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, (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!

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

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 NZ$584
includes taxes & fees
17 Aug - 18 Aug
Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart

Pet-Friendly Smith Island Cottage w/ Golf Cart!

9.8 out of 10, Exceptional, (19)
"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!

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

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

Cottage near the Bay

9.0 out of 10, Wonderful, (43)
"great, peaceful "
The price is NZ$317
includes taxes & fees
18 Aug - 19 Aug
Cottage near the Bay

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

9.6 out of 10, Exceptional, (92)
"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!

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

Private Beach Front Getaway at The Sunshine Beach Cottage.

9.8 out of 10, Exceptional, (72)
"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.

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

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

BEACH COTTAGE BY THE SEA....

9.8 out of 10, Exceptional, (30)
"A beautiful little cottage with a beautiful beach front access and plenty of amenities."
BEACH COTTAGE BY THE SEA....

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

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

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

Walk to Main Street: Family-Friendly Crisfield Gem

10.0 out of 10, Exceptional, (2)
"Beautiful property"
Walk to Main Street: Family-Friendly Crisfield Gem

"Gull Cottage" Charming Tiny House on Chesapeake Bay-Boat Launch/Slip included

9.8 out of 10, Exceptional, (67)
"We made last minute plans and were happy with our decision to stay at Mary’s place. It was big enough for our family including our two teenage daughters. The location is quiet and peaceful. The home was clean and had everything we needed!"
"Gull Cottage" Charming Tiny House on Chesapeake Bay-Boat Launch/Slip included

'River's Edge Retreat’ with Kayaks & River Access!

9.6 out of 10, Exceptional, (61)
"Group outing went flawless with this spacious pad. Plenty of room to accommodate our group."
'River's Edge Retreat’ with Kayaks & River Access!

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

9.6 out of 10, Exceptional, (50)
"We had a great time for a fishing weekend. Place was clean and comfortable. Hosts were amazing. Location for fishing is very convenient."
"Heron's Nest" Charming Tiny House on Chesapeake Bay-Boat Launch/Slip Included

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

10.0 out of 10, Exceptional, (70)
"Nice property, clean. Perfect for a getaway !"
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, (38)
"Adorable home with an amazing view from any window! We kayaked right from the dock. The view is why you stay here! Breathtaking! Management responded quickly. We would definitely stay again and recommend to anyone who loves the water and views. "
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10
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 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?

Historic home on Smith Island w/ dock!: This highly rated holiday home rental in Smith Island is located on the waterfront, and has a patio, a private garden and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of books. Our travellers also rate Spacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island as a favourite home for rent in Smith Island.

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 J. Millard Tawes Museum.

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.