Eastport vacation rentals

We found 181 vacation rentals — enter your dates for availability

Discover a selection of 54 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.

Vacation rentals with weekly discounts - Eastport

Showing deals for:Apr 17 - Apr 24

Image gallery for Secluded Cozy Cottage in Historic Downtown

Living area
9.6 out of 10, Exceptional, (16 reviews)
Exceptional
(16 reviews)

Secluded Cozy Cottage in Historic Downtown

Annapolis

18% off
Price is $406
$2,845 for 7 nights
All fees included
Secluded Cozy Cottage in Historic Downtown

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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.

Unlock savings with One Key

When you reserve an eligible Vrbo for your group getaway, you'll earn OneKeyCash on the full booking amount. Being the organizer truly has its benefits. Enroll in our One Key rewards program to unlock exclusive savings for members and accumulate OneKeyCash on qualifying stays. Sign up today and start enjoying the rewards.

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 around 30 available throughout the charming neighborhood. These houses typically feature multiple bedrooms, spacious living areas, and often include outdoor spaces like patios or decks, making them ideal for families or groups looking to enjoy the coastal atmosphere. Additionally, there are several condos and apartments, which provide a more compact option for travelers seeking convenience and proximity to local attractions. Houseboats and cottages are also available, offering unique stays that let visitors experience the area's maritime charm.
Are there any beach house rentals in Eastport?
In Eastport, Maryland, there are approximately 77 beach house vacation rentals available, primarily located close to the picturesque waterfront and within walking distance of the charming historic district. These rentals typically feature spacious layouts, multiple bedrooms, and amenities such as fully equipped kitchens, outdoor decks, and sometimes direct access to the shoreline. Many properties also provide stunning views of the Chesapeake Bay, making them ideal for families or groups looking to enjoy the local scenery and coastal activities.
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, which allow travelers to prepare their own meals. Many rentals also feature blenders and coffee/tea makers, suiting those who enjoy homemade beverages. Outdoor spaces are common, with decks or patios available for relaxing and enjoying the pleasant surroundings.
Are there any family house rentals in Eastport?
In Eastport, Maryland, there are around 30 family-friendly house rentals available, making it a wonderful choice for those traveling with children. This charming area, with its proximity to the scenic Chesapeake Bay, features various homes that cater to families. Many of these properties come with spacious living rooms, fully equipped kitchens for preparing family meals, and outdoor spaces where kids can enjoy the fresh air and play.

Visitors can explore nearby attractions such as the Annapolis Maritime Museum and the picturesque waterfront, which is superb for leisurely strolls or picnics. Additionally, families can take advantage of local parks that offer playgrounds and recreational activities.
Can I rent a vacation home with a pool or hot tub in Eastport?
In Eastport, Maryland, travelers can find several vacation homes available for rent that feature both pools and hot tubs. This charming waterfront community offers a picturesque setting, with many properties located near the scenic Annapolis Harbor. Visitors can expect amenities such as private swimming pools, relaxing hot tubs, spacious outdoor decks, and fully equipped kitchens, making these rentals ideal for families or groups looking to enjoy a comfortable getaway.
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.
Are there pet-friendly vacation rentals in Eastport?
In Eastport, Maryland, travelers can easily find pet-friendly vacation rentals, with approximately 15 options available. This charming waterfront community offers a variety of accommodations, including cozy cottages and spacious homes that often come equipped with modern amenities such as full kitchens, outdoor spaces, and comfortable living areas. Many properties have features like fenced yards or nearby parks, making them ideal for guests traveling with pets.

The Eastport area is known for its picturesque views of the Annapolis Harbor and proximity to several parks, including the scenic Eastport Park, which provides lovely walking trails and open spaces great for pet owners. Additionally, the vibrant local dining scene includes several pet-friendly restaurants with outdoor seating, allowing travelers to enjoy meals while accompanied by their furry friends.
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 visit Eastport for a vacation rental is during the peak season from May to July, when the vibrant coastal town comes alive with activity. With July being the most popular month, travelers can indulge in an array of outdoor experiences, such as sailing, kayaking, and enjoying the local seafood at waterfront restaurants. The warm weather, with temperatures typically ranging from the mid-70s to low 90s Fahrenheit, makes for ideal conditions for exploring the charming streets and scenic waterfront.

As the summer months are bustling with tourists, you'll find plenty of opportunities for socializing and enjoying community events. The lively atmosphere during this time is great for those who thrive on adventure and interaction with fellow travelers.

For those looking for a more budget-friendly experience, consider visiting Eastport in December. While temperatures drop to the low 30s to mid-40s Fahrenheit, this quieter time of year offers a unique charm with fewer crowds and the chance to experience the local holiday festivities.
Are there any remote work vacation rentals in Eastport?
In Eastport, Maryland, there is a substantial selection of remote work vacation rentals available, with around 41 options to choose from. This charming waterfront community, located just across the bridge from Annapolis, combines the beauty of the Chesapeake Bay with a vibrant local atmosphere. Many of the rentals here are equipped with essential remote work amenities such as high-speed Wi-Fi, dedicated desks, and comfortable office chairs, making it easy for travelers to maintain productivity while enjoying a coastal getaway.

Eastport itself offers a delightful blend of quaint streets lined with historic homes and picturesque marinas. Visitors can explore local points of interest, including the scenic Eastport Yacht Club and various waterfront parks. Additionally, the area's proximity to downtown Annapolis means that guests can easily access a wide array of restaurants, shops, and cultural attractions, enhancing their overall experience. 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?
In Eastport, Maryland, visitors can enjoy a variety of attractions that highlight the area's maritime charm. The Eastport neighborhood itself is known for its picturesque waterfront views and vibrant boating community. One of the main highlights is the scenic Eastport Yacht Club, where sailing and other water sports are popular.

Just a short walk away, visitors can explore the historic district, which features quaint shops and restaurants offering fresh seafood and local cuisine. The nearby Annapolis City Dock is a hub for tourists, showcasing a lively atmosphere with outdoor events and beautiful views of the Chesapeake Bay.

For those interested in history, the Banneker-Douglass Museum provides insights into African American heritage in Maryland. The area is also close to the U.S. Naval Academy, where guided tours allow visitors to learn about its storied past.
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.

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