Annapolis holiday lettings

We found 713 holiday rentals — enter your dates for availability

Select from 378 houses, 26 flats and other holiday rentals to find the perfect place for your stay in Annapolis. Whether you’re travelling with friends, family or even pets, holiday rentals have the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a washer and dryer. You'll be able to choose a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Annapolis

Showing deals for:3 Jul - 10 Jul

Image gallery for USNA Stay w indoor Soft Hot Tub, Private Pool, King Beds & CHILD FRIENDLY GEAR

View from the front of this Stately Masterpiece (you'd think I built it ;-)
8.0 out of 10, Very good, (5 reviews)
Very good
(5 reviews)

USNA Stay w indoor Soft Hot Tub, Private Pool, King Beds & CHILD FRIENDLY GEAR

Annapolis

15% off
Price is £6,803
for 7 nights, 1 home
£972 per night
includes taxes & fees
USNA Stay w indoor Soft Hot Tub, Private Pool, King Beds & CHILD FRIENDLY GEAR

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Why visit Annapolis

  • Historic charm: Annapolis is rich in history, featuring well-preserved historic houses and landmarks that tell tales of its past.
  • Scenic waterfront: The city boasts beautiful marinas and waterfront parks, perfect for leisurely walks and outdoor activities.
  • Family-friendly attractions: There are numerous activities suitable for families, ensuring a delightful experience for visitors of all ages.
  • Vibrant downtown: The lively downtown area offers shopping, dining, and cultural experiences, ideal for leisurely exploration.
  • Outdoor adventures: Nearby Kent Island provides a gateway to various outdoor pursuits, from hiking to water sports.

Popular types of accommodation in Annapolis

At Vrbo, we offer a variety of accommodations in Annapolis to suit every traveller's needs. Whether you're seeking a charming private holiday home, a cozy cottage, or a stylish apartment, you'll find the perfect place to stay in Annapolis. Explore our selection of house rentals and condo rentals, and enjoy a memorable getaway with family or friends in this beautiful coastal city.

  • Houses: The top choice for visitors to Annapolis, offering spacious and comfortable accommodations perfect for families or groups of friends.
  • Cottages: A delightful option for a quaint and charming retreat, ideal for those seeking a peaceful getaway.
  • Apartments: A convenient and modern choice, providing the comforts of home in the heart of the city.
  • Condos: A stylish alternative, often featuring amenities like pools and fitness centres, perfect for a relaxing stay.
  • Villas: Luxurious accommodations that offer ample space and high-end features for an indulgent holiday experience.**

Top attractions in Annapolis

Annapolis is perfect for families and those seeking a city-themed or outdoor getaway. Visitors can enjoy an array of attractions, including urban parks, marinas, and historic houses. The points of interest in and around Annapolis provide excellent opportunities for outdoor activities, cultural experiences, and family-friendly fun, ensuring there's something for everyone to enjoy during their stay.

  • U.S. Naval Academy: A historic institution showcasing military tradition and stunning architecture. Explore the beautiful grounds and visit the Naval Academy Museum for a glimpse into the naval heritage of the United States.
  • Chesapeake Bay Bridge: An impressive modern marvel that offers breathtaking views of the bay. Experience the vibrant city vibes as you walk or drive across this iconic structure, linking Maryland's eastern and western shores.
  • Sandy Point State Park: A delightful national park perfect for outdoor adventures. Enjoy hiking, picnicking, and stunning waterfront views, making it an ideal spot for nature lovers and families alike.

Things to do recommended for couples

For a romantic getaway in Annapolis, embark on a sailing adventure with the Annapolis Sailing School, indulge in a captivating performance at the Ballet Theater of Maryland, or enjoy a delightful wine tasting at Thanksgiving Farm Wines, located a mere 6.2km away. Perfect for couples seeking memorable experiences!

Things to do recommended for families

Families visiting Annapolis can immerse themselves in the sports atmosphere at the Navy-Marine Corps Memorial Stadium, enjoy thrilling games at the Annapolis Bowl arcade, and unwind at Fort Smallwood Park, a serene spot just 6.8km away, perfect for relaxation and wellness activities.

Things to do recommended for groups

Groups visiting Annapolis can indulge in a shopping spree at the Westfield Annapolis Mall, enjoy a round of golf at the nearby Bay Hills Golf Club, or experience local culture and romance at The Colonial Players theatre, ensuring a delightful blend of activities for everyone.

What do I need to keep in mind when booking a vacation in 'Annapolis

If you're travelling with a group, family, pets, or seeking longer stays, be sure to refine your search based on your key preferences. Here are some helpful Vrbo booking tips for you.

  • Traveling to Annapolis with a group: Think about how many bedrooms you require, along with features like a fully-equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily refine your search for these options and much more on Vrbo.
  • Traveling to Annapolis with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, as well as seek out age-appropriate facilities, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Annapolis: For many, a family holiday wouldn't feel complete without their furry companion by their side. If you can relate to this, take a look at 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 Annapolis: If you’re in search of holiday rentals that offer discounts for stays of a month or more, you’ve come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features such as a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Annapolis

Annapolis, a charming city steeped in history, offers delightful experiences for families and city explorers alike. The vibrant downtown is perfect for leisurely strolls, while nearby Kent Island invites outdoor adventures. The Annapolis area is renowned for its friendly atmosphere and rich heritage, ensuring a memorable holiday filled with excursions and family-friendly activities. Discover the ideal blend of relaxation and exploration in this captivating destination.

  • Historic District: Nestled in the heart of Annapolis, the Historic District offers visitors a charming blend of history and modernity. With its cobblestone streets and colonial architecture, this area invites you to explore its rich heritage. Families will enjoy leisurely strolls while uncovering local landmarks such as the academy and the bustling dock port. The district is also a hub for shopping, featuring quaint boutiques and a vibrant shopping mall centre, perfect for those seeking a unique retail experience.
  • Parole: Located near Annapolis, Parole is a quaint village that caters to families and business travellers alike. This community boasts a range of educational facilities and a prominent shopping centre, ensuring that visitors have everything they need at their fingertips. Notable attractions include a pristine beach and a local stadium, making it an excellent spot for sports enthusiasts. Parole provides a delightful atmosphere for both relaxation and exploration, all within easy reach of Annapolis.
  • Eastport: Just a stone's throw from Annapolis, Eastport is a vibrant neighbourhood known for its outdoor activities and family-friendly environment. The area features a mix of educational facilities and recreational spaces, encouraging visitors to engage with nature. Highlights include the scenic beach and a lively tourist precinct, which is perfect for soaking in the local culture. Eastport's charming waterfront adds to its allure, making it an ideal destination for those looking to immerse themselves in the beauty of the Chesapeake Bay.

Best time to go to Annapolis

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 SunnyModerately LowSlightly Low
April55.0°F (12.8°C)Light RainMostly SunnyAverageAverage
May64.2°F (17.9°C)Light RainMostly SunnyAverageAverage
June73.0°F (22.8°C)Light RainMostly SunnyModerately HighSlightly High
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 SunnyAverageAverage
November48.7°F (9.3°C)Light RainMostly SunnyAverageAverage
December41.5°F (5.3°C)Light RainMostly SunnyAverageAverage

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can make a real difference, as prices often fluctuate. Additionally, opting for a longer stay can lead to substantial savings. To discover a Vrbo property that suits your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's clever Trip Board offers you a dedicated area to craft new trips, pick up from where you last paused, or review and manage your travel plans. You can easily locate properties you've previously saved and booked under Potential, Upcoming, or Current Trips. To explore Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Historical Annapolis will entice you

The area's history and live music are just some of the reasons to come on holiday to Annapolis. Renowned for its university setting, shopping and restaurants, this city welcomes all visitors. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Annapolis

Do you want to find attractions to see in the area? Venture out of your holiday home and check out everything that makes Annapolis a fun place to get away to. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Bay Hills Golf Club (4.7 mi / 7.6 km)
  • Maryland Renaissance Festival (5.4 mi / 8.6 km)
  • Renditions Golf Club (10.7 mi / 17.3 km)
  • Queenstown Harbor Golf (17.4 mi / 28 km)
  • St. Michaels Winery (19.9 mi / 32.1 km)
  • Chesapeake Beach Water Park (19.9 mi / 32.1 km)

Exploring the natural landscape of Annapolis

Whether you're looking for adventure or just want to spend some time taking in the scenery, Annapolis is a great place to spend some time outside. These are some of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Carrs Beach (2 mi / 3.3 km)
  • Maryland Quiet Waters Park (2.4 mi / 3.9 km)
  • Bay Ridge Beach (2.9 mi / 4.6 km)
  • Sandy Point Beach (5.7 mi / 9.2 km)
  • Triton Beach (6.6 mi / 10.6 km)
  • Northern Chesapeake Bay (8 mi / 12.8 km)

Transport to and around Annapolis

Fly into Fort Meade, MD (FME-Tipton), the closest airport, located 16.2 mi (26.1 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Baltimore Washington International Airport (BWI), which is 16.8 mi (27 km) away.

Frequently asked questions

What is the best area to stay in Annapolis when booking a holiday rental?
When considering a holiday rental in Annapolis, Maryland, the historic downtown area is one of the best choices. This charming neighbourhood is steeped in history and offers a vibrant setting, making it a favourite among visitors. Here, you'll find a delightful array of properties, from quaint cottages to elegant townhouses. The proximity to the waterfront is a major draw, allowing easy access to scenic views and leisurely strolls along the docks.

One of the top attractions in downtown Annapolis is the Maryland State House, the oldest state capitol still in continuous use, which showcases stunning architecture and rich American history. Another highlight is the United States Naval Academy, where you can explore its beautiful grounds and learn about its storied tradition. The area's cobblestone streets are lined with charming boutiques, restaurants, and galleries, providing plenty of options for dining and shopping.

If you prefer a more residential feel, Eastport is another excellent choice. This neighbourhood, just across the water from downtown, offers a mix of waterfront properties and cosy homes, along with a relaxed vibe. Eastport is known for its local eateries and boutique shops, and it's just a short walk or boat ride from the bustling downtown area.
How much does it cost to rent a holiday home in Annapolis?
Prices for holiday rentals in Annapolis vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Annapolis to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Annapolis holiday house rentals?
You can find great discounts on house rentals in Annapolis on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Annapolis?
For renting a beach house in Annapolis, the area around the Chesapeake Bay is highly desirable. The Eastport neighbourhood, located just across the water from downtown Annapolis, is particularly popular for its charming waterfront properties. Many rentals here offer stunning views of the bay, private docks, and easy access to local marinas, making them superb for those interested in boating or fishing. Guests can expect amenities such as spacious decks for outdoor dining, modern kitchens, and comfortable living areas, ideal for family gatherings or relaxing after a day on the water.

Another great option is the Cape St. Claire community, which features a mix of traditional beach cottages and more modern homes. This area provides a laid-back atmosphere with access to sandy beaches and picnic areas, along with amenities like outdoor showers, fire pits, and community facilities. Visitors can enjoy local parks and trails, superb for walking or cycling, and the proximity to local shops and restaurants adds to the convenience.

For those looking for a more secluded experience, the properties along Broadneck Park offer a tranquil setting with easy access to the bay. Rentals in this area often include features like large yards, private balconies, and family-friendly amenities, making them an excellent choice for travellers seeking a peaceful retreat while still being close to the attractions of Annapolis.
Are there any houseboat rentals in Annapolis?
In Annapolis, there are about 16 houseboat holiday rentals available, primarily located along the scenic waterfront and in marinas close to the historic district. These unique accommodations offer a blend of nautical charm and modern comfort, with most featuring amenities such as fully equipped kitchens, spacious living areas, and outdoor decks superb for enjoying the views of the Chesapeake Bay. Many houseboats are conveniently situated near popular attractions like the United States Naval Academy and the vibrant City Dock, allowing guests to immerse themselves in the local culture and dining options.
What is the most popular type of holiday rental accomodation in Annapolis?
In Annapolis, holiday houses are the most popular type of holiday rental, with around 1,204 available throughout the city. These properties are often located in charming neighbourhoods close to the historic district, providing easy access to attractions such as the United States Naval Academy and the waterfront. Most holiday houses come equipped with multiple bedrooms, spacious living areas, and fully equipped kitchens, allowing guests to enjoy a home-like experience.

Apartments are also a top option, with approximately 180 available, typically featuring modern amenities and convenient locations near local shops and restaurants. For those seeking a great experience, there are about 88 cottages and 88 condos, which often provide picturesque views and outdoor spaces for relaxation. Additionally, a few houseboats are available for a distinctive stay on the water.
Are there any family house rentals in Annapolis?
In Annapolis, Maryland, there are numerous family-friendly house rentals available, with around 257 options throughout the city. This charming area is known for its maritime heritage, historic architecture, and vibrant waterfront, making it an excellent choice for families. Many properties in neighbourhoods such as Eastport and the Historic District offer spacious living areas, fully equipped kitchens, and outdoor spaces that are superb for children to enjoy.

Visitors can find amenities like Wi-Fi, air conditioning, and sometimes even features such as game rooms or backyards with grills, enhancing the family experience. Moreover, being close to attractions like the U.S. Naval Academy, the Maryland State House, and the picturesque City Dock allows families to easily engage in educational and recreational activities together.
Can I rent a holiday home with a pool or hot tub in Annapolis?
In Annapolis, there are several holiday homes available for rent that feature pools and hot tubs, with around 38 options to choose from. This charming city, known for its maritime heritage and historic architecture, offers a variety of neighbourhoods where these properties can be found, including the picturesque Eastport area, which is close to the waterfront and offers stunning views, and the quaint Historic District, where visitors can explore cobblestone streets and local shops.

Travellers can expect a range of amenities in these rentals, including private swimming pools, relaxing hot tubs, and spacious outdoor areas for entertaining. Many properties also come with fully equipped kitchens, allowing for convenient meal preparation, and some may feature additional luxuries such as outdoor dining spaces, fire pits, and easy access to local attractions.
Can I find long-stay holiday rentals in Annapolis?
A long-stay holiday rental in Annapolis is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Annapolis?
In Annapolis, there are numerous pet-friendly house rentals available, with around 149 options to choose from. The city offers a charming blend of historic architecture and waterfront views, making it a delightful destination for pet owners. Many holiday rentals come equipped with amenities such as spacious backyards, fully stocked kitchens, and comfortable living areas, allowing for a relaxing stay with your furry companions.

The neighbourhood around the historic district is particularly appealing, with properties that provide easy access to local parks and the scenic waterfront. The nearby Quiet Waters Park features lovely walking trails and open spaces, superb for exercising pets, while the Broadneck Park offers additional recreational areas for outdoor activities. Additionally, the city's dog-friendly cafes and shops enhance the experience for travellers with pets, ensuring both comfort and convenience during their stay. See all pet-friendly rentals in Annapolis.
Are there any remote work holiday rentals in Annapolis?
In Annapolis, there are a significant number of remote work holiday rentals available, with around 1,492 options to choose from. This charming city, known for its rich maritime history and vibrant culture, provides an excellent backdrop for those looking to blend work and leisure. Many of these properties come equipped with essential amenities for remote work, including reliable Wi-Fi, dedicated workspaces or desks, and comfortable living areas that allow for a productive environment.

Travellers can expect a variety of accommodations, ranging from quaint cottages to spacious homes, often featuring modern kitchens and outdoor spaces great for a break from work. The historic downtown area, with its picturesque streets and waterfront views, offers plenty of opportunities for relaxation after a day of remote working. Additionally, the proximity to local attractions such as the United States Naval Academy and the scenic Annapolis Harbor adds to the appeal. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Annapolis holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Annapolis with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Annapolis?
In Annapolis, popular rental amenities include well-equipped kitchens, which allow guests to prepare meals during their stay. Many properties also feature decks or patios, providing outdoor spaces to relax and enjoy the pleasant Maryland weather. A coffee and tea maker is commonly found in rentals, ensuring visitors can enjoy their morning brew at their convenience. Onsite parking is another sought-after amenity, making it easier for guests to explore the historic downtown area and the scenic waterfront.
When is the best time to visit Annapolis for a holiday rental?
The best time to visit Annapolis for a holiday rental is during the peak season from May to July. This vibrant period is particularly popular among travellers looking to enjoy the city's rich maritime culture and beautiful waterfront. With warm temperatures averaging between 20 to 30 degrees Celsius, it's an ideal time for outdoor activities such as sailing, kayaking, and exploring the historic streets lined with charming shops and eateries.

July stands out as the most popular month, attracting families and groups eager to experience the lively option created by festivals and events, including the renowned Annapolis Arts & Wine Festival. Visitors can take advantage of longer daylight hours to soak in the sights, making it a truly delightful experience.

For those looking to maximise their budget while still enjoying the beauty of Annapolis, consider a trip in November. This month, while quieter, offers a unique charm with fewer crowds, allowing for leisurely strolls through the picturesque downtown and the chance to enjoy local dining without the rush of peak season.
How early should I book a Annapolis holiday rental?
Book your Annapolis holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Annapolis?
In Annapolis, visitors can take part in a rich maritime heritage and vibrant culture. The historic district is a must-see, featuring charming historic architecture and attractions like the Maryland State House, where the Continental Congress once met. Here, holiday rentals often reflect the area's history and provide easy access to local shops and restaurants.

The United States Naval Academy is another key attraction, offering guided tours that showcase its impressive grounds and museums. Nearby, the scenic waterfront along City Dock is superb for leisurely strolls and dining, with stunning views of the boats and the Chesapeake Bay.

For those who appreciate nature, Sandy Point State Park provides a beautiful setting for picnics, hiking, and beach activities, all just a short drive from the city centre.
Can I change or cancel my Annapolis home rental booking on Vrbo?
To find Annapolis holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Annapolis holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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