Annapolis Vacation Rentals from $450: Search Short-Term Rentals

Q: What's the top vacation rental in Annapolis?

Charming Annapolis WaterVIEW Home : Visitors like this Annapolis vacation home rental. It is located on the waterfront and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub. Some other top choices in Annapolis are Private Cottage on gated estate and Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach .

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In two weeks

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Our top choices for Annapolis vacation rentals

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Annapolis

William

Waterfront Oasis of Annapolis Star

Annapolis

Thomas

$404 nightly

Jun 1 - Jun 2

Total with taxes and fees

Beach nearby, sun loungers, beach towels

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Arundel on the Bay

Henry P.

$601 nightly

Jun 2 - Jun 3

Total with taxes and fees

Charming Annapolis WaterVIEW Home

Arundel on the Bay

Kathy S.

$514 nightly

Jun 8 - Jun 9

Total with taxes and fees

Cute bungalow blocks to Stadium

Admiral Heights

Holly W.

$467 nightly

Jun 8 - Jun 9

Total with taxes and fees

Cozy 2br home w/ parking in downtown Annapolis

Historic District

Sophie P.

$395 nightly

Jun 1 - Jun 2

Total with taxes and fees

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Annapolis

$589 nightly

Jun 7 - Jun 8

Total with taxes and fees

Pool Loft Suite | Bay Access & Beach Passes

Cape Saint Claire

Ana S.

$424 nightly

May 28 - May 29

Total with taxes and fees

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Top Annapolis Hotel Reviews

Crowne Plaza Annapolis by IHG

10/10 Excellent

"Ibrahim who worked th front desk ws great."

The Westin Annapolis

8/10 Good

"The staff was so welcoming and friendly. So helpful. Valet parking very efficient. Rooms, lovely, beds extremely comfortable. The only thing was the breakfast was no so great. I got the American Breakfast. Eggs cooked wrong and the ham was like shoe leather. I couldn’t even cut it with a knife. They brought me sausage as a substitute and that was worse. Bread was cheap. Location great!"

Historic Inns of Annapolis

6/10 Okay

"Well, the Inn is centrally located but it needs work in several areas. When we checked in, the valet said leave your bags in the car in case you are not staying here. So I went in but left my ID in the car and the desk told me to bring by ID and bags in to get registered. Which I did, and then was told to bring my bags back to the car and drive to another inn! We drove to the other Inn (Maryland house) and found some 15 minute loading zone, and ultimately found an entrance on our third try. There is no handicapped entrance FYI. Our room had charm, a window air conditioner that was adequate, and a coffee maker with 2 small bottles of water. The bathroom was so tiny, and the shower was the size of an old telephone booth. (My wife needed the shower cap because she could not avoid the shower head.) Our room was made up very late each day, possibly at 3:00-4:00. The 2 small water bottles were never replaced. The TV was as low def as possible, could not read the score or see the puck, etc. Anyway, centrally located, but they could improve."

Country Inn & Suites by Radisson, Annapolis, MD

8/10 Good

"The hotel in general needs updating badly. Carpet seems dirty in the room and in the general area. Mold in the bathroom on the ceiling in shower area and above the door frame. AC unit is loud while running and elevator broke down just before we arrived for a few days. Luckily, we had only one flight to go up and my family didn't mind the walk. Breakfast was good and Staff was super Nice. Complimentary 24hr coffee and teas was a treat. And of course, those freshly baked cookies were something to look forward for."

SpringHill Suites by Marriott Annapolis

6/10 Okay

"Carpet was old and needed replacement and cleaning. Quite smelly Once I mentioned to the front desk, they got maintenance on it and reported it to corporate. Needs some updates. Could not use the gym or pool area Gym smelled bad not cleaned though lots of housekeeping around and the pool water was and hot tub were merky. It was also insane that they were charging for unsecured parking that used to be free."

Graduate by Hilton Annapolis

6/10 Okay

"We had a reservation for a king atrium room. When we checked in they said that room wasn’t ready but a two queen room was instead. It was implied the room was nicer and cost more. Instead of an atrium view we got a rooftop/parking lot view and a handicap room. The shower was extremely difficult to use without flooding the bathroom. Staff wasn’t interested in helping. The beds were extremely low and about two feet off the ground. No bathroom counter space as I had booked because the space was designed to accommodate a wheelchair. The closet was not usable because the rod was extremely low so someone in a wheelchair could reach it. But, the rod was just above the wall mounted safe so nothing could hang from it. Not a great experience for a very expensive stay."

Find out more about Annapolis

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 $450 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.

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Frequently asked questions

Are there vacation rentals in Annapolis?

Yes, there are vacation rentals in Annapolis near Maryland Hall for Creative Arts, or you can choose a secluded option if you're looking for extra privacy while you relax. Tourists who visit Annapolis speak highly of the college campus and array of shops. While you're in the area, you can also enjoy the top-notch restaurants and marina.

What's the top vacation rental in Annapolis?

Charming Annapolis WaterVIEW Home: Visitors like this Annapolis vacation home rental. It is located on the waterfront and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub. Some other top choices in Annapolis are Private Cottage on gated estate and Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach.

How many vacation rentals will I find in Annapolis?

Expedia has 388 vacation rentals for your stay in Annapolis.

What can I see and do in Annapolis?

Enjoy the outdoors at Carrs Beach and Maryland Quiet Waters Park, or simply take in cultural attractions like Hammond-Harwood House and Annapolis Maritime Museum. While here, Maryland State House and William Paca House are other places worth a visit.

What are vacation rentals like in Annapolis?

Vacation rentals are privately owned properties you can stay in for a short or long stay in Annapolis. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion 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 an attractive option for families.

Annapolis Vacation Rentals

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Our top choices for Annapolis vacation rentals

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Waterfront Oasis of Annapolis Star

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Annapolis WaterVIEW Home

Cute bungalow blocks to Stadium

Cozy 2br home w/ parking in downtown Annapolis

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Pool Loft Suite | Bay Access & Beach Passes

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!

Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.

Sailboat Experience in Annapolis

Mins to DTA - King Beds - Parking

Chapel Gate 3BR Steps to City Dock & Naval Academy

Fabulous 5-bedroom house with AC in charming Annapolis

Historic Row Home in Downtown Annapolis

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Top Annapolis Hotel Reviews

Crowne Plaza Annapolis by IHG

Find out more about Annapolis

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