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, (45)
"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, (18)
"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

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

9.8 out of 10, Exceptional, (13)
"The perfect place to wind down, reconnect with people, culture and a way of life we’ve strayed away from. The house was amazing! The town, the good people and the atmosphere just as much. "
The price is AU$535
includes taxes & fees
28 Sept - 29 Sept
Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart

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, (47)
"great, peaceful "
The price is AU$288
includes taxes & fees
1 Oct - 2 Oct
Cottage near the Bay

FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS

10.0 out of 10, Exceptional, (192)
"Great for our group of 2 families. Plenty of beds, nice gathering space, access to the creek, played in the grassy field. Would/will likely return! "
FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS

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

9.6 out of 10, Exceptional, (94)
"We all really enjoyed our long weekend at this property outside Reedville, VA. The pool was a highlight! Property is in good condition overall, if a bit dated, and located in a very quiet residential area. The house is compact and best fit for 2-3 people, and older kids since the interior stairs are steep and there is a lot of water nearby. "
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, (122)
"We are not strangers to the area, my wife having grown up in the area, but each time we stay on the Chesapeake we feel at home. The Hideaway is so nice that you don't want to go back your actual home! It is furnished as if it is a year-round residence, no cheap or mismatched furniture and appliances. We enjoy cooking and the kitchen is has everything you need and it works. The yard and amenities are top notch. If you enjoy bird watching, sit in the back yard and take in the bird activity...
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach

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."
The price is AU$325
includes taxes & fees
9 Oct - 10 Oct
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

BEACH COTTAGE BY THE SEA....

10.0 out of 10, Exceptional, (31)
"The house is small, but works great for a getaway and has everything you need. We spent most of our time at the beach or on the deck -- so peaceful! "
BEACH COTTAGE BY THE SEA....

Private, Waterfront, Ultra-clean, Pet friendly, Kayaks, Canoe, Firepit, more!

10.0 out of 10, Exceptional, (218)
"Went for spring break - weather was colder than we hoped for but a beautiful property with all the amenities! Very peaceful, owners attentive. Would definitely go back again!"
Private, Waterfront, Ultra-clean, Pet friendly, Kayaks, Canoe, Firepit, more!

Bay Front Small Contemporary

9.8 out of 10, Exceptional, (112)
"Nice property with incredible views!"
Bay Front Small Contemporary

"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

Private Beach Front Getaway at The Sunshine Beach Cottage.

9.8 out of 10, Exceptional, (76)
"We had a lovely stay at the Sunshine Beach Cottage - it was just as we expected and easy to check in and out. We look forward to the next time we can stay! "
Private Beach Front Getaway at The Sunshine Beach Cottage.

Summerlee at Scotland Yards

9.8 out of 10, Exceptional, (107)
"Perfect size house for the family with comfortable beds, spectacular views and very private location! Definitely would like to return."
Summerlee at Scotland Yards

Beautiful Bayfront with Sanctuary Private Beach

9.2 out of 10, Wonderful, (24)
"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

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

9.8 out of 10, Exceptional, (9)
"We enjoyed our family vacation, so relaxing and accommodating. Loved the location and setup. "
Private 5-acre Waterfront Retreat with Main & Guest House & BBQ Shed

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

9.6 out of 10, Exceptional, (42)
"The property was Beautiful and very clean. The Owner was very helpful and responsive even for s last minute change. "
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10

𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻 𝐇𝐀𝐘𝐒 𝐁𝐄𝐀𝐂𝐇 step of your porch into the sand 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘

10.0 out of 10, Exceptional, (124)
"Host is awesome, available to answer questions and just excited for her guests to enjoy their stay! "
𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻 𝐇𝐀𝐘𝐒 𝐁𝐄𝐀𝐂𝐇 step of your porch into the sand 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘
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

Find out more about Smith Island

Find out more about Smith Island

Everything you need to know about Smith Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Smith Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Smith Island holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Smith Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Smith Island holiday rentals we have selected for you start as low as AU$288 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Smith Island rentals

At Expedia, we put the best Smith Island holiday 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 holiday.

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 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 Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart as a favourite home for rent in Smith Island.

How many holiday rentals are there in Smith Island?

With 7 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.