Holiday Rentals in Smith Island

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Check prices for these dates

In two weeks
31 Oct - 2 Nov
In one month
14 Nov - 16 Nov
In two months
12 Dec - 14 Dec
In three months
9 Jan - 11 Jan

Holiday Rentals in Smith Island

Smart TV, fireplace, ping pong, books
Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart
Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart
9.8 out of 10, Exceptional, (14)
"The perfect place to wind down, reconnect with people, culture and a way of life weโ€™ve strayed away from. The house was amazing! The town, the good people and the atmosphere just as much. "
The price is โ‚ฌ307
includes taxes & fees
15 Oct - 16 Oct
Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart
Beach
Historic home on Smith Island w/ dock!
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!
Terrace/patio
Spacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island
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
Fridge, microwave, oven, stovetop
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach
10.0 out of 10, Exceptional, (124)
"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
Exterior
Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville
Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville
2.0 star property
8.4 out of 10, Very good, (6)
"Really nice area. I will be returning. Very nice. Thank you!"
The price is โ‚ฌ176
includes taxes & fees
15 Oct - 16 Oct
Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville
Outdoor dining
Near Chincoteague & Assateague Island Charming 2-bedroom cottage
Near Chincoteague & Assateague Island Charming 2-bedroom cottage
9.4 out of 10, Exceptional, (3)
"Lovely, small but cozy, great place to bond and enjoy good food and drink."
Near Chincoteague & Assateague Island Charming 2-bedroom cottage
Dining
Cottage near the Bay
Cottage near the Bay
8.8 out of 10, Excellent, (49)
"great, peaceful "
The price is โ‚ฌ167
includes taxes & fees
27 Oct - 28 Oct
Cottage near the Bay
On the beach, sun-loungers
Bay Front Small Contemporary
Bay Front Small Contemporary
9.8 out of 10, Exceptional, (113)
"Absolutely love this place!"
Bay Front Small Contemporary
Property grounds
"Dragonfly" Waterfront Cottage on Chesapeake Bay
"Dragonfly" Waterfront Cottage on Chesapeake Bay
2.5 star property
10.0 out of 10, Exceptional, (3)
"Great getaway location right on th4e water. Highly recommended"
"Dragonfly" Waterfront Cottage on Chesapeake Bay
On the beach, sun-loungers, beach towels
Private Beach Front Getaway at The Sunshine Beach Cottage.
Private Beach Front Getaway at The Sunshine Beach Cottage.
9.8 out of 10, Exceptional, (76)
"A charming and cozy cottage right on the water - caught and ate crabs every day and loved kayaking down the creek through the serene marshland!"
Private Beach Front Getaway at The Sunshine Beach Cottage.
Property grounds
BEACH COTTAGE BY THE SEA....
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....
Fridge, microwave, oven, stovetop
Private 5-acre Waterfront Retreat with Main & Guest House & BBQ Shed
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
Outdoor dining
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10
9.6 out of 10, Exceptional, (42)
"Lovely shade and plenty of space and fresh air. Donโ€™t miss out on doing the ferry (closed on Sundays I believe)"
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10
Property grounds
Private, Waterfront, Ultra-clean, Pet friendly, Kayaks, Canoe, Firepit, more!
Private, Waterfront, Ultra-clean, Pet friendly, Kayaks, Canoe, Firepit, more!
10.0 out of 10, Exceptional, (220)
"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!
Property grounds
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๐‘ฉ๐‘จ๐’€ ๐‘บ๐‘ฐ๐‘ซ๐‘ฌ ๐‘น๐‘ฌ๐‘ป๐‘น๐‘ฌ๐‘จ๐‘ป ๐‡๐€๐˜๐’ ๐๐„๐€๐‚๐‡ step of your porch into the sand ๐‚๐‡๐„๐’๐€๐๐„๐€๐Š๐„ ๐๐€๐˜
10.0 out of 10, Exceptional, (124)
"Beautiful cottage! Sun, sand, crabbing, kayaking"
๐‘ฉ๐‘จ๐’€ ๐‘บ๐‘ฐ๐‘ซ๐‘ฌ ๐‘น๐‘ฌ๐‘ป๐‘น๐‘ฌ๐‘จ๐‘ป ๐‡๐€๐˜๐’ ๐๐„๐€๐‚๐‡ step of your porch into the sand ๐‚๐‡๐„๐’๐€๐๐„๐€๐Š๐„ ๐๐€๐˜
Fridge, microwave, oven, stovetop
FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS
FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS
10.0 out of 10, Exceptional, (193)
"The property is beautiful and the house is so spacious! It was great being able to put our boat in at Buzzโ€™s Marina and dock it at the house. The hosts are wonderful and very accommodating. They were also quick to respond. Highly recommend! "
FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS
Interior
Entire 4-bedroom 2-bath Cabin with AC, Recreational rooms, WiFi in Crisfield, MD
Entire 4-bedroom 2-bath Cabin with AC, Recreational rooms, WiFi in Crisfield, MD
8.6 out of 10, Excellent, (4)
"Our stay was amazing. The cabin was exactly as described. 9 family member stayed at the cabin comfortably. The view of the lake was breathtaking, the property was quiet and inviting with plenty of space for celebrating. We came to attend the Crab and Cruise experience which was a short drive from tge property. The surrounding city was quaint and friendly."
Entire 4-bedroom 2-bath Cabin with AC, Recreational rooms, WiFi in Crisfield, MD
Games room
Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!
Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!
9.8 out of 10, Exceptional, (57)
"We had a great time kayaking, fishing, catching crabs and eating outside with our family under the picnic table. We didnโ€™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. Iโ€™m glad that even though itโ€™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!
Interior
Waterfront Cottage On Candy Point: Family-Friendly and Dog-Friendly!
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!
Exterior
"Heron's Nest" Charming Tiny House on Chesapeake Bay-Boat Launch/Slip Included
"Heron's Nest" Charming Tiny House on Chesapeake Bay-Boat Launch/Slip Included
9.6 out of 10, Exceptional, (52)
"Iโ€™ve stayed a number of times in one of their cottages, if youโ€™re a fisherman or sailor it has everything you need. Mary, Capt Billy and Tiffany all provide excellent service and provide a very convenient and great place to stay. Book a trip! "
"Heron's Nest" Charming Tiny House on Chesapeake Bay-Boat Launch/Slip Included
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

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

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

10/10 Excellent
"This was our first visit to Smith Island and the Double H was perfect. It was close to the ferry landing so getting there was very easy. The house was well appointed and felt like home as soon as we arrived. We enjoyed the quiet of the island and we were able to fully disconnect and relax Thank you for a great day."
Amanda W. 5-night trip
Posted 7 days ago
Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart

Find out more about Smith Island

Everything you need to know about Smith Island holiday rentals

Whether youโ€™re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, weโ€™ve got the Smith Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and onโ€ฆ and on!

Thereโ€™s just as wide a choice of amenities, too. Maybe youโ€™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.ย 

Smith Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Smith Island. If youโ€™re looking for a little peace, consider booking during the quieter months, such as ย . For more hustle and bustle, you may prefer to visit in .ย 

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 groupsย andย 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.โ€ฏ The selection of Smith Island holiday rentals we have selected for you start as low as โ‚ฌ167 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. Youโ€™ll always find a great deal with Expedia.ย 

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 wantโ€”and just like that, youโ€™ve built your dream Smith Island holiday.

If youโ€™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.ย 

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, youโ€™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.