Best Vacation Homes in Annapolis
- Spa
- Fireplace/Heating
- Balcony/Terrace
- Fireplace/Heating
- Pet Friendly
- Parking
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Oceanfront
- Fireplace/Heating
- Ocean View
- Pet Friendly
- Parking
- Internet
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Ocean View
- View
- Pet Friendly
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
Annapolis Luxury Rentals
- Oceanfront
- Ocean View
- View
- Private Pool
- Fireplace/Heating
- Pool
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Private Pool
- Hot Tub
- Fireplace/Heating
- Private Pool
- Hot Tub
- Fireplace/Heating
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
Annapolis Pet Friendly Vacation Rentals
- Private Pool
- Spa
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Spa
- Fireplace/Heating
- Pool
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Hot Tub
- Fireplace/Heating
- Ocean View
Annapolis Large Vacation Homes
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Fireplace/Heating
- Pet Friendly
- Parking
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Oceanfront
- Fireplace/Heating
- Ocean View
- Fireplace/Heating
- Pet Friendly
- Parking
- Fireplace/Heating
- Air Conditioner
- Internet
- Private Pool
- Hot Tub
- Fireplace/Heating
- Oceanfront
- Hot Tub
- Fireplace/Heating
Why Choose Rent By Owner for your Annapolis Vacation Rental Homes?
What makes our Vacation Rentals special?
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 370+ Rentals in Historic DistrictArundel 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 BayEastport
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 54+ Rentals in EastportWest 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 796+ Rentals in West AnnapolisOyster 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 235+ Rentals in Oyster HarborMurray 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 809+ Rentals in Murray HillHomewood
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 815+ Rentals in HomewoodHunt 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 825+ Rentals in Hunt MeadowsBest 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
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.
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.
Off-Season Highlights
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.
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.
Weekly Weather Forecast for Annapolis
How to Book Your Annapolis Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Annapolis
Common Vacation Rentals 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 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.
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.
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
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 are the top vacation rentals in Annapolis?
There are a lot of options in Annapolis. If you plan on staying in the Annapolis area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Annapolis:
- Annapolis waterfront "tiny house" in garden setting
- Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
- Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
- PERFECT LOCATION in the heart of history
- Stunning Waterfront Cottage in the Sailing Capital of the World!
- Ultraclean Family Waterfront Home Annapolis Area - 200+ Top Reviews!
- Charming Historic Annapolis Home With Two Off-street Parking Places!
- Island Life! Kent Island Waterfront with Pool-Bring your boat!
- 240' Private Beachfront @Kent Island Love Point - Great for Families
- Renovated Apt In Historic Dist w/2 Parking Spots
2. How many vacation rentals have private pools in Annapolis?
There are 69 vacation rentals with private pools near Annapolis. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Annapolis are best for families?
If you are looking for a family-friendly vacation home in Annapolis, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Annapolis:
4. How many Rentbyowner vacation rentals are available in Annapolis?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 1351 in the Annapolis 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 Annapolis.
5. What is the cancellation policy for vacation rentals in Annapolis, Maryland?
6. How do I ensure my booking in Annapolis is secure and reliable?
7. Are there any extra fees or charges associated with vacation rentals in this area?
8. What amenities are typically included in vacation rentals in Annapolis?
9. How far in advance should I book a vacation rental in this destination?
Annapolis Top Rated Vacation Rentals
- Private Pool
- Fireplace/Heating
- Pool
- Private Pool
- Fireplace/Heating
- Pool
- Private Pool
- Hot Tub
- Fireplace/Heating
- Private Pool
- Hot Tub
- Fireplace/Heating
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Private Pool
- Fireplace/Heating
- Pool
- Private Pool
- Fireplace/Heating
- Pool
- Private Pool
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