Annapolis Vacation Rentals

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Vacation Rentals in Annapolis

Directly Across from Gate One & Steps from the Waterfront
Fridge, microwave, oven, stovetop
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (190)
"Great location, easy walk to restaurants, bars, and shopping. Furnishings were comfortable, back patio was lovely and the historic feel was charming. "
Directly Across from Gate One & Steps from the Waterfront
Bay View Studio Apartment
Outdoor spa tub
Bay View Studio Apartment
10.0 out of 10, Exceptional, (32)
"This property was beyond our expectations. Laura was an informative and gracious hostess. The proximity to the Chesapeake Bay was peaceful and inspiring. The cleanliness and decor were exceptional."
Bay View Studio Apartment
Waterfront Annapolis Home: Fire Pit & Fishing Pier
Exterior
Waterfront Annapolis Home: Fire Pit & Fishing Pier
9.2 out of 10, Wonderful, (28)
"I was in town for the great Chesapeake bay swim. The house is in a great location, very close to the bridge and a short drive into town. The house was well equipped, clean, and as described."
Waterfront Annapolis Home: Fire Pit & Fishing Pier
Anchor's Away in the Heart of Eastport!
Fridge, microwave, oven, stovetop
Anchor's Away in the Heart of Eastport!
9.8 out of 10, Exceptional, (33)
"Brief, but great stay. I could walk everywhere I wanted to go (chiefly the US Naval Academy, local restaurants and bars)."
Anchor's Away in the Heart of Eastport!
Cozy place close to the city dock
Beach
Cozy place close to the city dock
10.0 out of 10, Exceptional, (59)
"Perfect! Nathalie was professional, gracious, friendly, and honest. I would definitely recommend her highly."
Cozy place close to the city dock
Annapolis Condominium in the heart of the historic center
Property grounds
Annapolis Condominium in the heart of the historic center
9.8 out of 10, Exceptional, (255)
"My friends and I were looking for a convenient location to enjoy the holiday festivities in Annapolis. Christine’s home was beautiful and just as described!! It was clean and welcoming, located within easy walking distance from the main strip. The home came equipped with basically everything we needed. Christine was super responsive and friendly. Check in/check out was simple. I’d absolutely stay again!"
Annapolis Condominium in the heart of the historic center
Waterfront Oasis of Annapolis Star
Outdoor pool, a heated pool
Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (64)
"I found Beth and Andy’s place because I wanted something different than a hotel stay. This was a business trip but why not enjoy your location? Well relaxing getaway was what I found! The property was so inviting, the hosts were extremely helpful, attentive and very welcoming. I had the apartment on the property and the amenities were great. Having a kitchen to avoid take out is always a bonus. The property was well kept and very clean. The pool and gathering areas very relaxing. The...
The price is $502
includes taxes & fees
$440 per night
Aug 6 - Aug 7
Waterfront Oasis of Annapolis Star
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
9.8 out of 10, Exceptional, (25)
"Our children and granddaughters spent a wonderful time at this lovely home. It was clean, extremely comfortable and the billiard game room was a big hit with our family! It was truly a wonderful home as well as a perfect location for activities, restaurants and shopping. Thank you to our very responsive hosts!"
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
USNA home Downtown Annapolis
Fridge, microwave, oven, stovetop
USNA home Downtown Annapolis
10.0 out of 10, Exceptional, (4)
"Nice relaxing getaway space. It served as a homebase for our vacay to MD/DC. It had all the amenities a family would need. The proximity to Annapolis harbor and access to the highway made staying local or heading to the city easy. The host was prompt and responsive on any question which arose. We were thoroughly satisfied with our experience."
The price is $443
includes taxes & fees
$389 per night
Jul 29 - Jul 30
USNA home Downtown Annapolis
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
Property grounds
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
10.0 out of 10, Exceptional, (65)
"We enjoyed the house and all it offered. The koi pond and food to feed them was really a cool touch."
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
Your Annapolis Adventure Starts Here!!
Fridge, microwave, oven, stovetop
Your Annapolis Adventure Starts Here!!
10.0 out of 10, Exceptional, (127)
"Beautiful property, easy to find located near all the conveniences you could need great communication by property manager (thanks Joie!) really close to beaches, parks, trails, etc. (we went to Sandy point beach and visited the historic mansion & slave plantation property)"
Your Annapolis Adventure Starts Here!!
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Fridge, microwave, oven, stovetop
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
10.0 out of 10, Exceptional, (88)
"We visited during a heat wave; as expected, the pool was a blessing. The pool was also way bigger than the photos could possibly capture. What an absolute joy. Liz was clear, helpful, and took great pride/care in her property. Legit oasis. We hope to visit again."
The price is $717
includes taxes & fees
$629 per night
Aug 19 - Aug 20
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
Fridge, microwave, oven, stovetop
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
9.6 out of 10, Exceptional, (101)
"Great spot if your kids get a chance to do a a day program USNA sports camp! Thank you!"
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
9.8 out of 10, Exceptional, (7)
"Turning Point on the Little Magothy was perfect for our family weekend! We’re local, but we wanted a place with a pool to come together with my siblings, their spouses and their kids, and this was great! Every couple had their own bedroom with a king bed, which was awesome! The kids had their own twin bunk beds, which they loved. There was enough space for the 12 of us to have dinner together at the dining table, and to hang out in the living room. The home was beautiful, and we were very happy...
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Amazing views, short walks to great dining!
View from property
Amazing views, short walks to great dining!
10.0 out of 10, Exceptional, (69)
"Jim is an exceptional host who goes above and beyond to create an unparalleled experience with outstanding service and hospitality. We've stayed in numerous rentals, but this one truly stands out. The waterview, the boats, the hospitality, and the prime location were all incredible and deeply appreciated. If you're on the fence about booking this place, just do it. It's perfect for a couple. I even caught some nice perch right off the dock! Our biggest concern about renting on the water was the...
Amazing views, short walks to great dining!
Cozy 1st Floor King George one bedroom apartment right across from USNA
Fridge, microwave, oven, stovetop
Cozy 1st Floor King George one bedroom apartment right across from USNA
10.0 out of 10, Exceptional, (21)
"Clean. Great location. Adorable inside…so much original charm but not outdated and a well-stocked kitchen (which we didn’t use but I made note of it for future visits!). Julie was quick to answer all my questions."
The price is $345
includes taxes & fees
$303 per night
Jul 29 - Jul 30
Cozy 1st Floor King George one bedroom apartment right across from USNA
7 mins away from Downtown Annapolis
Property grounds
7 mins away from Downtown Annapolis
9.8 out of 10, Exceptional, (8)
"Very clean property. Host was wonderful, very communicative and answered all our questions. nice ammenities. clean home. bed linens and beds were very comfortable."
7 mins away from Downtown Annapolis
Charming Annapolis WaterVIEW Home
Property grounds
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (45)
"Beautiful home! Close to Annapolis. Comfortable, large home. Many stairs, so better for family w kids over 5 years. Owner very responsive. Relaxing balconies with swings. Quiet neighborhood!"
The price is $766
includes taxes & fees
$672 per night
Jul 30 - Jul 31
Charming Annapolis WaterVIEW Home
Indulge or be still near Naval Academy/ Annapolis
Beach
Indulge or be still near Naval Academy/ Annapolis
9.4 out of 10, Exceptional, (11)
"Stayed a week while our son sailed at the Naval Academy. Easy 10 minute ride to the city docks. Nice bed and good linens with kitchenette made the stay very comfy Would stay again"
Indulge or be still near Naval Academy/ Annapolis
Charming garden row home, easy 4 block walk to the heart of Annapolis.
Property grounds
Charming garden row home, easy 4 block walk to the heart of Annapolis.
10.0 out of 10, Exceptional, (103)
"Great house! Perfect location. The only negative is that the shower is difficult to get into. If you have a disabled or elderly person, this is a challenge."
Charming garden row home, easy 4 block walk to the heart of Annapolis.
Don't see what you're looking for?
See all available properties in Annapolis
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Annapolis you may be interested in

Historic Inns of Annapolis
Exterior
Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, (1646)
"Excellent stay except for a couple minor issues. Told to use the OpenKey app to check in but was not available until after physical check in at the front desk. Since the building was separated it was a little more than a short walk to our building. The app would allow us to go straight to the room. Understood the room was in a historic building and had some quirks but the short step up to the bathroom was a trip hazard. Maybe mark it so it doesn’t blend into the carpet. Otherwise a really great...
The price is $227
includes taxes & fees
$179 per night
Jul 28 - Jul 29
Historic Inns of Annapolis
Crowne Plaza Annapolis, an IHG Hotel
Pool
Crowne Plaza Annapolis, an IHG Hotel
3.5 star property
8.8 out of 10, Excellent, (1001)
"Makeovers used in bathroom to update their condition are very shoddy."
The price is $118
includes taxes & fees
$103 per night
Aug 11 - Aug 12
Crowne Plaza Annapolis, an IHG Hotel
Graduate Annapolis
View from property
Graduate Annapolis
4.0 star property
9.4 out of 10, Exceptional, (1006)
"When we are visiting Annapolis the Graduate is our favorite place to stay. The staff is friendly and welcoming! You can’t beat the location, walking distance to downtown. There is a restaurant on site with plenty of options, check out the schedule for live music also. The guest rooms have plenty of space and the beds are comfortable. "
The price is $193
includes taxes & fees
$169 per night
Aug 18 - Aug 19
Graduate Annapolis
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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 $345 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

Are there vacation rentals in Annapolis?

Yes, there are vacation rentals in Annapolis near Annapolis Maritime Museum, 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?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: Visitors like this Annapolis vacation home rental. It offers a balcony, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the spa tub in this rental home to help you unwind. Some other top choices in Annapolis are 421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking! and Recently Renovated Annapolis Home - Conveniently Located.

How many vacation rentals will I find in Annapolis?

Expedia has 418 vacation rentals for your stay in Annapolis.

What can I see and do in Annapolis?

Enjoy the outdoors at Maryland Quiet Waters Park and Sandy Point State Park, or simply take in cultural attractions like Maryland Hall for Creative Arts 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.

Recent reviews of Annapolis properties
Expedia verified reviews

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

5/5 Excellent
Clean, comfortable and pleasant staff
"Clean, comfortable, pleasant staff, and hot breakfast. Only complaint would be the cost of water and drinks in the lobby, not sure why hotels feel the need to take advantage of pricing on these things if you forgot to stop and get waters or want a snack. "
A verified traveler stayed at SpringHill Suites by Marriott Annapolis
Posted 18 hours ago
SpringHill Suites by Marriott Annapolis