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Annapolis Luxury Rentals

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Annapolis Pet Friendly Vacation Rentals

7.2 (329 Reviews)
Hotel
Red Roof Inn Annapolis
  • Air Conditioner
  • Parking
  • Pet Friendly
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Annapolis Large Vacation Homes

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Why Choose Rent By Owner for your Annapolis 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.

Popular Areas for Annapolis Vacation Rentals

Where are the best neighborhoods to stay in Annapolis?

When selecting a neighborhood to stay in Annapolis, Maryland, you'll find that each area offers its own unique charm and convenience. Whether you prefer the historic streets of downtown Annapolis with their vibrant local scene or the peaceful residential neighborhoods with scenic views, there is a perfect spot for your getaway. Staying in the right neighborhood can enhance your experience, offering easy access to the city's renowned sights and authentic local culture. Explore the diverse options available to find the ideal location that suits your preferences and makes your visit to Annapolis memorable.

Historic District

Stay in the heart of the region’s most iconic area, where charming streets and historic architecture create an inviting atmosphere for exploring Annapolis. This neighborhood offers easy access to local landmarks and a glimpse into the area's rich history.

View 506+ Rentals in Historic District

Arundel on the Bay

Enjoy waterfront views and a tranquil ambiance in this peaceful neighborhood, perfect for relaxing by the water. It provides a serene setting for those seeking a quiet retreat within reach of Annapolis's attractions.

View 155+ Rentals in Arundel on the Bay

Eastport

Located along the waterfront, this charming community offers a vibrant harbor scene and convenient access to local dining and shopping options. It’s ideal for travelers wanting to immerse themselves in the local maritime culture.

View 71+ Rentals in Eastport

West Annapolis

This bustling neighborhood features a blend of historic charm and modern amenities, making it a great base for discovering the area's cultural attractions. Its walkable streets are perfect for exploring local cafes and boutiques.

View 710+ Rentals in West Annapolis

Oyster Harbor

Set along scenic waterways, Oyster Harbor offers picturesque views and a peaceful environment, perfect for outdoor enthusiasts. It’s a desirable location for enjoying outdoor activities while remaining close to the region's highlights.

View 220+ Rentals in Oyster Harbor

Murray Hill

Known for its welcoming community and lush landscapes, Murray Hill provides a comfortable setting for visitors looking for a quiet place to stay. It offers convenient access to both nature and city conveniences.

View 26+ Rentals in Murray Hill

Homewood

This historic neighborhood features elegant homes and tree-lined streets, offering a refined atmosphere for your stay. It’s a lovely area for those wanting to experience traditional charm with proximity to Annapolis's key sites.

View 722+ Rentals in Homewood

Hunt Meadows

A family-friendly neighborhood with spacious grounds and a suburban feel, Hunt Meadows is ideal for travelers seeking a peaceful retreat close to the area's attractions. It combines comfort with practicality for a memorable visit.

View 776+ Rentals in Hunt Meadows

Best Times to Visit Annapolis

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here can enhance your experience, as this destination offers different charms throughout the year, so consider the seasonal climate and local events to find the perfect period for your stay.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During these months, the area experiences warm weather and longer daylight hours, making it an ideal time to enjoy outdoor activities and explore the waterfront.

Average Temperature Daytime: 70-85Β°F - Nighttime: 55-65Β°F
autumn
Early Fall (September to October)

As autumn arrives, you’ll find pleasant temperatures and fewer crowds, offering a more relaxed experience while taking in the scenic beauty of the region.

Average Temperature Daytime: 68-80Β°F - Nighttime: 50-60Β°F

Off-Season Highlights

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Mid Winter (January to February)

The quiet winter months see cooler temperatures and less tourist activity, providing a peaceful setting for those seeking solitude and local charm.

Average Temperature Daytime: 40-50Β°F - Nighttime: 30-40Β°F
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Late Fall (November to December)

As the year winds down, the area becomes less crowded, and the festive season brings a cozy atmosphere perfect for exploring at a slower pace.

Average Temperature Daytime: 50-60Β°F - Nighttime: 40-50Β°F

Weekly Weather Forecast for Annapolis

How to Book Your Annapolis 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 Annapolis

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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 seating areas perfect for relaxing or entertaining under the Maryland sun.
  • Take advantage of private patios or decks that offer picturesque views of the surrounding waterfront or scenic landscapes.
  • Make the most of spacious yards or gardens for outdoor activities and gatherings in this charming region.
  • Look for outdoor grills or barbecue stations to prepare delicious meals during your stay here.
  • Relax in inviting hammocks or lounge chairs, ideal for soaking up the sunny weather in this coastal destination.
  • Utilize outdoor dining setups that allow you to enjoy meals while appreciating the area's natural beauty.
  • Access boat docks or mooring facilities for exploring the nearby waterways and embracing the region’s maritime spirit.

Top Attractions Around Annapolis

What attractions are nearby?

During your stay, you'll find a variety of nearby activities in the area, including scenic waterfront strolls, historic site visits, and charming local dining options that showcase the best of this destination.

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Family Activities

  • U.S. Naval Academy Tour: Explore this historic military academy, offering engaging guided tours perfect for family members interested in America's naval history and architecture.
  • Downtown Annapolis Waterfront Park: Spend a relaxing day at the park, where your family can enjoy scenic views of the Chesapeake Bay, playgrounds, and picnic areas in a lively maritime setting.
  • Lee's Park and Gardens: Discover the beautiful gardens and outdoor spaces that provide a peaceful environment for family strolls and nature exploration during your stay here.
  • Annapolis Maritime Museum: Learn about the region’s rich nautical heritage through interactive exhibits and boat tours, making it an educational experience for children and adults alike.
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Adult Activities

  • Cruise the Chesapeake Bay: Embark on a scenic boat tour to enjoy the stunning waters and maritime history that define this charming region.
  • Explore Historic Downtown Annapolis: Wander through streets filled with colonial architecture, boutique shops, and waterfront dining that showcase the area's rich heritage.
  • Visit the United States Naval Academy: Tour the prestigious institution and learn about its vital role in shaping naval history here in the region.
  • Enjoy Waterfront Dining: Savor fresh seafood and local cuisine at waterfront restaurants offering picturesque views of the Chesapeake Bay.

Other Places to Stay in Annapolis, MD

Northern Chesapeake Bay
Northern Chesapeake Bay Vacation Rentals
Historic District
Historic District Vacation Rentals
Parole
Parole Vacation Rentals
Kent Island
Kent Island Vacation Rentals
Bowie
Bowie Vacation Rentals
Eastport
Eastport Vacation Rentals
Stevensville
Stevensville Vacation Rentals
Edgewater
Edgewater Vacation Rentals
Selby-on-the-Bay
Selby-on-the-Bay Vacation Rentals
Arnold
Arnold Vacation Rentals
Severna Park
Severna Park Vacation Rentals
Murray Hill
Murray Hill Vacation Rentals
More Places to Stay Near Annapolis

Annapolis Travel Tips

How Can You Make the Most of Your Stay?

  • Explore the local waterfront: Take advantage of the scenic views by enjoying activities along the harbor, which offers a perfect backdrop for relaxation and exploration during your stay.
  • Visit historic districts: Immerse yourself in the area's rich history by walking through charming neighborhoods filled with well-preserved architecture and cultural landmarks.
  • Sample regional cuisine: Savor the flavors of the region with fresh seafood and local specialties at nearby eateries, enhancing your authentic experience here.
  • Plan outdoor adventures: Make the most of the pleasant climate by engaging in outdoor activities such as sailing, kayaking, or strolling through scenic parks around your rental property.

Transportation Options

  • Maryland Transit Administration (MTA) Bus Services: You can conveniently rely on local bus services for easy access to different parts of the area, making exploring Annapolis straightforward during your stay.
  • Water Taxi: Experience a scenic commute across the region’s waterways with water taxi services that offer a unique perspective of Annapolis and its surroundings.
  • Amtrak Train Service: The nearby train station provides comfortable rail options connecting you effortlessly to major cities and nearby destinations in the area.
  • Rental Cars: Renting a vehicle grants you flexible transportation, allowing you to explore both Annapolis and the surrounding region at your own pace.

Local Customs Options

  • Crab Feast Traditions: Participating in the local crab feasts is a beloved custom here, where you'll enjoy fresh Maryland blue crabs served with regional flair.
  • Yachting and Boating Etiquette: Embracing the region's maritime heritage involves understanding the etiquette surrounding yachting and boating, which are integral to the area's coastal lifestyle.
  • Historic Heritage Celebrations: Celebrating the area's history through events and parades offers an authentic way to connect with local customs rooted in Annapolis’s colonial past.
  • Fishing Practices: Engaging in or observing traditional fishing techniques reflects the region’s deep connection to its maritime environment and local livelihood.

Annapolis Vacation Rental Frequently Asked Questions

1. What is the cancellation policy for vacation rentals in Annapolis, Maryland?

The cancellation policy varies depending on the property listing. You should review the specific terms outlined in the listing details or contact the owner directly to understand the cancellation window and any applicable fees.

2. How do I ensure my booking in Annapolis is secure and reliable?

Booking through verified vacation rentals on this platform offers secure payment options and trusted hosts. Always read the reviews and confirm the property's legitimacy before making your reservation.

3. Are there any extra fees or charges associated with vacation rentals in this area?

Additional fees such as cleaning, service charges, or taxes may apply. These are typically detailed in the listing or during checkout, so be sure to review all costs before confirming your reservation.

4. What amenities are typically included in vacation rentals in Annapolis?

Most properties provide essential amenities like Wi-Fi, parking, and kitchen facilities. Specific features will depend on the individual listingβ€”be sure to check the property's description for what is included.

5. How far in advance should I book a vacation rental in this destination?

It's recommended to book several months ahead, especially during peak seasons, to secure your preferred property. Availability can vary, so early reservations help guarantee your stay.

Annapolis Top Rated Vacation Rentals

10.0 (87 Reviews)
House
Annapolis Entertainment Complex
  • Air Conditioner
  • Parking
  • Pet Friendly
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