Eastport vacation rentals

We found 182 vacation rentals — enter your dates for availability

Discover a selection of 36 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:Nov 21 - Nov 28
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Find out more about Eastport

Find out more about Eastport

Why visit Eastport

  1. Scenic waterfront views: Enjoy picturesque panoramas along Eastport's charming shoreline, perfect for relaxation and photography.
  2. Outdoor dining: Indulge in delicious meals at local cafes while soaking up the vibrant atmosphere of the neighbourhood.
  3. Rich history: Immerse yourself in Eastport's heritage by exploring historic houses and cultural landmarks.
  4. Family-friendly activities: Engage in various outdoor adventures suitable for all ages, ensuring a fun-filled experience for everyone.
  5. Diverse accommodation options: Choose from cozy cottages, modern apartments, or charming vacation homes to enhance your stay.

Popular types of accommodation around Eastport

If you're considering a getaway to Eastport, you're in for a treat! The most popular types of vacation rentals here include charming houses, cozy cottages, and modern apartments. Whether you're seeking waterfront rentals or friendly accommodations, Eastport has something for everyone. Explore the diverse options available and enjoy a memorable stay in this picturesque destination, where transparency and savings meet reassurance for your travel experience.

  • Houses: The top choice for holidaymakers in Eastport, offering a spacious and comfortable stay for families, couples, or groups.
  • Cottages: A charming option for those seeking a quaint and cozy retreat, perfect for enjoying the local scenery.
  • Apartments: A practical selection for visitors wanting a self-contained space, ideal for urban living.
  • Condos: A modern lodging choice that combines style and convenience, often featuring shared amenities.
  • Villas: Luxurious accommodations providing ample space and upscale features for a lavish getaway.**

Top attractions around Eastport

Eastport, Annapolis, Maryland, is an ideal family-friendly destination for outdoor enthusiasts and city explorers alike. Visitors can enjoy various attractions such as urban parks, historic houses, and national state parks, all of which offer rich cultural experiences. Additionally, beach access in Eastport provides a perfect spot for relaxation and recreation. Whether you're travelling solo or with family, Eastport has something for everyone to enjoy.

  1. U.S. Naval Academy: Immerse yourself in history and maritime culture at this prestigious institution. Explore stunning architecture, beautiful grounds, and fascinating exhibits that celebrate naval heritage.
  2. Chesapeake Bay Bridge: Experience breathtaking views from this modern marvel that connects the Eastern and Western shores. Its impressive structure offers a unique perspective of the Chesapeake Bay.
  3. Maryland State House: Discover the rich political history of Maryland in this historic building. With its stunning architecture and vibrant artwork, it reflects the state’s cultural heritage.

Things to do recommended for couples

For a romantic getaway in Eastport, enjoy a sailing adventure at Annapolis Sailing School, only 644m away. Experience the grace of the Ballet Theater of Maryland, a mile from Eastport, or indulge in fine wines at St. Michaels Winery, 30.6km away, for a perfect couples’ day.

Things to do recommended for families

Your family will love visiting the Navy-Marine Corps Memorial Stadium for some sports excitement, enjoying arcade fun at Annapolis Bowl, and relaxing in nature at Fort Smallwood Park. These activities offer a fantastic blend of adventure, sport, and wellness, perfect for creating lasting memories together.

Things to do recommended for groups

Explore the Annapolis Mall Shopping Center for a fun shopping experience, enjoy a night out at Maryland Live Casino, or hit the greens at the nearby Annapolis Golf Club for some outdoor sports. Each location offers a unique vibe perfect for group travelers!

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

If you're planning a trip with a group, family, pets, or are interested in extended stays, it's important to prioritize your preferences when filtering options. Here are some helpful Vrbo booking tips for you.

  • Traveling to Eastport with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Eastport with young kids: Travelling with young children 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, a family getaway wouldn’t be the same without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Eastport: If you're in search of vacation rentals offering great deals for stays of a month or more, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly accommodations. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay around Eastport

Eastport, a charming neighbourhood in Annapolis, offers a delightful blend of outdoor adventures and family-friendly activities. Explore its scenic waterfront views, indulge in outdoor dining at local cafes, and immerse yourself in the area's rich history. Nearby attractions enhance your experience, making it ideal for both relaxation and excursions. Whether you're strolling through picturesque streets or enjoying the oceanfront, Eastport promises an unforgettable getaway full of warmth and friendly faces.

  • Historic District: The Historic District is a charming neighbourhood located 1.4km from Eastport. This area is rich in history and offers a delightful blend of family-friendly activities and outdoor experiences. Visitors can explore the vibrant shopping area, which features unique boutiques and local shops. The proximity to local landmarks, such as the academy and the bustling dock port, makes it a perfect spot for education and leisure. With its picturesque streets and historic architecture, the Historic District invites you to stroll leisurely and soak in the local culture.
  • Naval Academy: Situated 1.6km from Eastport, the Naval Academy is a unique village that provides a captivating insight into maritime culture. This area is great for families and offers a variety of outdoor experiences. The local shopping area and recreational facilities ensure that there is something for everyone. Key attractions include the prestigious academy itself and the adjacent tourist precinct, where you can delve into the naval history and enjoy scenic views of the dock port. A visit here is both educational and entertaining, making it a must-see.
  • Murray Hill: Located 1.6km from Eastport, Murray Hill is a picturesque neighbourhood perfect for those seeking outdoor activities and family-friendly experiences. With its scenic parks and recreational areas, this community encourages visitors to engage in outdoor pursuits. The local shopping area offers a variety of options for dining and leisure. Nearby attractions include the academy and a beautiful beach, providing ample opportunities for relaxation and exploration. Murray Hill’s inviting atmosphere makes it an ideal spot to unwind and enjoy the local charm.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 HighSlightly High
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 SunnyAverageAverage
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 adventure? Consider being flexible with your travel dates, as prices can fluctuate significantly. Moreover, extending your stay can often result in fantastic savings. To discover the ideal Vrbo property that fits your budget, use our filters to refine your search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly platform for planning your travels, allowing you to start new trips, resume previous ones, or manage your itinerary with ease. Here, you can effortlessly find your saved or booked properties organized into categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-ca/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 common type of rental, with about 30 available throughout the area. These properties often feature spacious interiors, multiple bedrooms, fully equipped kitchens, and outdoor spaces for enjoying the pleasant Maryland weather. Many houses are situated close to the waterfront, providing easy access to local attractions and the vibrant atmosphere of Eastport's historic streets.
Are there any beach house rentals in Eastport?
In Eastport, Maryland, several beach house rentals are available, primarily located near the scenic waterfront and charming local marinas. These properties often come with amenities such as spacious living areas, fully equipped kitchens, and outdoor decks or patios that provide stunning views of the bay. Many beach houses are designed to accommodate families or groups, featuring multiple bedrooms and bathrooms, making them great for a relaxing getaway.
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 travelling 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.
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.
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 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 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. 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 vacation rental?
July is the most popular month to visit Eastport, making it an ideal time for vacation rentals. This period falls within the peak season, which runs from May to July, and offers visitors the chance to immerse themselves in vibrant summer activities. The charming waterfront community comes alive with boating, fishing, and delightful outdoor dining, all set against the backdrop of pleasant temperatures averaging around 27°C.

During this bustling season, you can enjoy the warm weather while exploring the beautiful waterfront and indulging in the local seafood cuisine. The lively atmosphere is superb for those who relish socializings and wish to connect with fellow holidaymakers. The nearby Chesapeake Bay offers a wealth of opportunities for kayaking and sailing, making it an adventure-lover's playground.

For those who prefer a quieter experience, consider planning your visit in December. While this month may be less crowded, it provides a unique opportunity to enjoy Eastport's festive charm as the community decorates for the vacation season. Strolling through the quaint streets lined with twinkling lights can be a magical experience, and you might even catch local vacation events.
Are there any remote work vacation rentals in Eastport?
In Eastport, Maryland, there are numerous remote work vacation rentals available, with around 42 options to choose from. This charming waterfront community offers a delightful blend of relaxation and productivity, making it an ideal place for those seeking to balance work and leisure. Many of the properties are well-equipped with essential amenities such as Wi-Fi, dedicated office spaces, desks, and desk chairs, ensuring that guests can comfortably work from home while enjoying the picturesque surroundings. 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?
Eastport, Maryland, offers a charming waterfront atmosphere with several great attractions. Visitors can explore the historic district, which features quaint streets lined with colourful houses and local boutiques. The Eastport Yacht Club is a focal point for sailing and boating enthusiasts, and the nearby Annapolis Maritime Museum provides insights into the region's maritime heritage. For those looking to enjoy the outdoors, the scenic waterfront parks along the Chesapeake Bay offer picturesque views and walking trails.
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 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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

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