Annapolis holiday lettings

We found 746 holiday rentals — enter your dates for availability

Select from 401 houses, 55 apartments 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:26 Dec - 2 Jan

Image gallery for Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.

Kent Island Beach House:Winter, Spring, Summer & Fall there is something for All
10 out of 10, Exceptional, (76 reviews)
Exceptional
(76 reviews)

Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.

Stevensville, MD

8% off
Price is £5,053
for 7 nights, 1 home
£722 per night
includes taxes & fees
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find out more about Annapolis

Find out more about Annapolis

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:

  • U.S. Naval Academy Golf Club (1.9 mi / 3.1 km)
  • Maryland Renaissance Festival (5.4 mi / 8.6 km)
  • Renditions Golf Club (10.7 mi / 17.3 km)
  • Lake Presidential Golf Club (15.7 mi / 25.3 km)
  • Six Flags America (16 mi / 25.7 km)
  • Queenstown Harbor Golf Club (17.4 mi / 28 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)
  • Shadyside Park (9.2 mi / 14.8 km)
  • Fort Smallwood Park (11 mi / 17.6 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 District is the best area to stay. This charming neighbourhood is steeped in history and features a delightful array of historic architecture, quaint streets, and vibrant shops. One of the top attractions in this area is the Maryland State House, which is the oldest state capitol still in continuous use and offers fascinating insights into the state's history. The nearby U.S. Naval Academy is another must-visit, with its impressive campus and the opportunity to learn about naval traditions.

Another excellent area to consider is Eastport, which provides a lovely waterfront experience. This neighbourhood is known for its relaxed atmosphere and boasts stunning views of the Chesapeake Bay. Visitors can enjoy walking along the scenic waterfront or dining at one of the many delightful restaurants. The proximity to attractions such as the Annapolis Maritime Museum makes Eastport a fantastic choice for those interested in maritime history and local ecology.
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, Maryland, the area around the Chesapeake Bay offers some delightful options. The Broadneck Peninsula, particularly near Sandy Point State Park, provides holiday rentals with stunning views of the bay and easy access to sandy beaches. Many properties here come with amenities such as spacious decks, outdoor grills, and fully equipped kitchens, superb for families or groups wanting to enjoy the coastal lifestyle.

In the historic downtown Annapolis area, visitors can find charming waterfront homes that are just a short walk from the bustling shops, restaurants, and the iconic Maryland State House. These rentals often feature modern amenities like air conditioning, Wi-Fi, and comfortable living spaces, along with lovely outdoor areas for enjoying the pleasant weather.

Additionally, the nearby Eastport neighbourhood is known for its quaint charm and vibrant arts scene. Here, beach houses often come with access to private docks, making it a great choice for those interested in boating or fishing. Many properties in Eastport also boast amenities such as kayaks or paddleboards, ideal for water enthusiasts. Find your rental near the beach in Annapolis.
Are there any houseboat rentals in Annapolis?
In Annapolis, there are several houseboat holiday rentals available, offering a unique way to experience the charm of this historic city. These rentals are typically found in picturesque waterfront areas, providing stunning views of the Chesapeake Bay and easy access to local attractions like the United States Naval Academy and the Annapolis Historic District. Travellers can expect amenities such as fully equipped kitchens, comfortable living spaces, and outdoor decks great for enjoying the serene surroundings.
What is the most popular type of holiday rental accomodation in Annapolis?
In Annapolis, holiday houses are the most popular type of rental accommodation, with approximately 361 available throughout the area. These properties are typically located in charming neighbourhoods close to the historic district and the scenic waterfront, offering visitors a taste of local life. Most holiday houses come with multiple bedrooms, fully equipped kitchens, and outdoor spaces such as patios or gardens, great for enjoying the pleasant Maryland climate.

Apartments are also a popular choice, with around 45 rooms available, providing a more urban experience near attractions like the United States Naval Academy and the Maryland State House. These apartments often feature modern amenities, including open-plan living areas and convenient kitchen facilities.
Are there any family house rentals in Annapolis?
In Annapolis, Maryland, there are numerous family-friendly house rentals available, with around 301 options to choose from. This charming city, known for its maritime history and vibrant culture, offers a variety of neighbourhoods superb for families. Areas like Eastport provide beautiful waterfront views and easy access to attractions such as the Annapolis Maritime Museum, where children can learn about the region's nautical heritage.

Many of these homes come equipped with spacious living areas, full kitchens ideal for preparing family meals, and outdoor spaces for children to play safely. Amenities such as Wi-Fi and air conditioning are typically included, ensuring a comfortable stay for all ages. See all family-friendly rentals in Annapolis.
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 34 options to consider. This charming city, known for its rich maritime history and vibrant waterfront, offers a variety of neighbourhoods where travellers can find these properties. Areas such as Eastport provide scenic views and easy access to the water, while the Historic District features quaint streets lined with historic architecture.
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 a variety of options to accommodate travellers and their furry companions. The historic district features charming homes, many of which come equipped with modern amenities such as fully stocked kitchens, outdoor spaces, and comfortable living areas, making them ideal for families or groups.

Close to the water, you can find properties that offer easy access to the scenic waterfront, where pets can enjoy walks along the docks or nearby parks. One popular area is Quiet Waters Park, which provides lovely trails superb for leisurely strolls with pets. Additionally, the nearby Broadneck Park offers open spaces and walking paths, creating a welcoming environment for pets and their owners. See all pet-friendly rentals in Annapolis.
Are there any remote work holiday rentals in Annapolis?
In Annapolis, Maryland, there are plenty of options for remote work holiday rentals, with around 421 properties available throughout the area. Travellers can expect a variety of accommodations equipped with essential amenities for a productive stay. Many rentals feature dedicated office spaces, desks, comfortable chairs, and reliable Wi-Fi, ensuring a conducive work environment. 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 fully equipped kitchens, allowing guests to prepare their own meals comfortably during their stay. Many rentals also provide free Wi-Fi, ensuring visitors can stay connected while exploring the charming city. Additionally, you'll find microwaves, cookware, dishware, and utensils readily available in most rooms, making it easy to enjoy a home-cooked meal.
When is the best time to visit Annapolis for a holiday rental?
The best time to book a holiday rental in Annapolis is during the peak season from May to July, with July standing out as the most popular month. This vibrant period attracts visitors keen to explore the rich maritime culture, enjoy the picturesque waterfront, and partake in numerous festivals and events. The pleasant summer weather, with average temperatures in the mid-20s Celsius, makes it ideal for outdoor activities such as sailing, kayaking, and leisurely strolls along the historic district.

If you're seeking a more tranquil experience, consider visiting in November when you can enjoy the city's charm without the bustling crowds. This time of year is great for those who appreciate the beauty of autumn, as you can witness the transformation of the landscape and explore local shops and cafes at a leisurely pace.
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 explore a range of attractions that highlight the city's rich history and maritime culture. The historic district, with its beautifully preserved 18th-century architecture, features the Maryland State House, where George Washington famously resigned his commission. Nearby, the charming streets are lined with boutique shops, art galleries, and delightful restaurants, making it a superb area for those seeking a vibrant atmosphere.

The waterfront area offers picturesque views of the Chesapeake Bay and is home to the United States Naval Academy, which provides guided tours showcasing its impressive campus and naval heritage. Visitors can also enjoy the scenic City Dock, where they can watch boats come and go while sampling local seafood at nearby eateries.
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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

Explore destinations around Annapolis

More Holiday Rentals ideas

Olney Holiday Rentals
Standard Link for Olney
Rockville Holiday Rentals
Standard Link for Rockville
Tilghman Holiday Rentals
Standard Link for Tilghman
Ocean City Holiday Rentals
Standard Link for Ocean City
St. Michaels Holiday Rentals
Standard Link for St. Michaels
Key West Holiday Rentals
Standard Link for Key West
Salisbury Holiday Rentals
Standard Link for Salisbury
Sarasota Holiday Rentals
Standard Link for Sarasota
Lusby Holiday Rentals
Standard Link for Lusby
Davenport Holiday Rentals
Standard Link for Davenport
Gambrills Holiday Rentals
Standard Link for Gambrills
Adamstown Holiday Rentals
Standard Link for Adamstown
North East Holiday Rentals
Standard Link for North East
Chesapeake Beach Holiday Rentals
Standard Link for Chesapeake Beach
Epping Forest Holiday Rentals
Standard Link for Epping Forest
San Diego Holiday Rentals
Standard Link for San Diego
Taylors Island Holiday Rentals
Standard Link for Taylors Island
Stowe Holiday Rentals
Standard Link for Stowe
Naples Holiday Rentals
Standard Link for Naples
Palm Springs Holiday Rentals
Standard Link for Palm Springs
McHenry Holiday Rentals
Standard Link for McHenry
Destin Holiday Rentals
Standard Link for Destin
Berlin Holiday Rentals
Standard Link for Berlin
Severna Park Holiday Rentals
Standard Link for Severna Park
Gaithersburg Holiday Rentals
Standard Link for Gaithersburg
Friendsville Holiday Rentals
Standard Link for Friendsville
Hagerstown Holiday Rentals
Standard Link for Hagerstown

People also search for

Naples Villas
Standard Link for Naples
Rockville Apartments
Standard Link for Rockville
Gatlinburg Cabin Rentals
Standard Link for Gatlinburg