Smith Island Holiday Rentals

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Holiday Rentals in Smith Island

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

Smith Island
9.8 out of 10, Exceptional, (15)
"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. "
United States
David
The price is AU$486
includes taxes & fees
15 Nov - 16 Nov
Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart

Historic home on Smith Island w/ dock!

Smith Island
9.6 out of 10, Exceptional, (46)
"The house is wonderful, quaint and comfortable.The hosts are the best. Responsive and beyond helpful."
United States
Harry L.
Historic home on Smith Island w/ dock!

Blue Anchor Cottage at Smith Island MD Quaint & Charming Beach Cottage

Smith Island
10.0 out of 10, Exceptional, (1)
"As many reviewers say, Smith Island is not a hot spot teaming with places to go. We knew this when booking. We brought our cameras, our water colors to paint, books, knitting, cards.... we had a WONDERFUL time. The cottage was beautiful and had everything we needed. The host even supplied us with board games and bug spray. We walked the length of the island several times and spent most mornings with our binoculars and cameras birding. If you want to relax and can entertain yourself it is a...
United States
Beatrice W.
Blue Anchor Cottage at Smith Island MD Quaint & Charming Beach Cottage

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

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...
United States
Brent E.
Spacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island

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

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

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

Reedville
9.8 out of 10, Exceptional, (62)
"Beautiful house with great views, fantastic amenities. "
United States
Monica
Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!

Near Chincoteague & Assateague Island Charming 2-bedroom cottage

Saxis
9.4 out of 10, Exceptional, (3)
"Lovely, small but cozy, great place to bond and enjoy good food and drink."
United States
Bob H.
Near Chincoteague & Assateague Island Charming 2-bedroom cottage

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

2.0 star property
Reedville
8.0 out of 10, Very good, (7)
"Really nice area. I will be returning. Very nice. Thank you!"
United States
Bruce G.
The price is AU$300
includes taxes & fees
16 Nov - 17 Nov
Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville

A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 1 Min Walk to Sand

Point Lookout
10.0 out of 10, Exceptional, (125)
"We had a fantastic stay at the Hideaway in Hays Beach. We were coming up to see our 93yr old Grandmother who lives about 45 minutes away. Our families rented two homes in the area and were able to enjoy our time with three generations that aren’t able to see each other often. The home was exactly as shown, perfectly decorated and incredibly well stocked! We’d absolutely come back!"
United States
Seth H.
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 1 Min Walk to Sand

Cottage near the Bay

Crisfield
8.8 out of 10, Excellent, (50)
"We had a great time! Everything went smoothly from beginning to end! We would definitely stay here again. "
United States
Jennifer J.
The price is AU$292
includes taxes & fees
25 Nov - 26 Nov
Cottage near the Bay

Newly updated 3 bedroom cottage with Solo Stove fire pit

Reedville
9.8 out of 10, Exceptional, (17)
"This was a nice quiet place for family to enjoy."
United States
Terry S.
The price is AU$368
includes taxes & fees
19 Nov - 20 Nov
Newly updated 3 bedroom cottage with Solo Stove fire pit

"Dragonfly" Waterfront Cottage on Chesapeake Bay

2.5 star property
Reedville
10.0 out of 10, Exceptional, (3)
"The perfect getaway for our little family. Our dog, Francesca absolutely loved lounging on the beach and exploring the property. We enjoyed kayaking in the morning, photographing birds on the water in the afternoon, and making s'mores by the fire at night. The location is incredibly relaxing and stunning. The house was clean, cozy, and we wish that we could have stayed forever. The hosts were great. We would love to come back- definitely worth the 6 hour trip from Pennsylvania. "
United States
Kaytlin L.
"Dragonfly" Waterfront Cottage on Chesapeake Bay

Bay Front Small Contemporary

Reedville
9.8 out of 10, Exceptional, (114)
"Great place with a spectacular view. Would definitely love to stay again!"
United States
Jasper W.
Bay Front Small Contemporary

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

Reedville
9.6 out of 10, Exceptional, (95)
"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. "
United States
Judine K.
Private infinity pool, plus your own dock, kayaks, and bikes on the waterfront!

Private Beach Front Getaway at The Sunshine Beach Cottage.

Point Lookout
9.8 out of 10, Exceptional, (80)
"Everything was as advertised. Clean and tidy. Easy to find. Had everything we needed while visiting some state parks. Kids loved the beach and already asked to go back"
United States
Erik S.
Private Beach Front Getaway at The Sunshine Beach Cottage.

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

Heathsville
9.6 out of 10, Exceptional, (42)
"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. "
United States
Lisa F.
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

Point Lookout
10.0 out of 10, Exceptional, (124)
"This was the perfect spot for our first vacation with our baby. Quiet, private, and fun! So glad we stayed. "
United States
Paige T.
𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻 𝐇𝐀𝐘𝐒 𝐁𝐄𝐀𝐂𝐇 step of your porch into the sand 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘

Deal Island Bay Cottage

Deal Island
9.6 out of 10, Exceptional, (57)
"Very nice house and close enough to go places but far enough to be peaceful."
United States
Larry F.
The price is AU$407
includes taxes & fees
16 Nov - 17 Nov
Deal Island Bay Cottage

Beautiful Bayfront with Sanctuary Private Beach

Saxis
9.2 out of 10, Wonderful, (24)
"We had a wonderful 4 days stay. The location is peaceful and quiet with beautiful views. The house was clean and the host communicated well. Would definetly stay again."
United States
katrina g.
Beautiful Bayfront with Sanctuary Private Beach

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

Reedville
10.0 out of 10, Exceptional, (223)
"Beautiful house, secluded and very private. Highly recommend"
United States
Riaan M.
Private, Waterfront, Ultra-clean, Pet friendly, Kayaks, Canoe, Firepit, more!
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

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$292 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?

Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart: This highly rated holiday home rental in Smith Island offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You can relax into your holiday with a garden and a selection of games.

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 Chesapeake Bay are a couple of lovely local spots to get outside and enjoy nature. Horse Hammock and Tylerton County Dock are other places to visit while you're in town.

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.