Smith Island Holiday Rentals

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Holiday Rentals in Smith Island

Historic home on Smith Island w/ dock!

9.6 out of 10, Exceptional, (36)
"The location was perfect, our host was extremely responsive and helpful. Chris gave us tips and set us up with the ferry Captain. Even though the large restaurant was closed there are 2 chefs that prepare wonderful meals! The srore/museum was ooen go meet the sweet manager! Thank you Chris for a wonderful family vacation!"
Historic home on Smith Island w/ dock!

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

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

Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD

2.0 star property
9.6 out of 10, Exceptional, (4)
"Great house, attentive host, and a beautiful and quiet setting"
Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD

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

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

Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks

10.0 out of 10, Exceptional, (69)
"Property provides relaxation and entertainment for all ages. If you can think of it, it's already there. Clean, well-kept everything in working order. Will definitely consider a longer stay in the future. Thank you for this opportunity. "
Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks

Deal Island Bay Cottage

9.8 out of 10, Exceptional, (56)
"We got every year and stay here, it’s great! "
The price is AU$440
includes taxes & fees
9 Feb - 10 Feb
Deal Island Bay Cottage

Private Northern Neck Retreat on Chesapeake Bay and Taskmaker Creek.

10.0 out of 10, Exceptional, (14)
"Words can not describe the memories that were made at this beautiful home during the past week. The sunrises, sunsets, the conversations on the deck, the fun times on the water, having thanksgiving dinner in a beautiful dining room with incredible views, the list could go on. This is our second time staying here, and we can't recommend this house and owner, Peter, enough. An absolute pleasure to work with Peter and his family. Thank you for the memories!"
Private Northern Neck Retreat on Chesapeake Bay and Taskmaker Creek.

Hays Beach House - Hot Tub - Private Beach

10.0 out of 10, Exceptional, (4)
"We booked this bayside property for a short family vacation and the house and amenities were exactly what we needed during our time at Hays Beach. There were ample bedrooms and spaces for all of us to relax, the kitchen was well appointed. The beach in front of the house was perfect for our grandson to play in a small pool while the others lounged in chairs or were in the water directly in front of the house. The public beach was a short walk away and we enjoyed seeing all the wildlife on the...
Hays Beach House - Hot Tub - Private Beach

Pine Shore Beach House on the Chesapeake Bay w/ 170ft pier

10.0 out of 10, Exceptional, (36)
"We wanted a family vacation and looked for a place on Chesapeake Bay. My son and daughter found this place and we reserved it. The house is beautiful. Has everything one would want. The location is great although it’s a bit of a drive to anywhere. Our plan was to spend most of the time at the house and in the bay. However that didn’t happen. First the weather didn’t cooperate as it rained most of the week. In addition there was an invasion of jellyfish. They were terrible! My grandchildren were...
Pine Shore Beach House on the Chesapeake Bay w/ 170ft pier

Private Beach Front Getaway at The Sunshine Beach Cottage.

9.8 out of 10, Exceptional, (63)
"Beautifully appointed cottage. Literally right on the water. Quiet, serene and relaxing. Loved it and will be back!"
Private Beach Front Getaway at The Sunshine Beach Cottage.

Bay House with Amazing View & Swimming Pool (open May- Sept.)

9.8 out of 10, Exceptional, (116)
"It is a dream place; my family and I had a great time, thanks to Jenn's prompt response. It is a very comfortable place and well-equipped for whatever one needs. I'll try to look them up on Facebook to follow them. Thank you very much for everything; it is a beautiful place with amazing views "
Bay House with Amazing View & Swimming Pool (open May- Sept.)

When you want to get away from everything Magnolia shores 2 acres of tranquility

10.0 out of 10, Exceptional, (65)
"Great time with great hosts! "
When you want to get away from everything Magnolia shores 2 acres of tranquility

Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10

9.8 out of 10, Exceptional, (32)
"Very nice and quiet. We were there end of December. "
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10

Bay Estate by AvantStay | Waterfront, Private Pond

10.0 out of 10, Exceptional, (1)
"Such a beautiful house, very nice for family or friends get together."
Bay Estate by AvantStay | Waterfront, Private Pond

Beachy Maryland A-Frame: Steps to Chesapeake Bay!

9.8 out of 10, Exceptional, (9)
"I loved this sweet A frame home! Celebrated my 48th birthday with a girls' trip and we all loved it. Enjoyed fires and Christmas movies each night. House has a lot of space and is so comfortable. Loved the views of the Bay, particularly from the sunroom and porch. Found quite a bit of sea glass on the neighborhood beach, as well as at the house beach during low tide. Owner was incredibly responsive and went above and beyond. Great place. Would highly recommend. "
Beachy Maryland A-Frame: Steps to Chesapeake Bay!

Virginia Retreat on Wicomico River w/ Dock!

10.0 out of 10, Exceptional, (16)
"My mom didn’t want to leave. Beautiful family retreat. Quiet and restful. "
Virginia Retreat on Wicomico River w/ Dock!

Chesapeake Bay and Lakefront home with Private Beach

10.0 out of 10, Exceptional, (37)
"Amazing property and amenities! Loved every minute!"
Chesapeake Bay and Lakefront home with Private Beach

Waterfront Marion Station Retreat w/ Private Dock!

8.6 out of 10, Excellent, (4)
"Home offers breathtaking views of the bay. Plenty of space for two families with children. Would love to come back!"
Waterfront Marion Station Retreat w/ Private Dock!

Secluded River Front Cottage

9.4 out of 10, Exceptional, (3)
"The home and property are exactly as advertised. I loved being five minutes away from Point Lookout, the sunset views, and the waterfront. "
Secluded River Front Cottage

"Heron's Nest" Charming Tiny House on Chesapeake Bay-Boat Launch/Slip Included

9.6 out of 10, Exceptional, (49)
"We needed a last minute place to stay and Mary saved the day. The cleaning fee for a tiny place added on to the nightly fee was a bit high, but beggars can't be choosers!! "
"Heron's Nest" Charming Tiny House on Chesapeake Bay-Boat Launch/Slip Included
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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Other types of properties in Smith Island you may be interested in

Historic home on Smith Island w/ dock!

9.6 out of 10, Exceptional, (36)
"The location was perfect, our host was extremely responsive and helpful. Chris gave us tips and set us up with the ferry Captain. Even though the large restaurant was closed there are 2 chefs that prepare wonderful meals! The srore/museum was ooen go meet the sweet manager! Thank you Chris for a wonderful family vacation!"
Historic home on Smith Island w/ dock!

Pet-Friendly Smith Island Cottage w/ Golf Cart!

9.8 out of 10, Exceptional, (9)
"great but high tide problems to limit activity"
Pet-Friendly Smith Island Cottage w/ Golf Cart!

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

10.0 out of 10, Exceptional, (15)
"Micky and Kim were great hosts and the house was awesome. They were very accommodating. Will definitely be back! "
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
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.

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?

Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks: This holiday home rental outside of Smith Island is located on the beach, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Smith Island?

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

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.