Smith Island Vacation Rentals

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Vacation Rentals in Smith Island

Historic home on Smith Island w/ dock!

9.6 out of 10, Exceptional, (43)
"This property was perfect for a family of 4. It was very clean, the kitchen was well stocked and the neighbors were amazing and helpful. Visit the arcade by the marina right before sunset!"
Historic home on Smith Island w/ dock!

IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

10.0 out of 10, Exceptional, (17)
"Took my grandson for a weekend trip to Smith Island to celebrate his HS graduation. My daughter, also, accompanied us, since I am a 90 year old "Grammy", and need some assistance. Our cottage was clean, comfortable and had all of our needs. The host, Kim, was extremely attentive, and made our dinner the night we arrived so we could just relax. I would highly recommend Idle Hour as the place to stay on Smith Island. Pat Reynolds, Ellicott City, MD"
The price is CA $218
CA $414 total
includes taxes & fees
Aug 3 - Aug 4
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

Pet-Friendly Smith Island Cottage w/ Golf Cart!

10.0 out of 10, Exceptional, (17)
"The island is a beautiful and peaceful. Everyone there is so friendly and helpful. The cottage was a very clean and comfortable place to stay. We had 3 adults and 2 huskies and the home was very spacious. It is close to the docks, restaurant, and grocery store. We enjoyed our stay. If you’re looking for a peaceful and relaxing getaway this is the place to go! "
Pet-Friendly Smith Island Cottage w/ Golf Cart!

Get away to relax on Smith Island in the Chesapeake Bay with golf cart included

9.8 out of 10, Exceptional, (11)
"Smith island is lovely! This house was perfectly located and furnished and the owner super helpful."
The price is CA $311
CA $478 total
includes taxes & fees
Aug 4 - Aug 5
Get away to relax on Smith Island in the Chesapeake Bay with golf cart included

Spacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island

10.0 out of 10, Exceptional, (1)
"Amazing adventure! Peaceful! Beautiful! Privacy! Gourmet Kitchen! The house is set back from the neighborhood on a large lot. The decks are new and comfortably furnished. We cooked breakfast and dinner for 3 days and the well-equipped kitchen was perfect. Our days started and ended with gourmet meals, on the deck, emersed in the salt marsh. We explored the creeks, guts, and islands all around Ewell, Rhodes Point and Tylerton. Rich and Dani helped coordinate a private charter boat to bring our...
Spacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island

A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach

10.0 out of 10, Exceptional, (117)
"It was a great stay!"
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach

Bay Front Small Contemporary

9.8 out of 10, Exceptional, (108)
"Perfect spot for a quiet Easter weekend with books and the sound of water while sitting in the Adirondack chairs each day. You won’t regret this stay, will definitely come back! "
Bay Front Small Contemporary

Cottage near the Bay

9.0 out of 10, Wonderful, (38)
"First time trying this style rental and I’m absolutely happy with the decision. The host was very accommodating and available to answer questions I had plenty of local information on hand to do things very family-friendly fun. "
The price is CA $112
CA $261 total
includes taxes & fees
Aug 3 - Aug 4
Cottage near the Bay

Private infinity pool, plus your own dock, kayaks, and bikes on the waterfront!

9.6 out of 10, Exceptional, (90)
"This is a wonderful property to visit. It was in a great location with beautiful views. The property is clean, the host was friendly and accommodating. It is a location that I would definitely recommend and go back to visit again."
Private infinity pool, plus your own dock, kayaks, and bikes on the waterfront!

'river's Edge Retreat With Kayaks & River Access!

3.0 star property
'river's Edge Retreat With Kayaks & River Access!

Beautiful Bayfront with Sanctuary Private Beach

9.2 out of 10, Wonderful, (20)
"The property is beautiful and it was so nice to be so close to the water. Sunset view and fire pit out back were fun bonuses. Everything went smoothly and as expected. We enjoyed our stay, thank you!"
Beautiful Bayfront with Sanctuary Private Beach

Hays Beach House - Hot Tub - Private Beach

9.6 out of 10, Exceptional, (8)
"Stayed with two other families for the State Swim Championships. Property is spacious, clean and well appointed. Even the kitchen knives were sharp!"
Hays Beach House - Hot Tub - Private Beach

Waterfront Getaway: Kayaks, Paddle Board, Fishing!

10.0 out of 10, Exceptional, (15)
"Very nice, would definitely come back thanks "
Waterfront Getaway: Kayaks, Paddle Board, Fishing!

Private Beach Front Getaway at The Sunshine Beach Cottage.

9.8 out of 10, Exceptional, (71)
"If you want to relax by the water and getaway from the hustle and bustle, this is the place. The cottage is updated and cozy with amazing views. Just step off the patio onto the sand. Cottage was stocked with essentials and extra goodies to make it feel like home."
Private Beach Front Getaway at The Sunshine Beach Cottage.

BEACH COTTAGE BY THE SEA....

9.8 out of 10, Exceptional, (29)
"A beautiful little cottage with a beautiful beach front access and plenty of amenities."
BEACH COTTAGE BY THE SEA....

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

9.6 out of 10, Exceptional, (4)
"The house was close to family in the area, so location was great. The house was clean and airy. The door lock was a bit tricky - otherwise all was excellent."
The price is CA $207
CA $473 total
includes taxes & fees
Aug 3 - Aug 4
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

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

2.0 star property
8.0 out of 10, Very good, (5)
"I did do some cooking and did not find a sheet pan."
Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville

Near Chincoteague & Assateague Island Charming 2-bedroom cottage

10.0 out of 10, Exceptional, (1)
"very clean and neat, quiet. just what i needed"
Near Chincoteague & Assateague Island Charming 2-bedroom cottage

Walk to Main Street: Family-Friendly Crisfield Gem

10.0 out of 10, Exceptional, (1)
"Beautiful property"
Walk to Main Street: Family-Friendly Crisfield Gem

Private 5-acre Waterfront Retreat with Main & Guest House & BBQ Shed

10.0 out of 10, Exceptional, (5)
"We stayed for a long easter weekend getaway. It was a random pick on the map for a location choice. We had a great time with many memories made. Our kids (age range 16-21) loved the location and water front access. The crab pots and kayacks made available were a hit. Though we never caight a fish or crab, the ongoing tries never failed. From the moment we booked and arrived the host was easy to communicate with. The house and guest house were just as described. Every little touch was perfect....
Private 5-acre Waterfront Retreat with Main & Guest House & BBQ Shed
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

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 Spacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island as a favorite home for rent in Smith Island.

How many vacation rentals are there in Smith Island?

With 6 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 Horse Hammock are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find Tylerton County Dock and Crisfield City Dock.

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.