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  2. Maryland
  3. Annapolis
  4. Eastport
  5. Rentals by Owner

Eastport Rentals by Owner

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10.0 (1 Review)
House
  • Air Conditioner
  • Balcony/Terrace
  • Security/Safety
9.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool
New
House
  • Parking
  • Barbecue/Outdoor Cooking
  • Child Friendly

Why Choose Rent By Owner for your Eastport vacation rental?

What makes our Rentals by Owner 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 Rentals by Owner stay?

Choosing the optimal time to vacation here can enhance your experience, as the area offers different charms and activities depending on the season, making it essential to plan your trip accordingly for a seamless and memorable stay.

Peak Season Highlights

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Summer (June to August)

During the summer months, you'll experience warm temperatures ideal for enjoying the region's outdoor activities and scenic views.

Average Temperature Daytime: around 85°F (29°C) - Nighttime: about 70°F (21°C)
autumn
Fall (September to November)

This season offers pleasant weather and vibrant scenery, making it a perfect time for exploring local attractions and enjoying outdoor pursuits.

Average Temperature Daytime: roughly 75°F (24°C) - Nighttime: around 55°F (13°C)

Off-Season Highlights

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Winter (December to February)

The winter months bring cooler temperatures and fewer tourists, which can provide a quieter and more relaxed stay here.

Average Temperature Daytime: approximately 45°F (7°C) - Nighttime: near 30°F (-1°C)
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Early Spring (March to April)

As the region transitions into spring, you may find fewer crowds and lower rates, ideal for those seeking a peaceful retreat.

Average Temperature Daytime: around 55°F (13°C) - Nighttime: about 40°F (4°C)

Weekly Weather Forecast for Eastport

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.

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 options on a spacious patio or deck, perfect for entertaining amid scenic views.
  • Take advantage of a private yard or garden area to relax and unwind in the fresh air.
  • Make the most of a waterfront setting with access to a dock or pier for boating and fishing activities.
  • Relax by an outdoor fireplace or fire pit, ideal for cozy evenings under the stars.
  • Utilize a barbecue grill for preparing meals outside during your stay here.
  • Benefit from shaded areas such as canopy-covered patios or pergolas to stay cool outdoors.
  • Experience outdoor recreational amenities like a pool or hot tub for added leisure during your visit.
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Family Activities

  • Annapolis Maritime Museum & Park: Discover maritime history and enjoy hands-on exhibits that are perfect for engaging young minds and families alike.
  • Eastport Yacht Centre: Observe sailing vessels and participate in family-friendly boat tours that highlight the region’s rich nautical culture.
  • Quiet Waters Park: Relax in this scenic park offering walking trails, playgrounds, and outdoor spaces ideal for a family picnic or an afternoon of exploration.
  • Downtown Annapolis Historic District: Stroll through charming streets filled with shops, galleries, and historic landmarks that captivate visitors of all ages.
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Adult Activities

  • Marina Tours and Sailing Experiences: Explore the scenic Chesapeake Bay with guided boat tours or sailing excursions that showcase the area's natural beauty and maritime heritage.
  • Indulge in waterfront dining options that highlight fresh seafood and regional flavors, offering a taste of the region’s culinary delights.
  • Historical Walking Tours: Discover the rich history and charming streets through guided walks that provide insight into the area's nautical past and local landmarks.
  • Kayaking and Paddleboarding Adventures: Enjoy the tranquil waters by renting equipment for paddling along the shoreline, perfect for both beginners and experienced water enthusiasts.

Other Places to Stay in Eastport, MD

Annapolis Maritime Museum

Eastport Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local waterfront dining: Take advantage of the area's scenic views by dining at the region’s waterfront restaurants, offering authentic Annapolis flavors during your stay.
  • Visit nearby marinas and boat rentals: Enhance your trip by renting a boat or simply enjoying the marina views, allowing you to experience the region’s maritime charm firsthand.
  • Plan outdoor activities in parks and natural areas: Make the most of your visit by exploring the region’s parks and outdoor spaces, perfect for relaxing and appreciating the local scenery.
  • Utilize local guided tours and experiences: Discover hidden gems and gain insider knowledge by booking guided tours that highlight the best of this destination's history and culture.

Transportation Options

  • Water Taxi: Enjoy scenic transportation across the harbor, offering a convenient way to explore nearby attractions from your rental in the area.
  • Local Bus Services: Utilize the regional bus network for affordable and reliable travel within Annapolis and the surrounding neighborhoods, making it easy to reach key points of interest.
  • Taxi and Rideshare Services: Access on-demand taxis and rideshare options directly from your rental, providing flexible transportation throughout the region.
  • Car Rentals: Rent a vehicle locally to comfortably explore beyond the immediate area, with numerous providers catering to visitors seeking independence during their stay.

Local Customs Options

  • Maritime Traditions: Locals here take pride in their longstanding maritime heritage, often showcasing it through community events and local crafts.
  • Cocktail Culture: Enjoy the region’s unique take on waterfront hospitality, where socializing over drinks like the traditional Maryland crab cocktail is customary.
  • Respect for Local History: Visitors are encouraged to honor the area's rich past by participating in guided tours and respecting preservation efforts.
  • Community Gatherings: Regular events and festivals emphasize a close-knit spirit and shared appreciation for the region's cultural roots.

Eastport Rentals by Owner Frequently Asked Questions

1. What is the cancellation policy for a rental by owner in this area?

The cancellation policy varies depending on the individual listing. You should review the specific terms listed on the property page or contact the owner directly to understand the cancellation conditions and any applicable fees.

2. How do I communicate with the property owner before booking?

You can reach out to the owner through the messaging platform provided on the booking site. This allows you to ask questions, clarify details, and ensure the rental meets your needs before confirming your reservation.

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

Additional fees such as cleaning, service charges, or local taxes may apply and are typically detailed in the listing. Always review the total price breakdown before finalizing your booking to avoid surprises.

4. What amenities are usually included in a rental by owner in this region?

Most rentals by owner in this destination include essential amenities like Wi-Fi, kitchen facilities, parking, and linens. Specific offerings are listed on each property page, so it’s best to check them directly for exact details.

5. Is there a minimum stay requirement for booking a rental here?

Minimum stay requirements vary by property. These details are specified on the listing, and if you have special requests, contacting the owner can help clarify flexibility regarding booking durations.

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