Annapolis vacation rentals

We found 21 vacation rentals — enter your dates for availability

Discover a selection of 12 cabins and other vacation rentals in Annapolis that are perfect for your trip. Whether you’re staying in a vacation home with friends, family, or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include cable TV and a washer and dryer. Whatever you're looking for, you'll be able to choose a rental for everyone's needs, including a place that is accessible or non-smoking.

Find out more about Annapolis

Find out more about Annapolis

Why visit Annapolis

  1. Outdoor Adventures: Annapolis is perfect for hiking, fishing, and exploring nature in its beautiful parks and lakes.
  2. Scenic Wappapello Lake: Enjoy breathtaking views and a variety of recreational activities at this stunning lake.
  3. Charming Fredericktown: Nearby Fredericktown offers delightful dining options and a friendly atmosphere to explore.
  4. Welcoming Community: Experience the warmth of the local community, ideal for family-friendly activities and relaxation.
  5. Cozy Vacation Rentals: Choose from a range of vacation homes, including cabins and cottages, for a perfect getaway.

Popular types of accommodation in Annapolis

Planning a getaway to Annapolis? You’re in for a treat! With a variety of options, the most popular vacation rentals include cozy cabins, charming private homes, and delightful cottages. Whether you’re considering a Hillside Cabin, the Redford Cabin, or exploring Iron Township cabin rentals, you’ll find the perfect spot to unwind. Dive into the vibrant culture of Annapolis while enjoying the comforts of your home away from home!

  • Cabins: A favorite among visitors, cabins offer a cozy and rustic escape, perfect for those wanting to connect with nature.
  • Houses: Ideal for families and groups, these homes provide spacious accommodations and a home-like atmosphere.
  • Cottages: Charming and quaint, cottages offer a warm, inviting setting for a peaceful getaway.
  • Apartments: Convenient and comfortable, apartments are great for travelers seeking a modern stay with easy access to amenities.
  • Caravan Parks: A budget-friendly option, caravan parks allow for adventurous stays with access to outdoor activities.**

Top attractions in Annapolis

Annapolis, Missouri, is a fantastic destination for outdoor enthusiasts and adventure seekers. With its stunning scenery, visitors can explore national and state parks, serene lakes, and inviting urban parks. Whether you're looking to hike, fish, or simply enjoy nature, Annapolis offers a variety of attractions that cater to your adventurous spirit. Embrace the great outdoors and discover the beauty of this charming town on your vacation!

  1. K Bridge Recreation Area: This urban park offers a family-friendly atmosphere with plenty of outdoor activities. Enjoy walking trails, picnics, and the vibrant city vibes while soaking in the natural beauty of Annapolis.
  2. Walnut Hollow Lake: A romantic getaway featuring serene beach vibes and stunning scenery. Perfect for swimming, fishing, or simply relaxing by the water, this lake is an ideal spot for couples and nature lovers alike.
  3. Taum Sauk Mountain State Park: Located 15 miles from Annapolis, this national park is a haven for adventure seekers. With breathtaking views and numerous hiking trails, it promises an unforgettable outdoor experience.

Things to do recommended for families

Your family will love visiting the Crane Lake Recreation Area, just 6 miles from Annapolis, which offers a serene atmosphere perfect for relaxation. You can also explore the Silver Mine Recreation Area, located 20 miles away, providing additional outdoor fun and wellness experiences for everyone.

Things to do recommended for groups

Enjoy a round of golf at the Arcadia Valley Golf Club, just 17 miles from Annapolis, or embark on an adventure at the Shepherd Mountain Bike Park and Hiking Trails, located 18 miles away, where you can soak in the beautiful outdoor scenery.

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

When planning your trip, whether you're traveling with a group, as a family, with pets, or seeking extended stays, be sure to use the appropriate filters to meet your specific needs. Here are some helpful booking tips for Vrbo.

  • Traveling to Annapolis with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Annapolis with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with providing suitable amenities, 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 families, a trip wouldn’t feel complete without their furry companions. If you can relate, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer 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 vacation rentals that offer special deals for month-long stays, 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 amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Annapolis

Annapolis, Missouri, offers a delightful blend of outdoor adventures and scenic beauty. Explore Wappapello Lake for breathtaking views and recreational activities, while Fredericktown nearby provides a charming atmosphere with delicious dining options. Stroll through the friendly streets of Annapolis, where you'll find a welcoming community perfect for family-friendly experiences and relaxation. Whether you seek adventure or tranquility, Annapolis promises a memorable vacation filled with friendly faces and rich local history.

  • Van Buren: Located 31 miles from Annapolis, Van Buren is a haven for outdoor enthusiasts and adventure seekers. The city is surrounded by stunning natural landscapes, making it an ideal destination for hiking, fishing, and exploring. Visitors can enjoy the scenic beauty of the nearby Ozark National Scenic Riverways, where opportunities for kayaking and canoeing abound. The local recreational areas offer various amenities, including picnic spots and trails, while the entertainment facilities provide a fun atmosphere for families. The iconic landmarks, including the picturesque rivers and sprawling state parks, make Van Buren a must-visit stop on your itinerary.
  • Ironton: Just 17 miles away from Annapolis, Ironton is another gem for those who love nature and adventure. Nestled in the foothills of the Ozarks, this charming city provides access to expansive recreational areas and national parks, perfect for hiking, camping, and wildlife viewing. Ironton's nearby forests showcase stunning fall colors and offer trails for all skill levels. The local arena entertainment facilities host various events, adding to the vibrant community spirit. With its close proximity to breathtaking landscapes, Ironton invites travelers to immerse themselves in outdoor activities and appreciate the scenic vistas.
  • Lesterville: Located only 10 miles from Annapolis, Lesterville is a picturesque town known for its outdoor allure and serene atmosphere. The area is a playground for those who love fishing, swimming, and tubing along the beautiful rivers. Lesterville's recreational areas are equipped with facilities for a day of family fun, while the nearby national parks provide an opportunity to experience the rich biodiversity of the region. Whether you're looking to hike the trails or relax by the water, Lesterville offers a peaceful retreat with stunning natural beauty, making it an essential stop on your journey.

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 in June to July and September, while off-peak times, like January, March and November tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January34.5°F (1.4°C)Light RainMostly SunnySlightly LowAverage
February37.8°F (3.2°C)Light RainMostly SunnyAverageSlightly Low
March48.0°F (8.9°C)Light RainMostly SunnySlightly LowSlightly High
April56.8°F (13.8°C)Light RainMostly SunnyAverageAverage
May66.4°F (19.1°C)Light RainMostly SunnyAverageAverage
June75.7°F (24.3°C)Light RainMostly SunnySlightly HighAverage
July79.0°F (26.1°C)Light RainMostly SunnySlightly HighSlightly High
August77.0°F (25.0°C)Light RainMostly SunnyAverageSlightly High
September70.7°F (21.5°C)Light RainMostly SunnySlightly HighAverage
October59.0°F (15.0°C)Light RainMostly SunnyAverageAverage
November46.9°F (8.3°C)Light RainMostly SunnySlightly LowSlightly Low
December39.4°F (4.1°C)Light RainMostly SunnyAverageSlightly Low

Booking with Vrbo is simple

Planning to save on your upcoming trip? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, booking a longer stay can lead to considerable savings. To discover a Vrbo property that aligns with your budget, take advantage of our filters to narrow down your options by price, location, and type of vacation rental.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your entire booking. Being the planner truly has its rewards! By signing up for our travel rewards program, One Key, you can access exclusive discounts and accumulate OneKeyCash™ on eligible reservations. Join today and begin enjoying your savings!

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers a user-friendly platform for planning your travels, allowing you to create new trips, continue from where you last paused, or view and manage your itinerary. You can easily find your saved or booked properties organized into categories like Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/trips.

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

Travel to tranquil Annapolis

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

Exploring the natural landscape of Annapolis

Whether you're an adventurous traveler or just want to spend some time taking in the scenery, Annapolis is a great place to get outside. Here are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • K Bridge Recreation Area (4.2 mi / 6.7 km)
  • Clearwater Lake (15.7 mi / 25.3 km)
  • Silver Mine Recreation Area (19.7 mi / 31.7 km)
  • Walnut Hollow Lake (2 mi / 3.3 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 most popular type of vacation rental accommodation in Annapolis?
According to our research, cabins are the most popular type of vacation rental in Annapolis. But as you might expect, everyone’s idea of an awesome trip can vary. Vrbo has vacation rentals of all shapes and sizes, so you’re sure to discover your ideal match.
How much does it cost to rent a vacation rental in Annapolis?
The average price for a vacation rental in Annapolis can vary based on factors such as length of stay, season and property type. Whether you’re dreaming about a sprawling villa with lots of space or a cozy condo perfect for just you and the kids, just enter your travel dates to view stays with exceptional value.
How much does it cost to rent a beach house in Annapolis?
The average price for a vacation home close to the beach in Annapolis depends on when you’ll be there 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 and destination. Then use our handy filter tool to select the number of bedrooms and amenities that you prefer, such as WiFi, air conditioning and a pool.
Are there pet-friendly vacation rentals in Annapolis?
Pack a travel bag and a bone for your pooch because Annapolis has 12 properties that throw out the welcome mat to pets. Let your furriest friend have fun with the family at one of our pet-friendly vacation rentals on Vrbo. Simply enter your travel dates and destination, then check the “Pets allowed” filter box.
What are popular rental amenities in Annapolis?
When it comes to rental amenities that people prefer in Annapolis, a garden, a barbecue grill and a water view are at the top of the list. With Vrbo vacation rentals, there are choices to suit your style and taste, whether you’re planning to get away with family members, friends or even pets.
Are there large group vacation rentals in Annapolis?
With four vacation rentals that can sleep 10 or more guests in Annapolis, there’s no need to cross anyone off the invite list. From fun family vacations to events like Christmas or New Year’s Eve parties, Vrbo will help you find a large group rental to suit the occasion.
Are there vacation rentals in Annapolis that welcome kids?
With 12 family-friendly vacation properties to pick from in Annapolis, there’s never been a better time to introduce your little ones to the thrills of travel. Simply check our “Properties good for families” filter box to look for stays that feature amenities ideal for traveling families, like multiple bedrooms, outdoor spaces, entertainment areas and bunk beds.
What are the top attractions for families in Annapolis?
If you’ve got the kids in tow, put these family-friendly attractions in Annapolis on your to-do list:

  • Walnut Hollow Lake
  • K Bridge Recreation Area

Are there one-bedroom vacation rentals in Annapolis?
There are three one-bedroom properties in Annapolis to pick from. A one-bedroom vacation rental is an excellent option if it’s only the two of you or if you’re vacationing alone. Toss in more convenience, privacy and space compared to a regular hotel, and you’ve got yourself a break to remember.
Can I find two-bedroom vacation rentals in Annapolis?
You can select from three two-bedroom homes in Annapolis. Put the kids in the second room or fill it with a couple of your favorite people. There’s a comfy spot for whoever’s fortunate enough to be coming along.
Are there vacation rentals with WiFi in Annapolis?
Take your pick of nine vacation rentals with WiFi in Annapolis. If you’d like to disconnect from the world on your trip, but still need to be connected to the internet, these properties are for you. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Annapolis?
Decide on your travel dates and then use the filter tool to locate vacation rentals with ac in Annapolis on Vrbo. With 12 air-conditioned properties to choose from here, you can look forward to a cool and comfortable break.
How old do you have to be to rent a vacation rental in Annapolis?
You’ll need to check with the Annapolis vacation home you want on Vrbo as the age limit varies. However, it’s normally 16, 18 or 21.
How long can I rent a vacation rental in Annapolis for?
The amount of time you can rent an Annapolis vacation home for is up to the property. Simply enter your travel dates to view options offering longer term stays. They come with everything you need to make your extended getaway more comfortable and convenient, like kitchens and backyards. Some properties may also offer weekly or monthly discounted prices, so you can stick around for longer for less.
Does Vrbo offer discounts for vacation homes in Annapolis?
In Annapolis, you’ll find some fantastic discounts and deals for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether you’re planning a weekend escape or a few weeks away, we’ve got plenty of options to suit every kind of traveler.

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