Discover Your Perfect Eastport Vacation Homes

Eastport Luxury Rentals

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Lighthouse Inn
  • Parking
  • Barbecue/Outdoor Cooking
  • Child Friendly
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Eastport Pet Friendly Vacation Rentals

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Eastport Large Vacation Homes

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Why Choose Rent By Owner for your Eastport Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Eastport

When should you plan your Vacation Rentals stay?

Choosing the best time to visit here ensures you can fully enjoy all that this charming region has to offer, whether you're seeking vibrant local events or peaceful scenic moments in Eastport, Annapolis.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

This is the most popular time to visit, as the weather in the area becomes warm and welcoming, ideal for enjoying outdoor activities and the scenic views around Annapolis. Expect higher demand for vacation rentals during this period.

Average Temperature Daytime: 75°F - Nighttime: 60°F
autumn
Early Fall (September to October)

During these months, the region experiences comfortable temperatures and vibrant surroundings, attracting visitors seeking to enjoy the area's maritime charm before the winter arrives. Booking early is recommended for the best vacation rentals here.

Average Temperature Daytime: 70°F - Nighttime: 55°F

Off-Season Highlights

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Winter (December to February)

The quietest time of year, when fewer travelers visit, making it an ideal period for those seeking a peaceful retreat in the region. Vacation rentals are more accessible and often more affordable during this season.

Average Temperature Daytime: 45°F - Nighttime: 30°F
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Early Spring (March to April)

As the area transitions into warmer weather, visitor numbers decrease, offering a serene environment to explore local sights at a leisurely pace. It’s a great time for booking vacation rentals with flexible availability.

Average Temperature Daytime: 55°F - Nighttime: 40°F

Weekly Weather Forecast for Eastport

How to Book Your Eastport Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Eastport

More Top-Rated Vacation Rentals in Eastport Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy outdoor dining areas with scenic views of the surrounding waterways.
  • Relax on private patios or decks equipped with comfortable seating options.
  • Make the most of lush gardens or landscaped yards that add to your outdoor experience.
  • Take advantage of direct access to nearby docks or piers for boating and fishing adventures.
  • Benefit from outdoor grills or BBQ facilities perfect for gatherings with family and friends.
  • Experience serene waterfront settings with private balconies overlooking the harbor.
  • Utilize outdoor showers or changing areas that enhance your coastal retreat experience.

Top Attractions Around Eastport

What attractions are nearby?

Within this charming region, you can enjoy a variety of outdoor activities, explore scenic waterfronts, and immerse yourself in local culture—all just moments from your Eastport vacation rental in Annapolis, Maryland.

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Family Activities

  • Visit the Chesapeake Bay Maritime Museum: Explore this engaging museum to learn about the area's rich maritime history through interactive exhibits and authentic boat displays.
  • Enjoy a family-friendly harbor cruise: Take a scenic boat tour around the region’s picturesque waters, offering spectacular views and educational opportunities for all ages.
  • Discover local parks and outdoor spaces: Spend quality time outdoors at nearby parks that provide playgrounds, walking trails, and waterfront picnic areas perfect for family outings.
  • Attend community events and festivals: Experience the vibrant local culture by participating in seasonal events and festivals held throughout the year here, suitable for family fun and memorable moments.
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Adult Activities

  • Sailing Tours: Experience the maritime charm of this destination by taking a sailing tour around the Chesapeake Bay, offering unforgettable views and a relaxing voyage.
  • Enjoy an evening cocktail cruise, where you can unwind with signature drinks while taking in the scenic waterfront vistas of the region.
  • Marina Activities: Spend time at local marinas engaging in boating, paddleboarding, or simply strolling along the docks to embrace the area's nautical ambiance.
  • Historical Harbor Walks: Discover the rich maritime history through guided or self-guided walks along the harbor, gaining insight into the area's legacy and culture.

Other Places to Stay in Eastport, MD

Annapolis Maritime Museum
Annapolis Maritime Museum Vacation Rentals
More Places to Stay Near Eastport

Eastport Travel Tips

How Can You Make the Most of Your Stay?

  • Explore the Waterfront: Take advantage of your stay by enjoying the scenic waterfront views and leisurely activities that showcase the area's maritime charm.
  • Visit Local Eateries: Indulge in the region’s fresh seafood and regional cuisine at nearby restaurants to get a true taste of the destination.
  • Plan Outdoor Adventures: Make the most of the pleasant climate with outdoor excursions such as kayaking, sailing, or walking along scenic trails.
  • Discover Unique Shops: Spend time exploring boutique stores and art galleries that reflect the character and culture of this vibrant destination.

Transportation Options

  • Drive or Rent a Car: You can explore the area comfortably by renting a vehicle, offering flexibility to visit nearby attractions and enjoy scenic drives around Annapolis.
  • Public Transit: The local bus services provide an affordable and convenient way to navigate this destination without the hassle of parking.
  • Taxis and Ride-Sharing Services: Taxis and popular ride-sharing options are readily available for quick, door-to-door transportation throughout this part of Maryland.
  • Biking and Walking: For shorter distances, you can enjoy the region’s bike paths and walkable streets, immersing yourself in the local charm of the area.

Local Customs Options

  • Clam Bake Traditions: Participating in local clam bake events reflects the area's maritime heritage and is a cherished custom here.
  • Pirate Heritage Celebrations: Engaging in lively festivities that honor the region's historical connection to pirates offers an authentic cultural experience.
  • Seafood Festivals: Attending seasonal seafood festivals highlights the community’s love for fresh Maryland blue crabs and other regional delicacies.
  • Boating Etiquette: Practicing respectful boating customs on the water showcases the area's rich nautical traditions and promotes harmony among boaters.

Frequently Asked Questions About Eastport?

1. What are the top vacation rentals in Eastport?

There are a lot of options in Eastport. If you plan on staying in the Eastport area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Eastport:

2. How many vacation rentals have private pools in Eastport?

There are 1 vacation rentals with private pools near Eastport. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Eastport are best for families?

If you are looking for a family-friendly vacation home in Eastport, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Eastport:

4. How many Rentbyowner vacation rentals are available in Eastport?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 98 in the Eastport area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Eastport. 

5. What is the cancellation policy for booking vacation rentals in Eastport, Annapolis?

The cancellation policy varies depending on the specific property. You should review the detailed policy listed with each rental or contact the owner directly to understand any fees or restrictions.

6. Are there any additional fees I should be aware of when booking a vacation rental here?

Additional fees such as cleaning, service charges, or local taxes are typically outlined in the listing details. It's advisable to read the full description and contact the host if you have questions about extra costs.

7. How do I ensure my reservation is secure and confirmed for this destination?

Reservations are generally confirmed through the booking platform once your payment is processed. For added peace of mind, verify the host’s reviews and policies before completing your booking.

8. What amenities are usually included with vacation rentals in the area?

Popular amenities often include Wi-Fi, parking, kitchen facilities, and outdoor spaces. Specific amenities vary by property, so check each listing carefully to match your needs.

9. Is there a minimum stay requirement for vacation rentals in this region?

Minimum stay requirements depend on the property owner’s policies and may differ from one rental to another. Details are typically provided on the listing page or can be confirmed by contacting the owner.