Annapolis Rentals by Owner
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Pet Friendly
- Security/Safety
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- TV
Why Choose Rent By Owner for your Annapolis vacation rental?
What makes our Rentals by Owner special?
Popular Areas for Annapolis Rentals by Owner
Where are the best neighborhoods to stay in Annapolis?
When exploring your options for a memorable stay, choosing the right neighborhood in Annapolis, Maryland can greatly enhance your experience. The city offers charming districts that blend historic charm with modern comfort, making it easy to find a rental by owner through Rent By Owner that suits your preferences. Whether you prefer staying near the bustling waterfront, the peaceful residential areas, or the vibrant downtown scene, each neighborhood provides unique amenities and easy access to local attractions. By selecting the ideal neighborhood in Annapolis, you ensure a seamless and enjoyable visit tailored to your interests.
Historic District
Stay within this charming area to immerse yourself in the city’s rich history and walk among beautifully preserved architecture, making it an ideal choice for travelers seeking a blend of culture and convenience.
View 506+ Rentals in Historic DistrictArundel on the Bay
This tranquil neighborhood offers scenic waterfront views and peaceful surroundings, providing the perfect setting for a relaxing escape and easy access to regional attractions.
View 155+ Rentals in Arundel on the BayEastport
Known for its vibrant maritime charm, the area features quaint streets and waterfront activities, making it a favorite for those looking to enjoy the region’s nautical heritage.
View 71+ Rentals in EastportWest Annapolis
Experience the warmth of this community that offers a mix of historic buildings and local eateries, perfect for travelers who want to explore the region's local flavor.
View 710+ Rentals in West AnnapolisOyster Harbor
Set along scenic waterways, this neighborhood provides serene vistas and access to outdoor recreational activities, making it ideal for nature lovers visiting here.
View 220+ Rentals in Oyster HarborMurray Hill
A quiet residential enclave, Murray Hill offers a peaceful environment close to downtown, suitable for visitors seeking comfortable stays with easy access to the area's highlights.
View 26+ Rentals in Murray HillHomewood
Nestled in a scenic part of town, Homewood combines residential charm with proximity to key attractions, making it an excellent choice for relaxed yet convenient lodging.
View 722+ Rentals in HomewoodHunt Meadows
This friendly neighborhood offers spacious accommodations and easy access to the region’s important sites, ideal for travelers seeking comfort and accessibility during their visit.
View 776+ Rentals in Hunt MeadowsBest Times to Visit Annapolis
When should you plan your Rentals by Owner stay?
Choosing the optimal time to vacation in Annapolis can enhance your experience, allowing you to enjoy this destination’s unique charm and local events while ensuring your rental by owner through Rent By Owner aligns perfectly with your travel plans.
Peak Season Highlights
Spring (March to May)
During this time, the region comes alive with pleasant weather and vibrant scenery, making it ideal for exploring local attractions and enjoying outdoor activities from your rental by owner.
Summer (June to August)
Summertime offers warm temperatures and long daylight hours, perfect for leisurely strolls around the area and making the most of your stay at a vacation rental here.
Off-Season Highlights
Fall (September to November)
As the leaves change color, this season provides cooler temperatures and fewer crowds, giving you a peaceful experience while staying at a rental by owner in this destination.
Winter (December to February)
The winter months bring colder weather, making it an ideal time for those seeking a quiet retreat in a cozy rental while enjoying the tranquility of the region.
Weekly Weather Forecast for Annapolis
How to Book Your Annapolis vacation rental
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Annapolis
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 relaxing evenings around your private outdoor seating area or patio, perfect for unwinding after exploring the area.
- Take advantage of lush gardens or landscaped yards that provide a peaceful outdoor retreat during your stay.
- Make use of outdoor grilling stations or BBQ areas to host memorable cookouts with friends or family.
- Benefit from scenic views and spacious decks that allow you to soak in the natural beauty of this region.
- Utilize outdoor dining spaces ideal for alfresco meals while enjoying the pleasant climate of the local area.
- Explore well-maintained walkways, paths, or garden trails that offer delightful ways to enjoy the outdoors right at your rental.
- Relax in a private pool or hot tub if available, providing a luxurious outdoor experience during your visit here.
Top Attractions Around Annapolis
What attractions are nearby?
In this charming destination, you can enjoy a variety of nearby activities such as exploring historic sites, sailing on scenic waters, or strolling through vibrant neighborhoods, making it an ideal spot for memorable getaways booked through Rent By Owner.
Family Activities
- U.S. Naval Academy Tour: Explore the historic grounds and learn about naval history, providing an educational experience perfect for families interested in American maritime heritage.
- Annapolis Maritime Museum & Park: Discover interactive exhibits and enjoy waterfront views that introduce children to the region’s rich shipping and boat-building traditions.
- Sailing Adventures on the Chesapeake Bay: Embark on family-friendly sailing excursions that offer a fun way to experience the area’s renowned waterways firsthand.
- Main Street Annapolis Exploration: Stroll through charming boutiques and cafes, allowing your family to soak up local culture and enjoy picturesque scenery at your own pace.
Adult Activities
- Historical Harbor Tours: Explore the area's rich maritime history by taking a harbor cruise that offers stunning views of the waterfront and insights into local navigation traditions.
- Wine and Spirit Tastings: Visit renowned wineries and distilleries in this destination to indulge in tastings that showcase regional flavors and craftsmanship.
- Dining Experiences at Waterfront Restaurants: Enjoy a variety of seafood and local cuisine with scenic views of the water, perfect for relaxing evenings after a day of exploration.
- Art Galleries and Cultural Centers: Discover the vibrant arts scene at various galleries and cultural institutions, where you can appreciate the region’s creative talents.
Other Places to Stay in Annapolis, MD
Annapolis Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Eateries: Take advantage of the region’s culinary scene by trying local restaurants and fresh seafood to get a true taste of the area's unique flavors.
- Plan Scenic Waterway Tours: Make the most of your stay by booking boat or kayak rentals to enjoy the region’s picturesque waterways and scenic views.
- Visit Historic Districts: Allocate time to wander through the charming historic neighborhoods to immerse yourself in the area's rich maritime heritage and architecture.
- Book Rentals Close to Attractions: Choose accommodations near key attractions or waterfront areas for easy access and more enjoyable sightseeing experiences.
Transportation Options
- Car Rentals: Renting a car provides flexible and convenient transportation to explore the area's scenic spots and local attractions at your own pace.
- Public Transit: The regional bus services offer an affordable way to navigate here and reach key destinations within the city and surrounding neighborhoods.
- Taxi and Rideshare Services: Taxis and rideshare options like Uber and Lyft provide quick, reliable transportation around this lively destination.
- Biking and Walking: Biking and walking are popular choices for experiencing the charming streets and waterfront scenery at a relaxed pace in this area.
Local Customs Options
- Respect for Maritime Traditions: Engaging with the area’s rich maritime history means observing local customs such as maritime festivals and boat parades that highlight this destination's seaside heritage.
- Celebration of Historic Heritage: Appreciating the region’s Colonial-era architecture and participating in guided tours or events helps you connect with the area's preserved historical significance.
- Supporting Local Artisans: When exploring here, it's common to buy handmade crafts and artwork from local vendors, reflecting the community’s dedication to its creative spirit.
- Embracing Waterfront Dining Etiquette: Enjoying meals at waterfront restaurants involves a relaxed yet courteous approach, aligning with the region’s laid-back coastal vibe.
Annapolis Rentals by Owner Frequently Asked Questions
1. What is the cancellation policy for a rental by owner in Annapolis, Maryland?
2. How do I book a rental property in Annapolis through Rent By Owner?
3. Are there any additional fees I should be aware of when booking a rental in Annapolis?
4. What amenities are usually included with vacation rentals by owner in the area?
5. How can I communicate with the owner before confirming my stay in Annapolis?
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