Eastport holiday lettings

We found 183 holiday rentals — enter your dates for availability

Discover a selection of 53 homes, 12 apartments and other holiday rentals in Eastport that are perfect for your trip. Holiday homes offer the amenities that you expect for your family, friends or furry companion, such as parking and air conditioning. No matter what you're looking for, you're sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

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Frequently asked questions

What is the most popular type of holiday rental in Eastport?
In Eastport, holiday houses are the most prevalent type of rental, with around 30 available in the area. These homes often provide spacious living environments, complete with multiple bedrooms, fully equipped kitchens, and outdoor spaces for relaxation, making them ideal for families or groups. Additionally, there are several condos and apartments, which typically include modern amenities such as kitchen facilities and comfortable living areas, suiting those seeking a more compact stay. For a great experience, several cottages and houseboats can also be found, offering charming accommodations close to the waterfront and local attractions.
Are there any beach house rentals in Eastport?
In Eastport, Maryland, there are several beach house rentals available, providing a charming getaway near the waterfront. These properties are typically located in picturesque neighbourhoods, allowing guests easy access to the nearby Annapolis Harbour and the vibrant downtown area. Most beach houses come equipped with modern amenities such as fully stocked kitchens, spacious living areas, and outdoor decks or patios, superb for enjoying the pleasant Maryland weather. Many also feature multiple bedrooms, making them ideal for families or groups looking to spend quality time together while being close to local attractions like the Eastport Yacht Club and various waterfront dining options.
How much does it cost to rent a holiday home in Eastport?
Prices for holiday rentals in Eastport 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Eastport to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Eastport holiday house rentals?
You can find great discounts on house rentals in Eastport on Vrbo, 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.
Are there any Eastport holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Eastport 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 on Vrbo 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.
Can I find long-stay holiday rentals in Eastport?
A long-stay holiday rental in Eastport 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Eastport for a holiday rental?
July is the most popular month to visit Eastport, as it falls within the peak season that runs from May to July. During this lively period, visitors flock to the area to enjoy the warm summer temperatures, which typically hover around the mid-20s Celsius. This is an ideal time for those seeking outdoor activities, such as sailing, kayaking, or simply relaxing by the waterfront, all while soaking in the vibrant local culture.

The charming streets of Eastport come alive with festivals, art shows, and an array of dining options that cater to a variety of tastes. The bustling atmosphere is superb for travellers looking to mingle with fellow holidaymakers while enjoying the scenic beauty of the Chesapeake Bay.

For those seeking a more budget-friendly experience, consider planning your visit in December. While this month may be quieter, it offers a unique opportunity to explore Eastport's festive holiday events and enjoy the peaceful charm of the off-peak season. The winter scenery can be quite picturesque, creating a lovely backdrop for leisurely strolls and cosy evenings.
Are there any remote work holiday rentals in Eastport?
In Eastport, Maryland, there are plenty of remote work-friendly holiday rentals available, with around 42 options to choose from. This charming waterfront community, located near Annapolis, offers a range of properties that cater to those looking to combine work and leisure. Many of these rentals are equipped with essential amenities such as high-speed Wi-Fi, dedicated desks, and comfortable office chairs, providing an ideal environment for productivity. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Eastport holiday rental?
Book your Eastport holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Eastport?
In Eastport, Maryland, visitors can enjoy a variety of attractions that showcase the area's maritime charm and local culture. The Eastport Historic District is a delightful area to explore, featuring quaint streets lined with colourful homes and independent shops. The Annapolis Maritime Museum offers insights into the region's rich boating history and maritime heritage, making it a must-visit for those interested in local lore.

Nearby, the scenic waterfront at Eastport's Spa Creek provides beautiful views and opportunities for boating and kayaking. For a taste of local cuisine, the area is known for its seafood restaurants, many of which offer outdoor seating with views of the water. Additionally, the vibrant arts scene in Eastport is highlighted by galleries and studios showcasing local artists, making it a pleasant place for art enthusiasts to explore.
Can I change or cancel my Eastport home rental booking on Vrbo?
To find Eastport holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Eastport holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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