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, (46)
"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, (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 NZ$593
includes taxes & fees
7 Oct - 8 Oct
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

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

9.6 out of 10, Exceptional, (94)
"We had a nice quiet week in this adorable and clean home just relaxing in the pool and spending time in the kayaks. We ventured out for some yummy Mexican food for dinner, ice cream in Reedville, and the nearby cafe to try their cappuccino and breakfasts but otherwise spent a nice family week playing games and swimming. "
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, (123)
"Really enjoyed our time here. The outdoor space in the back was great with the swing and the fire pits. Our kids loved walking to the beach everyday and catching crabs. "
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach

FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS

10.0 out of 10, Exceptional, (193)
"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

Cottage near the Bay

8.8 out of 10, Excellent, (49)
"great, peaceful "
The price is NZ$320
includes taxes & fees
16 Oct - 17 Oct
Cottage near the Bay

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

2.0 star property
8.0 out of 10, Very good, (5)
"Really nice area. I will be returning. Very nice. Thank you!"
The price is NZ$313
includes taxes & fees
7 Oct - 8 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

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.

BEACH COTTAGE BY THE SEA....

10.0 out of 10, Exceptional, (32)
"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, (113)
"Nice property with incredible views!"
Bay Front Small Contemporary

Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!

9.8 out of 10, Exceptional, (56)
"We had a great time kayaking, fishing, catching crabs and eating outside with our family under the picnic table. We didn’t get a chance to use the firepit but we really appreciate that there are firewood available to use. The house is was perfect for my family. I’m glad that even though it’s an older home, the bathrooms and bedrooms were updated. My mom and sisters who came with us really enjoyed the stay too. The host were great and awesome too. Quick on responding too."
Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!

Summerlee at Scotland Yards

9.8 out of 10, Exceptional, (108)
"Perfect size house for the family with comfortable beds, spectacular views and very private location! Definitely would like to return."
Summerlee at Scotland Yards

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)
"Beautiful cottage! Sun, sand, crabbing, kayaking"
𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻 𝐇𝐀𝐘𝐒 𝐁𝐄𝐀𝐂𝐇 step of your porch into the sand 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘

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

10.0 out of 10, Exceptional, (73)
"This was our second year vacationing at this property. The Owner does a good job...very responsive. Plenty of pool toys, grills, cooking utensils for all grills, a crab pot. Crabbing is great. Many fun inside games (our week was very hot). Takes care of pool and trash daily. Always upgrading the property. Enabled our multi-generational family to reconnect. It's great. Highly recommend. "
When you want to get away from everything Magnolia shores 2 acres of tranquility

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

9.6 out of 10, Exceptional, (127)
"Great location for summer afternoon breeze. "
Waterfront Cottage On Candy Point: Family-Friendly and Dog-Friendly!

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

3.0 star property
'river's Edge Retreat With Kayaks & River Access!
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 favorite 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 depends 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 NZ$313 per night. Entering your travel dates in the search wizard you might find 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.

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 Crisfield City Dock.

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.