Smith Island holiday rentals

We found 20 holiday rentals — enter your dates for availability
Discover a selection of 7 homes and other holiday rentals in Smith Island that are perfect for your trip. Whether you're staying in a holiday rental with friends, family or just with your pet, you'll have the amenities that you expect and more, which might include a garden and pool. You're sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.

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    Enjoy full kitchens, laundry, pools, gardens and more

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The waterfront setting of Smith Island is ready to explore

The island views and other outdoor surroundings create an inviting atmosphere in Smith Island. This city has something for everyone. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Exploring the natural features in Smith Island

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Smith Island is a great place to get outside. Here are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Smith Island (0.9 mi / 1.4 km)
  • Tangier Island Beach (12 mi / 19.4 km)
  • Crab Island (15.5 mi / 25 km)
  • Terrapin Sand Point (3.7 mi / 5.9 km)
  • Cedar Island State Wildlife Management Area (9.1 mi / 14.7 km)
  • Jersey Island (9.4 mi / 15 km)

Frequently asked questions

What is the best area to stay in Smith Island when booking a holiday rental?
When considering the best area to stay on Smith Island, Maryland, a delightful choice is the community of Ewell. This charming area serves as the island's primary settlement and offers a unique glimpse into the local culture and way of life. Here, you can find a variety of holiday rentals, often characterised by their quaint, rustic charm.One of the top attractions in Ewell is the Smith Island Cake Company, where you can sample the famous layered cakes that the island is renowned for. Additionally, the nearby marshes and waterways provide excellent opportunities for kayaking and birdwatching, making it a superb spot for nature enthusiasts.Another top area is Tylerton, a smaller, more secluded village that boasts a tranquil atmosphere. It's an ideal choice for those seeking peace and quiet, with stunning views of the surrounding waters. Tylerton is also home to the beautiful Smith Island National Wildlife Refuge, where visitors can enjoy the serene landscapes and observe a variety of wildlife.
Where are the best areas for renting a beach house in Smith Island?
For renting a beach house in Smith Island, visitors should focus on the quaint communities of Ewell and Tylerton, which offer a serene escape surrounded by beautiful waterfront views. The area is known for its picturesque landscapes, with properties often situated right along the shoreline, providing easy access to the water. Many of these beach houses come equipped with essential amenities such as spacious decks or porches, superb for enjoying sunsets, as well as kitchens ideal for preparing fresh seafood caught locally.Ewell, being the largest community on Smith Island, features charming cottages and family homes that often have the added benefit of outdoor grills and picnic areas for alfresco dining. Guests can expect well-furnished interiors with comfortable living spaces, and some homes may even offer game rooms or activities for families.Tylerton, on the other hand, presents a more secluded option, ideal for those looking to escape the hustle and bustle. Here, rentals may include rustic cabins that embrace a more traditional island feel, often featuring wood-burning stoves, fishing gear, and access to kayaking or boating activities in the surrounding waters. The quiet atmosphere is complemented by the opportunity to explore local wildlife and nature reserves, making it a delightful spot for beach house rentals on Smith Island.
What is the most popular type of holiday rental accomodation in Smith Island?
In Smith Island, holiday houses and cottages are the most popular types of holiday rentals, with several options available throughout the island. These properties generally offer a charming and rustic experience, often featuring amenities such as fully equipped kitchens, comfortable living areas, and outdoor spaces to enjoy the tranquil surroundings. Many of these rentals are located near the waterfront, providing easy access to the island's natural beauty and scenic views.
Are there any family house rentals in Smith Island?
In Smith Island, there are several family-friendly house rentals available, making it an appealing destination for groups seeking a memorable getaway. The island is known for its charming communities and beautiful waterfront views, with properties often situated close to the shores of the Chesapeake Bay. Many homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play and enjoy the fresh air.Visitors can explore the local culture by wandering through the quaint streets of Ewell, the island's main settlement, and discovering the rich maritime history. With nearby points of interest such as the Smith Island Cake Company and opportunities for kayaking or fishing, families will find plenty to do during their stay.
Are there pet-friendly house rentals in Smith Island?
In Smith Island, there are several pet-friendly house rentals available, superb for travellers wishing to bring their furry companions along. The island offers a unique charm with its picturesque landscapes and rich maritime history. Many of the holiday rentals feature amenities such as fully equipped kitchens, spacious living areas, and outdoor decks where guests can relax and enjoy the serene surroundings.Visitors can explore the nearby Smith Island Heritage Trail, which presents opportunities for walking and enjoying nature while accommodating pets. The island's close-knit community and laid-back atmosphere make it an inviting destination for those looking to unwind with their pets by their side.
Are there any remote work holiday rentals in Smith Island?
In Smith Island, there are several holiday rentals available that cater to remote workers. These properties typically offer amenities such as free Wi-Fi, allowing you to stay connected while enjoying the tranquil surroundings. Many rentals provide comfortable living spaces, conducive for work, along with the possibility of hosting events if needed. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Smith Island?
In Smith Island, popular rental amenities include kitchens, which allow guests to prepare their own meals, and decks or patios that provide a lovely space for relaxation and enjoying the views of the surrounding area. Additionally, many rentals come equipped with a blender and a coffee or tea maker, suiting those who appreciate home comforts. Furthermore, some properties are pet-friendly, making it easier for travellers to bring their furry companions along for the stay.
What are the top attractions in Smith Island?
In Smith Island, visitors can experience firsthand the unique charm of this serene destination. The island is renowned for its picturesque landscapes and the rich heritage of its watermen community. One of the key attractions is the Smith Island Cake, a traditional dessert that can be found at local eateries, offering a sweet taste of the island's culture.The island's quaint villages, particularly Ewell and Tylerton, feature beautiful waterfront views and opportunities to observe local wildlife. Here, you can enjoy activities such as birdwatching and exploring the scenic marshes.For those interested in history, the Smith Island Museum provides insights into the island's maritime past and the lives of its residents. Additionally, the surrounding waters are great for kayaking and fishing, allowing visitors to experience the natural beauty of the Chesapeake Bay.
Are all fees included in the Smith Island holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Smith Island holiday homes with parking?
Stayz offers a wide selection of holiday homes in Smith Island with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Smith Island holiday homes?
You can find great discounts on holiday homes in Smith Island on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Smith Island holiday home booking on Stayz?
To find Smith Island holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Smith Island?
A long-stay holiday home in Smith Island is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Smith Island holiday home?
Book your Smith Island holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Smith Island?
Prices for holiday homes in Smith Island vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Smith Island to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.