Historic District vacation rentals

We found 191 vacation rentals — enter your dates for availability

Discover a selection of 151 homes, 19 apartments, and other vacation rentals in Historic District that are perfect for your trip. Whether you’re staying in a vacation home with family or friends, you'll find the best amenities for hanging out with the people that matter most, such as parking and air conditioning. Whatever you're looking for, you're sure to find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Historic District

Showing deals for:Sep 12 - Sep 19
  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value
  • A place for everyone
    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Historic District

Find out more about Historic District

Why visit Historic District

  1. Historic Architecture: Explore beautiful vintage homes and historic buildings that reflect Annapolis's rich heritage.
  2. Scenic Parks: Enjoy outdoor activities in picturesque urban parks that offer relaxation and stunning views.
  3. Charming Marinas: Visit vibrant marinas where you can take in the waterfront scenery and indulge in water sports.
  4. Local Culture: Experience friendly locals, boutique shops, and inviting cafes that contribute to the area’s warm hospitality.
  5. Diverse Accommodations: Choose from unique vacation rentals, including cozy apartments and historic homes, enhancing your stay.

Popular types of accommodation around Historic District

If you’re exploring the Historic District, you’ll find a variety of exceptional vacation rentals to suit your needs. Our most popular options include charming houses, cozy apartments, and stylish apart-hotels. Whether you're looking for vintage homes, downtown Annapolis residences, or modern condos, we have the perfect place for you to stay and enjoy all that Annapolis has to offer.

  • Houses: The top choice for visitors to Historic District, offering spacious and versatile living for families or groups.
  • Apartments: A favored option for travelers seeking a comfortable and convenient stay, ideal for solo adventurers or couples.
  • Condos: These modern accommodations provide a blend of luxury and comfort, perfect for a stylish getaway.
  • Cottages: A charming choice, perfect for a snug and picturesque retreat.
  • House Boats: A unique and adventurous lodging option, allowing guests to enjoy life on the water.**

Top attractions around Historic District

Historic District in Annapolis, Maryland, is perfect for family, outdoor, and city vacations. Visitors can explore historic colleges and universities, scenic urban parks, and vibrant marinas, making it an ideal spot for culture and outdoor experiences. Don't miss the chance to tour vintage homes, which adds a unique touch to your trip. Enjoy all that this charming area has to offer while creating lasting memories with your loved ones.

  1. U.S. Naval Academy: Experience the rich history and tradition of naval education. Explore stunning architecture, beautiful grounds, and the Naval Academy Museum, showcasing naval history and art.
  2. Maryland State House: Discover the oldest state capitol still in continuous legislative use. This historic building offers a glimpse into Maryland's political heritage and stunning architecture, surrounded by vibrant culture.
  3. Chesapeake Bay Bridge: Marvel at this engineering marvel stretching across the bay. Enjoy breathtaking views of the water and cityscape, perfect for photography and an unforgettable experience.

Things to do recommended for couples

Looking for a romantic getaway in Annapolis? Enjoy an enchanting evening at the Ballet Theater of Maryland, explore the thrill of sailing with Annapolis Sailing School, or savor exquisite wines at Thanksgiving Farm Wines. Each experience is perfect for couples seeking adventure, culture, and romance.

Things to do recommended for families

Families visiting Historic District in Annapolis can enjoy the excitement of a game at Navy-Marine Corps Memorial Stadium, have fun at the Annapolis Bowl arcade, and relax in the serene surroundings of Fort Smallwood Park, perfect for wellness and family bonding.

Things to do recommended for groups

Explore the vibrant Westfield Annapolis Mall for shopping and entertainment, just 3 miles away. Enjoy a thrilling night at the Maryland Live Casino, 18 miles out, or challenge your friends to a round of golf at the U.S. Naval Academy Golf Club, only 2 miles from the Historic District.

What do I need to keep in mind when booking a vacation around Historic District

When planning your trip—whether you're traveling with a group, family, pets, or seeking extended stays—be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Historic District with a group: Think about how many bedrooms you require, as well as any additional features like a full kitchen or outdoor area for group gatherings. Thankfully, you can easily apply filters for these options and much more on Vrbo.
  • Traveling to Historic District with young kids: Traveling with young children can present some challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, thinking about your location in relation to family-friendly attractions can be very beneficial.
  • Taking your pets with you to Historic District: For many families, a trip wouldn’t feel complete without their furry companion. If that resonates with you, consider exploring Vrbo properties that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Historic District: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay around Historic District

Exploring the Historic District of Annapolis offers a delightful blend of family-friendly activities and romantic urban charm. Stroll through the picturesque downtown, where beautiful historic homes showcase the city's rich heritage. Discover vibrant neighborhoods filled with friendly locals, boutique shops, and inviting cafes. Whether you’re visiting with family or seeking a serene getaway, the Historic District promises an unforgettable experience steeped in history and warm hospitality.

  • Baltimore: Located approximately 22 miles from the Historic District, Baltimore is a vibrant metropolis known for its rich history and cultural diversity. Visitors are drawn to the city for its family-friendly attractions and business opportunities, as well as its lively city experience. Highlights include the famous Inner Harbor, where you can explore the National Aquarium and historic ships. The city also offers a variety of shopping centers and malls, making it a great destination for retail therapy. Don't miss the picturesque waterfront and local sports facilities, including stadiums for the Ravens and Orioles, adding to the excitement of your visit.
  • Naval Academy: Just 0.6 miles from the Historic District, the Naval Academy is a must-visit destination for those interested in culture and outdoor experiences. This iconic institution offers guided tours that provide insight into the life of midshipmen. The nearby shopping area features quaint boutiques and cafés perfect for a leisurely afternoon. The scenic dock port provides a stunning backdrop for photos and a relaxing stroll along the waterfront, making it ideal for families and tourists alike.
  • Murray Hill: Murray Hill, located only 0.6 miles from the Historic District, is a charming neighborhood that invites visitors to enjoy outdoor activities and a family-friendly atmosphere. With its recreational areas and local educational institutions, it’s a great spot for those looking to immerse themselves in the community. The area boasts beautiful parks and access to the beach, providing a perfect escape for relaxation and fun. Stroll through the picturesque streets, visit unique shops, and soak in the local charm.

Best time to go to Historic District

If you're planning a trip to Historic District, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from May to July, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January35.6°F (2.0°C)Light RainMostly SunnyModerately LowSlightly Low
February37.9°F (3.3°C)Light RainMostly SunnyModerately LowSlightly Low
March44.6°F (7.0°C)Light RainMostly SunnyAverageSlightly Low
April55.0°F (12.8°C)Light RainMostly SunnyAverageAverage
May64.2°F (17.9°C)Light RainMostly SunnyModerately HighAverage
June73.0°F (22.8°C)Light RainMostly SunnyAverageAverage
July78.4°F (25.8°C)Light RainMostly SunnyModerately HighSlightly High
August76.8°F (24.9°C)Light RainMostly SunnyModerately HighSlightly High
September70.7°F (21.5°C)Light RainMostly SunnyAverageAverage
October60.4°F (15.8°C)Light RainMostly SunnyAverageSlightly High
November48.7°F (9.3°C)Light RainMostly SunnyModerately LowAverage
December41.5°F (5.3°C)Light RainMostly SunnyAverageAverage

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate significantly. Also, extending your stay can result in substantial savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to refine your search by price, location, and type of vacation rental.

Save more with One Key

Reserve an eligible Vrbo for your group getaway and earn OneKeyCash™ on your booking. Being the planner has its perks! By enrolling in our travel rewards program, One Key, you can immediately access member savings and earn OneKeyCash™ on qualifying reservations. Sign up today and begin enjoying your savings!

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers an easy and organized way to plan your travels. You can create new trips, continue from where you last stopped, or view and arrange your existing plans. All your saved or booked properties will be neatly categorized into Potential, Upcoming, or Current Trips for your convenience. To begin using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Historic District?
Apartments are the most popular style of vacation rental in Historic District, according to our data. Even if you have a different vision in mind, Vrbo has vacation homes in many sizes and shapes. Browse our many options to find your perfect pad.
How much does it cost to rent a vacation rental in Historic District?
The average price for a vacation home in Historic District depends on several factors, including time of year, length of stay and property type. Whether you’re dreaming about a sprawling villa with space for extended family or a cozy cabin for just you and the kids, just add your dates of travel to see stays with exceptional value.
How much does it cost to rent a beach house in Historic District?
The average price for a vacation rental close to the beach in Historic District depends on when you’re traveling and the type and size of property you’re looking for. You can find prices quickly and easily on Vrbo by entering your travel dates. Then make use of the filter tool to select the number of bedrooms and amenities essential to you, like WiFi, air conditioning and a hot tub.
Are there pet-friendly vacation rentals in Historic District?
Yes. There are. You can choose from 123 vacation rentals that allow pets in Historic District. Plenty of our pet-friendly vacation rentals even come with an outdoor area for your fur baby to run around in, special dog beds, complimentary treats and proximity to parks. Apply the “Pets allowed” filter to find a pad that’ll set tails wagging on Vrbo.
What are popular rental amenities in Historic District?
A fireplace, a barbecue grill and a firepit head the list of most popular rental amenities in Historic District. Whether you’re planning to travel by yourself, with your spouse or a group of best friends, Vrbo will help you find a vacation rental that suits your style with a load of extras you’ll love.
Are there large group vacation rentals in Historic District?
With 19 vacation rentals that can sleep 10 guests or more in Historic District, there’s no need to leave anyone off your invite list. From fun family get-togethers to events like weddings and birthday parties, Vrbo will help you find a large group rental to suit the occasion.
Are there vacation rentals in Historic District that welcome kids?
Historic District has 118 family-friendly vacation rentals to choose from. And booking a stay that welcomes youngsters is a cinch with our “Properties good for families” filter. In addition to having the entire place to yourselves, you’ll also enjoy access to conveniences and perks like multiple bedrooms, kitchens and private pools.
What are the top attractions for families in Historic District?
Keep the kids busy at these fantastic family-friendly attractions in Historic District:

  • William Paca House
  • Annapolis City Dock
  • Ego Alley

Are there one-bedroom vacation rentals in Historic District?
Yes, Historic District has 12 one-bedroom rentals available. Often positioned in prime areas due to their smaller size, a one-bedroom vacation property is great if you’re getting away with your partner or a pal. And with plenty of home comforts like laundry facilities and more privacy than a standard hotel, you’ll be able to kick back and relax while enjoying this terrific destination.
Can I find two-bedroom vacation rentals in Historic District?
Historic District has 36 two-bedroom properties that you can choose from. Find a vacation home with all the comfort and privacy you’re looking for at a price that’s hard to resist on Vrbo.
Are there vacation rentals with WiFi in Historic District?
Whether you’d like to keep up with the news, make a video call or update your social media, there are 58 vacation homes with WiFi in Historic District. Check the “WiFi” box when searching on Vrbo and stay connected on your vacation.
How can I find vacation rentals with air conditioning in Historic District?
Historic District has 119 vacation rentals where you’ll be able to unwind in air-conditioned comfort. To locate a stay on Vrbo with this perk, enter your preferred travel dates and use the filters to select the “air conditioning” box.
How old do you have to be to rent a vacation rental in Historic District?
Age restrictions can vary across properties on Vrbo, so check the rules of the vacation rental in Historic District you’re considering. But in general, it’s 16, 18 or 21.
How long can I rent a vacation rental in Historic District for?
The amount of time you can rent a Historic District vacation rental for depends on each property. Just enter your travel dates to find available options that offer extended stays. They come with everything you need to make your extended break more comfortable and enjoyable, like air conditioning and kitchens. Some vacation rentals may also offer weekly or monthly discounted prices, so you can stay even longer for less.
Does Vrbo offer discounts for vacation homes in Historic District?
Whether you’re after one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you’re sure to find some fabulous bargains and discounts on Vrbo. From mini stays to extended getaways, we’ve got the perfect place for your next Historic District escape.

More Vacation Rentals ideas

People also search for