Annapolis Vacation Rentals from $199: Search Short-Term Rentals

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Vacation Rentals in Annapolis

Annapolis Vacation Rental Travel Info

Popular accommodation	Annapolis private vacation homes
Known landmarks	Hauser Bridge, Kruse Rhododendron State Natural Reserve and Fisk Mill Cove
International airport	Oakland, CA (OAK-Oakland Intl.)

Other types of properties in Annapolis you may be interested in

"Amazing property, I loved going there for a staycation. Just wanted to relax and enjoy some time with my husband for our anniversary. Calm and quiet, with great staff. Will be back"

$354 total

includes taxes & fees

Jun 4 - Jun 5

"This wasn't a super fancy resort but a very cut motel.The rooms were clean, beds comfortable, and the shower had great water pressure. They lady doing our check in was super friendly:) "

$177 total

includes taxes & fees

Jun 24 - Jun 25

"Best dog friendly place!! We always stay here when we go wine tasting and need to bring the dogs. It’s close to Healdsburg and all the wineries on dry creek road. It always clean and easy after hours check in. Cute pool area too! "

$150 total

includes taxes & fees

Jun 4 - Jun 5

Everything you need to know about Annapolis vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Annapolis vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Annapolis vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Annapolis vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Annapolis. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Annapolis in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $199 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Annapolis rentals

At Expedia, we put the best Annapolis vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Annapolis rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Annapolis vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Annapolis. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Annapolis?

Yes, you can find vacation rentals near popular local attractions in Annapolis, or you can select a more remote option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals in Annapolis?

Sunny Home. Hot Tub. Walk to 2 Beaches, Rec Center, Bluff Trail and the Lodge.: This vacation home rental near Annapolis is located near the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a garden, a spa tub, and a selection of books so you can immerse yourself in your vacation.

What’s there to see and do in Annapolis?

While you're exploring the area, Gualala River and Pebble Beach are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Black Point Beach and Walk On Beach.

What’s a vacation rental in Annapolis like?

Vacation rentals are privately owned properties you can book for a long or short time in Annapolis. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for small groups.

Recent reviews of Annapolis properties
Expedia verified reviews

5/5 Excellent

"I very much enjoyed meeting interacting with Marilyn.Not only did she check I wife and I in but she oriented his to the area and gave his dinner recommendations. Old-fashioned hospitality was nice to experience."

A verified traveler from Laguna Niguel stayed at Geyserville Inn

Posted 12 hours ago