Annapolis holiday lettings

We found 24 holiday rentals — enter your dates for availability
Discover a selection of 13 cabins and other holiday rentals in Annapolis that are perfect for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll find the best amenities for hanging out with the people that matter most, such as parking and air conditioning. At the end of the day, you'll be sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.
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Travel to relaxing Annapolis

The riverfront and parks create a pretty picture of Annapolis. Travellers appreciate the restaurants in this relaxing city. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Exploring the natural landscape of Annapolis

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Annapolis is a great spot to appreciate mother nature. Here are some of the area’s most stunning features, all within 30 miles (48.2 km) of the city centre:

  • K Bridge Recreation Area (4.2 mi / 6.7 km)
  • Clearwater Lake (15.7 mi / 25.3 km)
  • Walnut Hollow Lake (2.1 mi / 3.4 km)
  • Millstream Gardens Conservation Area (19.3 mi / 31 km)
  • Crane Lake Recreation Area (6 mi / 9.6 km)
  • Shepherd Mountain Bike Park and Hiking Trails (17.9 mi / 28.8 km)

Frequently asked questions

What is the best area to stay in Annapolis when booking a holiday rental?
When considering a holiday rental in Annapolis, Missouri, a great area to stay is near the scenic waterfront. This neighbourhood offers a charming atmosphere, with a variety of properties that cater to different preferences, from quaint cottages to more modern homes.

One of the top attractions in this area is the picturesque marina, where visitors can enjoy leisurely walks along the water, take part in boating activities, or simply relax and take in the stunning views. Additionally, the nearby historic district features beautifully preserved architecture, delightful shops, and inviting cafés, making it a wonderful spot for those interested in exploring local culture and history.

Moreover, visitors can easily access local parks that offer plenty of outdoor activities, great for families or anyone looking to enjoy nature.
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 particularly appealing. The neighbourhood of Eastport offers a vibrant setting with easy access to sandy shores and waterfront activities. Many properties here come equipped with amenities such as spacious decks, outdoor grills, and stunning bay views, making them great for family gatherings or relaxing getaways.

Along the shoreline, homes often feature private docks, ideal for those looking to enjoy boating or fishing. The proximity to the Annapolis Historic District allows for convenient exploration of charming shops and local restaurants, adding to the overall experience.

Additionally, nearby Sandy Point State Park provides ample opportunities for outdoor activities including swimming, picnicking, and hiking. Rentals in this area frequently include access to community facilities like swimming pools and tennis courts, enhancing the appeal for those seeking both relaxation and recreation.
What is the most popular type of holiday rental accomodation in Annapolis?
In Annapolis, cabins are the most popular type of holiday rental, with about 26 available in the area. These cabins often feature rustic charm, providing a cosy atmosphere with amenities like fully equipped kitchens, comfortable living spaces, and outdoor decks for enjoying the natural surroundings. Many of these rentals are set near picturesque landscapes, great for those looking to explore the outdoors.

In addition to cabins, there are several cottages and holiday houses available, offering travellers more options for their stay. These properties typically include multiple bedrooms, private outdoor spaces, and a range of amenities that cater to families or groups seeking a relaxing getaway.
Are there any family house rentals in Annapolis?
In Annapolis, Missouri, there are several family-friendly house rentals available. Visitors can find accommodations that provide ample space for families, often featuring multiple bedrooms and communal living areas to gather and relax. Many properties come equipped with full kitchens, allowing for convenient meal preparation, as well as outdoor spaces where children can play and adults can unwind.

The town offers a serene environment, superb for families looking to connect with nature. Nearby, the beautiful Lake of the Ozarks presents opportunities for fishing, boating, and hiking, ensuring there's plenty to keep everyone entertained. Additionally, the local area is known for its charming small-town atmosphere, which can enhance the overall experience for families seeking a peaceful getaway.
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 any remote work holiday rentals in Annapolis?
In Annapolis, Missouri, there are a number of remote work-friendly holiday rentals available, with around 30 options to choose from. These properties are well-suited for those looking to combine work and leisure, featuring amenities such as reliable Wi-Fi, free internet access in rooms, and designated workspaces. Many rentals offer comfortable living areas that can easily be transformed into productive work environments.

The area around Annapolis is serene, providing a peaceful backdrop for remote work, while also being close to natural attractions such as the nearby Ozark National Scenic Riverways. This unique setting allows for breaks in nature, with opportunities for hiking and exploring the beautiful landscapes of the region. 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, which allow travellers to prepare their own meals and enjoy home-cooked dining. Many properties are pet-friendly, accommodating those wishing to bring their furry companions along. Outdoor spaces such as decks or patios are common, providing a lovely area to relax and enjoy the surrounding nature. Onsite parking is also a typical feature, ensuring convenience for guests with vehicles. Additionally, rentals often come with coffee and tea makers, great for starting the day with a warm beverage.
When is the best time to visit Annapolis for a holiday rental?
The peak season for visiting Annapolis falls between June and August, with July being the most popular month for holiday rentals. During this vibrant period, the town comes alive with outdoor festivals, water activities, and opportunities to enjoy the stunning natural beauty of the Ozarks. Warm temperatures, typically ranging from 20 to 30 degrees Celsius, create a superb backdrop for hiking, fishing, and exploring the quaint downtown area.

If you're eager for a lively option filled with fellow travellers and local events, July is an excellent choice. You can immerse yourself in the community spirit as you partake in various summer festivities and enjoy the picturesque landscapes that Annapolis has to offer.

For those seeking a more budget-friendly option, consider visiting in March. This month offers a quieter experience, ideal for enjoying the natural beauty without the crowds. The scenery can be quite enchanting as the early signs of spring begin to emerge, making it a superb time for peaceful hikes or leisurely walks by the water.

Ultimately, the best time to book a holiday rental in Annapolis depends on whether you prefer the bustling energy of summer or the tranquil charm of early spring.
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, Missouri, visitors can explore several charming attractions that highlight the area's natural beauty and historical significance. The picturesque Lake of the Ozarks is a major draw, offering opportunities for fishing, boating, and swimming, making it a great spot for outdoor enthusiasts. Nearby, Ha Ha Tonka State Park features stunning rock formations, hiking trails, and the ruins of a 20th-century castle, providing a unique blend of history and nature.

The downtown area of Annapolis boasts quaint shops and local restaurants, superb for a leisurely stroll. Additionally, the nearby Ozark National Scenic Riverways provides excellent options for canoeing and kayaking, allowing visitors to immerse themselves in the region's scenic waterways.
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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