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, (37)
"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!

Pet-Friendly Smith Island Cottage w/ Golf Cart!

10.0 out of 10, Exceptional, (15)
"great but high tide problems to limit activity"
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, (7)
"Smith island is lovely! This house was perfectly located and furnished and the owner super helpful."
The price is NZ$433
includes taxes & fees
1 July - 2 July
Get away to relax on Smith Island in the Chesapeake Bay with golf cart included

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

10.0 out of 10, Exceptional, (16)
"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

8.8 out of 10, Excellent, (35)
"We enjoyed our stay. The host was very responsive to our needs and I appreciate her flexible schedule"
The price is NZ$312
includes taxes & fees
2 July - 3 July
Cottage near the Bay

Private Beach Front Getaway at The Sunshine Beach Cottage.

9.8 out of 10, Exceptional, (69)
"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 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻 𝐇𝐀𝐘𝐒 𝐁𝐄𝐀𝐂𝐇 step of your porch into the sand 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘

10.0 out of 10, Exceptional, (113)
"Wonderful stay with attentive host."
𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻 𝐇𝐀𝐘𝐒 𝐁𝐄𝐀𝐂𝐇 step of your porch into the sand 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘

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

9.8 out of 10, Exceptional, (35)
"Very nice and quiet. We were there end of December. "
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10

**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**

10.0 out of 10, Exceptional, (188)
"We were staying in town for an event at St. Mary’s College of MD. This beautiful property is only just over 10 minutes away and is nestled back on a beautiful creek. "
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**

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

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

1 min Walk to Beach: The Hideaway in Hays Beach - Chesapeake Bay 301-250-8384

10.0 out of 10, Exceptional, (114)
"It was a great stay!"
1 min Walk to Beach: The Hideaway in Hays Beach - Chesapeake Bay 301-250-8384

Walk to Main Street: Family-Friendly Crisfield Gem

Walk to Main Street: Family-Friendly Crisfield Gem

Near Chincoteague & Assateague Island Charming 2-bedroom cottage

Near Chincoteague & Assateague Island Charming 2-bedroom cottage

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

2.0 star property
6.0 out of 10, (2)
"I did do some cooking and did not find a sheet pan."
The price is NZ$362
includes taxes & fees
11 July - 12 July
Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville

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

9.6 out of 10, Exceptional, (86)
"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!

July 4th available! Waterfront getaway! Fish and crab from private dock!

10.0 out of 10, Exceptional, (46)
"Our stay at Sunrise Point was fantastic. The location, property and home were absolutely lovely with everything we needed and our host was great. We can wait to come back!!"
July 4th available! Waterfront getaway! Fish and crab from private dock!

Waterfront Cottage On Candy Point: Family-Friendly and Dog-Friendly!

9.6 out of 10, Exceptional, (123)
"Beautiful location in a great setting to spend time with family. So appreciated that the house was pet friendly and the neighbors were so nice."
Waterfront Cottage On Candy Point: Family-Friendly and Dog-Friendly!

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

9.8 out of 10, Exceptional, (117)
"Our two families had a wonderful time. The house had everything we could need and was wonderfully relaxing."
Bay House with Amazing View & Swimming Pool (open May- Sept.)

Waterfront Getaway: Kayaks, Paddle Board, Fishing!

10.0 out of 10, Exceptional, (12)
"Very nice, would definitely come back thanks "
The price is NZ$856
includes taxes & fees
6 July - 7 July
Waterfront Getaway: Kayaks, Paddle Board, Fishing!
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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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 Get away to relax on Smith Island in the Chesapeake Bay with golf cart included 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 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.