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
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Smith Island vacation rentals

A wooden cabin with a deck, a grill, and string lights.

1. Historic home on Smith Island w/ dock!

Historic home on Smith Island w/ dock!
Smith Island
9.6 out of 10, Exceptional, (52 reviews)
"Great place on Smith Island. Amazing community feeling for 48 hours. The ferry is super expensive (it was 25 per person each way ,so 50 total per person!!!), adding 250 to the entire visit for 5, so something to really consider. The island is beautiful, house was perfect, very quiet and well kept. No downsides, but not tons of activities for very active teenagers. Everything super easy in terms of house/info/check in and out."
United States
Nina Z.
$285 nightly
The price is $302
Sep 7 - Sep 8
Total with taxes and fees
Historic home on Smith Island w/ dock!
A marina at sunset with boats docked and buildings in the background.

2. The end of summer is here on Smith Island! Come out for some peace and quiet!

The end of summer is here on Smith Island! Come out for some peace and quiet!
Smith Island
9.8 out of 10, Exceptional, (15 reviews)
"Visiting with locals, fresh steamed crabs, simply enjoying the quiet island life"
United States
Samantha J.
$310 nightly
The price is $342
Sep 7 - Sep 8
Total with taxes and fees
The end of summer is here on Smith Island! Come out for some peace and quiet!
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, (61 reviews)
"Quiet area, the place needs to be cleaned, bedding changed, redo the bathroom"
United States
Pamela
$179 nightly
The price is $190
Aug 30 - Aug 31
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.
$235 nightly
The price is $249
Sep 2 - Sep 3
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, (19 reviews)
"Property is wonderful. It's a family home and they take excellent care of it. Be aware there are steep stairs to second floor, but deck and bay view sunsets are worth it. Bikes and kayaks are bonus."
United States
Diane S.
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, (24 reviews)
"Great place "
United States
Myranda R.
$252 nightly
The price is $270
Sep 1 - Sep 2
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
$332 nightly
The price is $356
Aug 27 - Aug 28
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, (60 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.
$249 nightly
The price is $264
Aug 27 - Aug 28
Total with taxes and fees
Deal Island Bay Cottage
A modern kitchen with wooden ceiling, white cabinets, stainless steel appliances, and a central island with seating.

9. Unique Tangier Cottage w/ Chesapeake Bay Views!

Unique Tangier Cottage w/ Chesapeake Bay Views!
3.0 star property
Tangier
Unique Tangier Cottage w/ Chesapeake Bay Views!
A spacious room with a high ceiling, large windows, a ceiling fan, a dining area with a table and chairs, and a sofa.

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
9.6 out of 10, Exceptional, (17 reviews)
"Was very cozy and comfortable."
United States
sandi c.
$408 nightly
The price is $450
Sep 21 - Sep 22
Total with taxes and fees
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
A spacious living area with a large glass door leading to an outdoor deck, ceiling fans, and a view of a lake.

11. Waterfront Getaway: Kayaks, Paddle Board, Fishing!

Waterfront Getaway: Kayaks, Paddle Board, Fishing!
Reedville
10.0 out of 10, Exceptional, (19 reviews)
"Wonderful stay and exactly as described. Friendly neighborhood."
United States
Drake D.
Waterfront Getaway: Kayaks, Paddle Board, Fishing!
A sunlit room with a sofa, a wooden table, and a dining area.

12. Hideaway in Hays Beach: Western Sandy Shore of Chesapeake Bay and 5g WiFi!

Hideaway in Hays Beach: Western Sandy Shore of Chesapeake Bay and 5g WiFi!
Point Lookout
10.0 out of 10, Exceptional, (138 reviews)
"Our family enjoyed our stay in this clean and comfortable cottage! The host was available to answer questions and the home was very well stocked with everything you could possibly need. Despite the rainy weather there was plenty of things for the kids to do. The back yard was beautifully landscaped with plenty of places to relax and enjoy nature! We will definitely return!"
United States
Kathy F.
Hideaway in Hays Beach: Western Sandy Shore of Chesapeake Bay and 5g WiFi!
A covered outdoor deck with a view of a lake, wooden furniture, and a ceiling fan.

13. 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.
$1,426 nightly
The price is $1,530
Sep 1 - Sep 2
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

Rodeway Inn at Somers Cove Marina

Rodeway Inn at Somers Cove Marina

10/10 Excellent
"Property well maintained. Pool clean. Staff quite helpful."
Susan 1-night trip
Posted 7 hours ago
Rodeway Inn at Somers Cove Marina

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 $270 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!: This highly rated vacation home rental in Smith Island 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. Our travelers also rate Summer is here on Smith Island! Come out and enjoy a great season on the Bay as a favorite home for rent in Smith Island.

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.