Discover Your Ideal Eastport, Annapolis Rental by Owner for a Memorable Stay
Discover Your Perfect Eastport Rentals by Owner
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Rentals by Owner
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Sustainable Travel
Eastport Rentals by Owner
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Balcony/Terrace
- Security/Safety
- 1754 ft² House
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- 2699 ft² House
- Air Conditioner
- Parking
- TV
- Air Conditioner
- TV
- Security/Safety
- Parking
- Barbecue/Outdoor Cooking
- Child Friendly
- 2701 ft² House
- Air Conditioner
- TV
- Transportation/Shuttle
- Air Conditioner
- Parking
- TV
- Parking
- Barbecue/Outdoor Cooking
- Child Friendly
- Air Conditioner
- Pet Friendly
- TV
Why Choose Rent By Owner for your Eastport vacation rental?
What makes our Rentals by Owner special?
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
Summer (June to August)
During the summer months, you'll experience warm temperatures ideal for enjoying the region's outdoor activities and scenic views.
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.
Off-Season Highlights
Winter (December to February)
The winter months bring cooler temperatures and fewer tourists, which can provide a quieter and more relaxed stay here.
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.
Weekly Weather Forecast for Eastport
How to Book Your Eastport vacation rental
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Eastport
Common Rentals by Owner Amenities
What amenities can you expect?
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.
Top Attractions Around Eastport
What attractions are nearby?
Enjoy a variety of nearby activities in the region, from exploring local maritime attractions to relaxing along scenic waterfronts, all easily accessible when you choose your rental here in Eastport, Annapolis.

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.
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
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?
2. How do I communicate with the property owner before booking?
3. Are there any additional fees I should be aware of when booking a rental here?
4. What amenities are usually included in a rental by owner in this region?
5. Is there a minimum stay requirement for booking a rental here?
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