Eastport vacation rentals

We found 178 vacation rentals — enter your dates for availability

Discover a selection of 50 homes, 11 apartments, and other vacation rentals in Eastport that are perfect for your trip. Vacation homes provide the amenities you need and want for your family, friends, or furry companion, such as air conditioning and a pool. At the end of the day, you'll be able to choose a rental that has what everyone needs, including accessible or non-smoking choices.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Eastport

Why visit Eastport

  • Scenic Marina: Enjoy picturesque views and waterfront activities at Eastport's charming marina.
  • Historic Charm: Explore historic houses and local culture that reflect Eastport's rich heritage.
  • Outdoor Adventures: Participate in various family-friendly outdoor activities in urban parks.
  • Vibrant Downtown: Discover great dining and historical sites in nearby downtown Annapolis.
  • Diverse Accommodations: Choose from cozy cottages, vacation homes, and comfortable rentals for a memorable stay.

Popular types of accommodation around Eastport

Planning a getaway to Eastport? The next exciting step is selecting your perfect accommodation. Discover a variety of options including houses, cozy cottages, and comfortable apartment rentals. Whether you’re searching for a friendly house rental or a charming retreat, Eastport has something to suit every traveler's needs. Explore your choices and make your stay unforgettable.

  • Houses: The top choice for visitors in Eastport, these homes offer spacious and comfortable stays for families or friends.
  • Cottages: These quaint and charming accommodations provide a cozy atmosphere, ideal for a relaxing getaway.
  • Apartments: Convenient and modern, apartments are perfect for travelers seeking a home-like experience during their stay.
  • Condos: Offering great amenities and often stunning views, condos are a popular choice for vacationers.
  • House Boats: For a unique experience, consider staying on a houseboat, combining comfort with waterfront living.**

Top attractions near Eastport

Eastport, Annapolis, offers a delightful vacation experience perfect for families and outdoor enthusiasts. Visitors can explore urban parks, enjoy the scenic marina, and discover historic houses that reflect the area’s rich culture. Whether you're traveling solo or with loved ones, Eastport provides a variety of attractions that cater to those seeking both adventure and family-friendly activities in a vibrant city setting.

  • U.S. Naval Academy: This historic academy offers a glimpse into the naval traditions and training of future officers, featuring stunning architecture and beautiful grounds.
  • Chesapeake Bay Bridge: A marvel of modern engineering, this bridge provides spectacular views of the bay and connects you to the vibrant atmosphere of the surrounding cities.
  • Sandy Point State Park: A haven for outdoor enthusiasts, this park offers sandy beaches, hiking trails, and adventure activities amidst scenic natural beauty.

Things to do recommended for couples

For a romantic getaway in Eastport, enjoy sailing at the Annapolis Sailing School, just 0.4 miles away. Experience the elegance of the Ballet Theater of Maryland, only 1 mile from Eastport. Don't miss a wine tasting at Thanksgiving Farm Wines, located 11 miles away for a perfect evening.

Things to do recommended for families

Your family will have a blast at Navy-Marine Corps Memorial Stadium, only 2 miles from Eastport, enjoying the sports atmosphere. For more fun, head 4 miles to Annapolis Bowl for arcade adventures. Don't miss Fort Smallwood Park, 12 miles away, where you can unwind in a serene setting.

Things to do recommended for groups

Explore the Annapolis Mall Shopping Center for shopping and entertainment, enjoy a cultural evening at The Colonial Players theater, or hit the links at Annapolis Golf Club for a fun day outdoors. Each location offers a unique experience perfect for your group adventure.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Eastport

If you're traveling with a group, your family, pets, or planning for an extended stay, be sure to prioritize your filters accordingly. Here are some helpful booking tips for Vrbo.

  • Traveling to Eastport with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Eastport with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Eastport: For many families, a vacation isn't truly fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Eastport: If you're searching for vacation rentals with special rates for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to consider additional features like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Eastport

Eastport, a charming neighborhood of Annapolis, offers a delightful blend of waterfront views and family-friendly activities. Explore the vibrant downtown Annapolis, where historical sites and great dining options await. Take a scenic excursion to the Eastern Shore for a taste of local culture and beautiful landscapes. With its inviting atmosphere and friendly residents, Eastport is the perfect destination for outdoor adventures and memorable family experiences.

  • Annapolis: Situated in the heart of Maryland, Annapolis is a vibrant city known for its rich history and beautiful waterfront. As Eastport's neighboring area, it offers a mix of family-friendly activities and urban experiences. Visitors can explore the historic State House, enjoy shopping at local boutiques, or relax by the picturesque harbor. The city is also home to stunning landmarks such as the United States Naval Academy, scenic beaches, and serene lakes, making it an ideal destination for outdoor enthusiasts.
  • Historic District: Located just 0.9 miles from Eastport, the Historic District of Annapolis is a charming neighborhood steeped in colonial history. This area invites families and tourists to wander through its cobblestone streets lined with beautifully preserved 18th-century buildings. Visitors can enjoy a variety of shopping options, from local artisan shops to larger retail centers. Notable attractions include the Naval Academy, bustling tourist precincts, and the scenic dock port, where you can watch sailboats glide across the water.
  • Naval Academy: The Naval Academy village, situated 1 mile from Eastport, is an essential part of Annapolis's cultural fabric. This area is perfect for families looking to immerse themselves in military history and education. Besides visiting the impressive academy, you can explore nearby recreational areas and shopping venues. The neighborhood’s landmarks, including the tourist precinct and dock port, offer a unique blend of culture and outdoor activities, making it a delightful stop on your vacation itinerary.

Best time to go to Eastport

If you're planning a trip to Eastport, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April and June to July, while off-peak times, like February and November to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.6°F (2.0°C)Light RainMostly SunnyAverageSlightly Low
February37.9°F (3.3°C)Light RainMostly SunnySlightly LowSlightly Low
March44.6°F (7.0°C)Light RainMostly SunnyAverageSlightly Low
April55.0°F (12.8°C)Light RainMostly SunnySlightly HighAverage
May64.2°F (17.9°C)Light RainMostly SunnyAverageAverage
June73.0°F (22.8°C)Light RainMostly SunnySlightly HighAverage
July78.4°F (25.8°C)Light RainMostly SunnySlightly HighSlightly High
August76.8°F (24.9°C)Light RainMostly SunnyAverageSlightly High
September70.7°F (21.5°C)Light RainMostly SunnyAverageSlightly High
October60.4°F (15.8°C)Light RainMostly SunnyAverageAverage
November48.7°F (9.3°C)Light RainMostly SunnySlightly LowAverage
December41.5°F (5.3°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Plus, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental. We're here to help you make the most of your travel experience.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for you to create new travel plans, refine your existing itineraries, or manage your bookings. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To discover more about Trip Boards, please visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Eastport?
In Eastport, vacation houses are the most popular type of rental accommodation, with approximately 41 available throughout the area. These homes often feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups. Many also have outdoor spaces such as decks or patios, superb for enjoying the scenic views of the Chesapeake Bay. Additionally, there are several condos, apartments, and cottages available, providing a variety of options for travelers. Houseboats are also an interesting choice for those looking to experience life on the water.
Are there any beach house rentals in Eastport?
In Eastport, there are several beach house rentals available, providing a variety of options for travelers. These properties are primarily located near scenic waterfront areas, offering stunning views of the Chesapeake Bay and convenient access to local marinas and parks. Most beach houses come equipped with modern amenities such as fully stocked kitchens, spacious living areas, and outdoor decks or patios ideal for enjoying sunsets. Many also feature private docks, allowing guests to easily engage in water activities, such as boating or kayaking.
How much does it cost to rent a vacation home in Eastport?
Prices for vacation 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 vacation 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.
What are popular rental amenities in Eastport?
In Eastport, popular vacation rental amenities include fully equipped kitchens, allowing guests to prepare their own meals with ease. Many rentals feature decks or patios, great for enjoying the pleasant weather and scenic views of the surrounding area. Coffee and tea makers are commonly found in these properties, ensuring that travelers can start their mornings off right. Onsite parking is also a key amenity, making it convenient for those who may arrive by car.
Can I find family house rentals in Eastport?
In Eastport, Maryland, there are numerous family-friendly house rentals, with about 37 options available throughout the area. This charming waterfront community is great for families looking to enjoy a relaxing getaway. Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play and adults can unwind.

Visitors will appreciate amenities like Wi-Fi and air conditioning, ensuring a comfortable stay. The neighborhood is conveniently located near scenic spots such as the Annapolis Maritime Museum and the beautiful parks along the waterfront, offering various recreational opportunities.
Can I rent a vacation home with a pool or hot tub in Eastport?
In Eastport, Maryland, travelers will find a variety of vacation homes available for rent that feature pools and hot tubs, with around 12 options specifically offering pools. The area is known for its charming waterfront views and proximity to the bustling Annapolis, making it an ideal getaway. Many of these rentals come equipped with private pools and hot tubs, as well as outdoor spaces superb for relaxation and entertaining. Expect amenities like fully equipped kitchens, spacious living areas, and sometimes even access to docks for boating activities.
Are there any Eastport vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Eastport with parking available—perfect for families or travelers 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 book pet-friendly vacation rentals in Eastport?
Yes, you can book pet-friendly vacation rentals in Eastport, Maryland. This charming waterfront community offers a variety of vacation rentals that welcome pets, with around 21 options available to choose from. Many of these rentals feature amenities such as spacious backyards, outdoor patios, and cozy living areas, making them great for travelers with furry companions.

Eastport is known for its proximity to parks and scenic waterfront areas, ideal for walking your pet and enjoying the outdoors. Nearby, the Broadneck Park provides open green spaces and walking trails, ensuring plenty of opportunities for exercise and relaxation with your pet. Additionally, the vibrant downtown area of Annapolis, just a short drive away, is filled with pet-friendly cafes and shops, further enhancing your stay in this delightful region.
Can I find long-stay vacation rentals in Eastport?
A long-stay vacation rental in Eastport is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Eastport for a vacation rental?
The best time to book a vacation rental in Eastport is during the peak season from May to July, with July being particularly popular. This vibrant period draws travelers eager to enjoy the warm weather and participate in various outdoor activities, including sailing, kayaking, and exploring the charming waterfront.

In July, temperatures typically range from the mid-70s to mid-80s Fahrenheit, providing a pleasant climate for sightseeing and enjoying Eastport's picturesque scenery. The lively option is enhanced by local events, festivals, and bustling streets filled with shops and restaurants, making it a superb time for families and adventure-seekers alike.

For those looking for a more budget-friendly option, consider visiting in December. While this month is quieter, it offers a great experience with holiday festivities and a cozy winter charm. The town's decorations and local events can create a delightful atmosphere without the crowds, allowing for a more relaxed visit.

Ultimately, whether you prefer the excitement of summer or the tranquility of winter, Eastport has something special to offer all year round.
Are there any remote work vacation rentals in Eastport?
In Eastport, Maryland, there are plenty of remote work-friendly vacation rentals available, with around 59 options to choose from. This charming waterfront area provides a picturesque backdrop for those looking to combine work and leisure. Many of these rentals come equipped with essential amenities for remote work, such as free Wi-Fi, dedicated desks, and comfortable desk chairs, ensuring that travelers can stay productive during their stay.

The neighborhood is known for its vibrant maritime culture, with easy access to local attractions like the Eastport Yacht Club and various waterfront parks. Additionally, the proximity to downtown Annapolis allows for a blend of relaxation and exploration, with restaurants, shops, and historical sites just a short distance away. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Eastport vacation rental?
Book your Eastport vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Eastport, Maryland, United States of America?
In Eastport, Maryland, visitors can enjoy a blend of maritime charm and vibrant local culture. One of the top attractions is the historic Eastport neighborhood itself, known for its picturesque waterfront views and small-town feel. The area boasts a variety of shops, galleries, and seafood restaurants, making it a great place to explore on foot.

The nearby Annapolis City Dock is also a must-visit, where travelers can watch boats come and go while enjoying local dining options and outdoor entertainment. The United States Naval Academy, located just across the water, offers guided tours that provide insight into its rich history and stunning architecture.

For those interested in the arts, the Eastport Arts District hosts numerous galleries and art events throughout the year, showcasing local talent.
Can I change or cancel my Eastport home rental booking on Vrbo?
To find Eastport vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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.

More Vacation Ideas