk!! Prompt communication and everything was as described. I highly recommend this rental!!"
United States
Harold B.
$243 nightly
The price is $257
Oct 12 - Oct 13
Total with taxes and fees
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.

9. 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, (20 reviews)
"Was very cozy and comfortable."
United States
sandi c.
$398 nightly
The price is $440
Oct 26 - Oct 27
Total with taxes and fees
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
A modern kitchen with wooden ceiling, white cabinets, stainless steel appliances, and a central island with seating.

10. Unique Tangier Cottage w/ Chesapeake Bay Views!

Unique Tangier Cottage w/ Chesapeake Bay Views!
3.0 star property
Tangier
$358 nightly
The price is $395
Oct 11 - Oct 12
Total with taxes and fees
Unique Tangier Cottage w/ Chesapeake Bay Views!
A covered outdoor deck with a view of a lake, wooden furniture, and a ceiling fan.

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.
$1,298 nightly
The price is $1,393
Oct 13 - Oct 14
Total with taxes and fees
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

Historic home on Smith Island w/ dock!

Historic home on Smith Island w/ dock!

10/10 Excellent
"We had a wonderful stay! The thoughtful renovation and charming decorative touches made the property feel special. We truly enjoyed our time here and would happily stay again if we return to Smith Island."
Michael N. 1-night trip
Posted 6 days ago
Historic home on Smith Island w/ dock!

Find out more about Smith Island

Everything you need to know about Smith Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Smith Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Smith Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Smith Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Smith Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Smith Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $187 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Smith Island rentals

At Expedia, we put the best Smith Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Smith Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Smith Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Smith Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.