Annapolis vacation rentals

We found 263 vacation rentals — enter your dates for availability

Scroll through and select from vacation rentals in Annapolis to find one that's perfect for your trip. Vacation homes offer the best amenities for your family, friends, or furry companion, such as parking and a fireplace. At the end of the day, you'll be sure to find a rental that has what everyone needs, including accessible or non-smoking choices.
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Find out more about Annapolis

Find out more about Annapolis

Why visit Annapolis

  • Scenic outdoor adventures: Enjoy beautiful beaches, state parks, and winding rivers perfect for hiking, kayaking, and relaxing.
  • Charming downtown: Explore vibrant local shops and eateries that capture the essence of Annapolis’ friendly atmosphere.
  • Diverse accommodation options: Choose from cozy cottages, private homes, and rustic cabins for a comfortable stay.
  • Family-friendly activities: Find a variety of activities suitable for all ages, ensuring fun for everyone.
  • Tranquil neighborhoods: Discover secluded spots and scenic views that invite relaxation and exploration.

Popular types of accommodation in Annapolis

Discover the charm of Annapolis with a variety of vacation rentals to suit your needs. Whether you prefer houses, cozy cottages, or rustic cabins, there’s the perfect spot for you. Our selection includes vacation apartments and house rentals, ensuring a comfortable stay for families and friends alike. Explore the best vacation properties in the United States and enjoy a memorable getaway in the historic heart of Maryland.

  • Houses: The top choice for visitors to Annapolis, these homes offer a spacious and personalized experience for families, couples, or groups.
  • Cottages: A close second, these quaint and cozy accommodations provide a charming atmosphere for a relaxing getaway.
  • Cabins: Ideal for nature enthusiasts, cabins offer a rustic escape surrounded by the beauty of the outdoors.
  • Apartments: Perfect for those seeking convenience, apartments deliver a home-like feel with easy access to local attractions.
  • Villas: Providing luxury and ample space, villas are a fabulous option for travelers looking for an upscale experience.**

Top attractions near Annapolis

Annapolis, California, is a fantastic destination for outdoor enthusiasts and adventure seekers. With beautiful beaches, scenic state parks, and winding rivers, visitors can enjoy a variety of activities that cater to both cultural exploration and outdoor experiences. Whether you're looking for relaxation by the beach or thrilling adventures in nature, Annapolis offers a range of vacation ideas to ensure a memorable getaway.

  • Pebble Beach: A picturesque beach offering stunning coastal views and a relaxing atmosphere. Perfect for sunbathing, beachcombing, and enjoying the soothing sound of waves, Pebble Beach is an ideal spot to unwind and soak up the sun.
  • Gualala River: This scenic river is surrounded by lush landscapes, providing opportunities for kayaking, fishing, and wildlife observation. With its serene environment, Gualala River is perfect for outdoor enthusiasts seeking adventure and natural beauty.
  • Galleons Point: A family-friendly park featuring trails and picnic areas, Galleons Point is an eco-friendly destination. Enjoy outdoor activities while taking in the beautiful surroundings, making it a great spot for a day out with loved ones.

Things to do recommended for couples

For a romantic getaway in Annapolis, visit Flowers Vineyard and Winery, just 14 miles away, or head to Maple Creek Winery and Yorkville Cellars, both 15 miles from town. Enjoy the beautiful landscapes and intimate atmospheres perfect for couples seeking a memorable experience.

Things to do recommended for families

Families will love the natural beauty of Gualala Point Regional Park, located 9 miles from Annapolis. This recreational area offers serene spots for relaxation, hiking trails, and stunning coastal views, making it a perfect destination for outdoor fun and quality time together.

Things to do recommended for groups

Groups visiting Annapolis can enjoy a round of golf at Sea Ranch Golf Links, hike the scenic Gualala Bluff Trail, and unwind with craft brews at Anderson Valley Brewery Company, creating memorable experiences filled with outdoor adventure and relaxation.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're traveling with a group, family, pets, or planning an extended stay, it's important to prioritize your filters accordingly. Here are some helpful booking tips for using Vrbo.

  • Traveling to Annapolis with a group: Think about how many bedrooms you'll require, as well as additional features like a full kitchen or outdoor space for group gatherings. The good news is that you can easily filter for these options and more on Vrbo.
  • Traveling to Annapolis with young kids: Traveling with little ones can be quite a task. It's important to prioritize their comfort and safety, as well as look for suitable amenities, like a private swimming pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Annapolis: For many, a family vacation isn’t truly complete without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Many of these 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 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 rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Annapolis

Discover the charm of Annapolis, California, a quaint village perfect for outdoor adventures and scenic getaways. Explore nearby neighborhoods, each offering a friendly atmosphere and beautiful views. Enjoy family-friendly activities and secluded spots that invite relaxation. Don’t miss the vibrant downtown Annapolis, where local shops and eateries await. With nearby destinations just a short drive away, your vacation promises a delightful blend of adventure and tranquility.

  • Sea Ranch: Located a mere 5 miles from Annapolis, Sea Ranch is a picturesque coastal community that draws visitors seeking outdoor adventures and stunning scenery. The area is renowned for its breathtaking beaches and access to the nearby national state park, where you can hike along scenic trails or simply relax by the serene river. Golf enthusiasts will appreciate the local golf course, which offers a challenging game with beautiful views. Whether you're exploring the rugged coastline or enjoying a peaceful day in nature, Sea Ranch promises an unforgettable experience.
  • Gualala: Situated 10 miles from Annapolis, Gualala is a charming coastal town perfect for those who love the great outdoors. The town is surrounded by beautiful landscapes, including beaches and lush national state parks. With an abundance of hiking trails and recreational areas, adventure seekers will find plenty to do. Gualala's vibrant arts scene, local shops, and stunning river views make it a great spot to unwind and take in the natural beauty of California's coastline.
  • Stewarts Point: Just 5 miles from Annapolis, Stewarts Point is a hidden gem that offers a blend of outdoor activities and scenic beauty. This quaint city is perfect for those looking to immerse themselves in nature, with access to recreational areas and stunning golf courses. Visitors can also enjoy body treatment services for a relaxing experience after a day of exploration. With its proximity to beautiful beaches, national state parks, and the tranquil river, Stewarts Point is a must-visit for nature lovers and adventure seekers alike.

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 months are July and July. Peak season runs in June, June to July, July to August and August, while off-peak times, like January to February, February, December to January and December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January47.7°F (8.7°C)Light RainMostly SunnyModerately LowSlightly Low
January47.7°F (8.7°C)Light RainMostly SunnyModerately LowSlightly Low
February48.4°F (9.1°C)Light RainMostly SunnyModerately LowSlightly Low
February48.4°F (9.1°C)Light RainMostly SunnyModerately LowSlightly Low
March49.8°F (9.9°C)Light RainMostly SunnyAverageSlightly Low
March49.8°F (9.9°C)Light RainMostly SunnyAverageSlightly Low
April54.1°F (12.3°C)No Rain (Dry)Mostly SunnyAverageAverage
April54.1°F (12.3°C)No Rain (Dry)Mostly SunnyAverageAverage
May59.4°F (15.2°C)No Rain (Dry)SunnyAverageAverage
May59.4°F (15.2°C)No Rain (Dry)SunnyAverageAverage
June66.4°F (19.1°C)No Rain (Dry)SunnyModerately HighSlightly High
June66.4°F (19.1°C)No Rain (Dry)SunnyModerately HighSlightly High
July70.2°F (21.2°C)No Rain (Dry)SunnyModerately HighSlightly High
July70.2°F (21.2°C)No Rain (Dry)SunnyModerately HighSlightly High
August69.8°F (21.0°C)No Rain (Dry)SunnyModerately HighSlightly High
August69.8°F (21.0°C)No Rain (Dry)SunnyModerately HighSlightly High
September67.3°F (19.6°C)No Rain (Dry)SunnyAverageAverage
September67.3°F (19.6°C)No Rain (Dry)SunnyAverageAverage
October61.0°F (16.1°C)Light RainSunnyAverageAverage
October61.0°F (16.1°C)Light RainSunnyAverageAverage
November52.0°F (11.1°C)Light RainMostly SunnyAverageAverage
November52.0°F (11.1°C)Light RainMostly SunnyAverageAverage
December46.8°F (8.2°C)Light RainMostly SunnyModerately LowAverage
December46.8°F (8.2°C)Light RainMostly SunnyModerately LowAverage

Booking with Vrbo is simple

Are you hoping to cut costs on your upcoming trip? Being flexible with your travel dates can really pay off, as prices can vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your reservation. Being the planner has its perks. By enrolling in our travel rewards program, One Key, you can immediately access exclusive member savings and earn OneKeyCash on eligible bookings. Sign up today and begin reaping the rewards.

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a convenient way to plan new trips, pick up where you last stopped, or organize your travel plans. You can easily find the properties you’ve saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Choose a vacation rental for your Annapolis getaway

Experience the unique character of Annapolis with a stay in a vacation home rental. You'll find plenty to explore during your stay in the area. If you're looking for accommodations with space to entertain friends and family, Vrbo has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in and around Annapolis

Are you hoping to find attractions to visit in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Annapolis a one-of-a-kind vacation spot. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • Sea Ranch Golf Links (8.3 mi / 13.4 km)
  • Fort Ross Vineyard (17.5 mi / 28.2 km)
  • Flowers Vineyard and Winery (13.7 mi / 22.1 km)
  • Maple Creek Winery (14.8 mi / 23.8 km)
  • Yorkville Cellars (14.8 mi / 23.9 km)
  • Albertina Wine Cellar (19.2 mi / 30.8 km)

Exploring the natural features in Annapolis

Whether you're an active traveler or just want to spend some time taking in the scenery, Annapolis is a great spot to appreciate mother nature. These are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city center:

  • Pebble Beach (4.2 mi / 6.7 km)
  • Black Point Beach (4.3 mi / 6.9 km)
  • Gualala River (6 mi / 9.7 km)
  • Ocean Cove (11.8 mi / 19 km)
  • Stillwater Cove Regional Park (12.6 mi / 20.3 km)
  • Lake Sonoma (18.7 mi / 30.1 km)

Traveling to and around Annapolis

The nearest airport is in Santa Rosa, CA (STS-Sonoma County), located 33.6 mi (54.1 km) from the city center.

Frequently asked questions

What is the best area to stay in Annapolis when booking a vacation rental?
When considering a vacation rental in Annapolis, California, a popular area to stay is along the scenic coastline near the village center. This charming area offers a unique blend of natural beauty and local culture, making it an ideal base for your getaway. You'll find a variety of vacation rentals, ranging from cozy cottages to modern homes, with many offering stunning views of the water.

Being in this area provides easy access to top attractions such as the nearby Point Reyes National Seashore, where you can explore hiking trails, pristine beaches, and breathtaking vistas. Additionally, the historic Tomales Bay area is just a short distance away, superb for kayaking or enjoying fresh oysters at local eateries.

Another appealing option is to stay a little further inland, where you'll experience a quieter, more rustic atmosphere, yet still have quick access to the vibrant coastal attractions.
How much does it cost to rent a vacation home in Annapolis?
Prices for vacation 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 vacation 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.
Can I find long-stay vacation rentals in Annapolis?
A long-stay vacation rental in Annapolis is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there any Annapolis vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Annapolis with parking available—perfect for families or travelers 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.
How early should I book a Annapolis vacation rental?
Book your Annapolis vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Annapolis home rental booking on Vrbo?
To find Annapolis vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy 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 vacation 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.

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