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Annapolis Vacation Rentals
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Vacation Rentals in Annapolis
Annapolis
Stay at this cottage in Annapolis. Enjoy free WiFi, onsite parking, and a garden. Popular attractions Helen Avalynne Tawes Garden and Navy-Marine Corps Memorial ...
10/10 Exceptional! (36 reviews)
Lovely respite close to the Yard
"Two of us came to visit with our Mid while he had a little downtime. Lovely cottage on the water; working felt a little less onerous watching the boats go by. We had everything we needed. Minutes from the Academy but out of the fray. Jim was a gracious host!"
Reviewed on May 26, 2023
Annapolis
The price is $275 per night from Jun 6 to Jun 7
$275
per night
Jun 6 - Jun 7
Stay at this vacation home in Annapolis. Enjoy free WiFi, private pools, and a water park. Popular attractions U.S. Naval Academy Golf Club and Maryland World ...
10/10 Exceptional! (23 reviews)
Perfectly cozy, lovely location!
"Our stay was short, yet wonderful. The RV homes exceeded all of our expectations. It was a joy to be there. Everything was clean, spacious and accommodating! The finer details,m as were also very much appreciated! The area was serene. We’ll definitely be back. Thank you Beth ∧y!"
Reviewed on Apr 23, 2023
Annapolis
Stay at this apartment in Annapolis. Enjoy free WiFi, a sauna, and onsite parking. Popular attractions U.S. Naval Academy Golf Club and Chesapeake Bay Bridge ...
9.2/10 Wonderful! (5 reviews)
Unique property with SPA amenities
"We took advantage of the SPA - heat and tub. The walk-in closet served as a second bedroom for a blowup bed we brought along."
Reviewed on May 23, 2023
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Annapolis
Stay at this houseboat in Annapolis. Enjoy WiFi, onsite parking, and a garden. Popular attractions Annapolis Landing Marina and Annapolis Maritime Museum are ...
9.8/10 Exceptional! (25 reviews)
New Experience!
"Never thought of staying ON the water. Was a little nervous when we first arrived because of the movement but it settled and we had no problem. The only thing missing on the houseboat was a full length mirror. I was looking on the back of doors but couldn’t find one. We so enjoyed going on top and ..."
Reviewed on May 31, 2023
Annapolis
Stay at this family-friendly apartment in Annapolis. Enjoy free WiFi, a water park, and onsite parking. Popular attractions Annapolis Landing Marina and Annapolis ...
10/10 Exceptional! (16 reviews)
Just Awesome!
"Everything was as described and better. We enjoyed the stay and the property is amazing. Thanks Laura!"
Reviewed on May 15, 2023
Annapolis
The price is $295 per night from Jun 6 to Jun 7
$295
per night
Jun 6 - Jun 7
Stay at this apartment in Annapolis. Enjoy free WiFi, private pools, and a water park. Popular attractions U.S. Naval Academy Golf Club and Maryland World War ...
10/10 Exceptional! (53 reviews)
Idyllic VRBO Experience!
"Beth & Captain Andy are the quintessential VRBO Hosts. Communication was excellent, complete, cordial, and fast. Our first visit to Annapolis was spawned by the idea of seeing the US Navy Blue Angels flight demonstration. Well, we had no idea it was graduation week at the Naval Academy; and Beth ..."
Reviewed on May 29, 2023
Annapolis
Stay at this cottage in Annapolis. Enjoy free WiFi, onsite parking, and a garden. Popular attractions Sandy Point State Park and Bay Hills Golf Club are located ...
10/10 Exceptional! (21 reviews)
Nice cottage for 2
"The cottage was well equipped for my partner and I and our small dog. The yard was lovely and peaceful with a firepit. The small park/beachfront area is about a 10 minute walk away, and is calm enough to wade into or even fish. Overall the cottage offered us a relaxing weekend away near the beautiful ..."
Reviewed on May 17, 2023
Annapolis, MD
Stay at this vacation home in Annapolis. Enjoy free WiFi, a garden, and fenced yards. Our guests praise the comfy rooms in our reviews. Popular attractions Chase ...
10/10 Exceptional! (92 reviews)
2023 commissioning week
"Lovely location. Walking distance to DTA. The home was clean and had all the kitchen items necessary to feel at home. I would highly recommend. The owners were very easy to communicate with."
Reviewed on May 31, 2023
Annapolis
Stay at this family-friendly condo in Annapolis. Enjoy private pools, a water park, and WiFi. Popular attractions Ego Alley and Maynard-Burgess House are located ...
9.6/10 Exceptional! (84 reviews)
A short walk to DTA and USNA
"Close by everything we needed - easy access - great views form the apartment - comfortable -"
Reviewed on Apr 16, 2023
Annapolis
Stay at this apartment in Annapolis. Enjoy free WiFi, onsite parking, and a balcony. Popular attractions Westfield Annapolis Mall and Annapolis Mall Shopping ...
9.8/10 Exceptional! (39 reviews)
Lovely Stay!
"We’ve stayed at this property twice now, and it has been very clean and comfortable both times. The owner is very easy to communicate with. Price is reasonable and location is ideal for anyone interested in visiting downtown Annapolis/USNA!"
Reviewed on May 16, 2023
Annapolis
Stay at this family-friendly vacation home in Annapolis. Enjoy free WiFi, onsite parking, and a garden. Popular attractions Bay Ridge Beach and Annapolis Golf ...
9.8/10 Exceptional! (70 reviews)
What a pleasant stay
"I rented this house almost 2 years ago for my mid’s commission week. The Winston couple are the best host of Annapolis I have met in the past 4 years. The house is spotless and has everything we need. We held a postgraduation party and Winston couple helped us to turn it to successful party. What ..."
Reviewed on May 29, 2023
Annapolis
Stay at this vacation home in Annapolis. Enjoy free WiFi, a fitness center, and onsite parking. Popular attractions Spa Creek and Maynard-Burgess House are located ...
8.6/10 Excellent! (9 reviews)
Annapolis Charmer
"I felt very much at home during my stay in this charming house. The bed was comfortable and the shower was great. Friendly neighbors in a nice neighborhood. A great experience."
Reviewed on May 29, 2023
Annapolis, MD
Stay at this vacation home in Annapolis. Enjoy free WiFi, onsite parking, and a garden. Our guests praise the bathrooms and the family amenities in our reviews. ...
9.4/10 Exceptional! (84 reviews)
Wonderful house
"The pictures of this sweet house do not do if justice- it is really so lovely and much larger than it appears. It was the perfect spot for a relaxing mothers day weekend!"
Reviewed on May 15, 2023
Annapolis
Stay at this apartment in Annapolis. Enjoy free WiFi, onsite parking, and barbecue grills. Popular attractions Annapolis Maritime Museum and Annapolis Landing ...
9.6/10 Exceptional! (19 reviews)
Great location
"Property was in a great location. Walkable to many restaurants /bars, 20-25 min walk to downtown Annapolis, 5 min drive, but parking is difficult there. This was perfect for the two of us. My only complaint is that the listing says 1 bedroom, there isn’t a bedroom, the Murphy bed is in the living ..."
Reviewed on May 9, 2023
Annapolis, MD
Stay at this family-friendly vacation home in Annapolis. Enjoy WiFi, onsite parking, and barbecue grills. Popular attractions Bay Ridge Beach and Annapolis Golf ...
10/10 Exceptional! (12 reviews)
A nice family getaway
"Julie is a great host, very thoughtfully arranged property, just perfect for a family stay. Convenient location and enjoyable time. Thank you!"
Reviewed on Apr 21, 2023
Annapolis
Stay at this vacation home in Annapolis. Enjoy free WiFi, a garden, and barbecue grills. Popular attractions Annapolis Maritime Museum and Annapolis Landing ...
9.6/10 Exceptional! (5 reviews)
USNA visit
"Excellent home for a weekend visiting our USNA plebe!"
Reviewed on Oct 21, 2022
Annapolis
Stay at this vacation home in Annapolis. Enjoy free WiFi, a TV, and cable/satellite TV. Popular attractions 48 Fleet Street and The Colonial Players are located ...
9.8/10 Exceptional! (30 reviews)
All around great place!
"The two best things about this house were the location and the living room. We are six women who wanted to spend time catching up and walking. The living room was spacious and the house was walking distance to everything. I would definitely recommend it."
Reviewed on May 16, 2023
Annapolis, MD
Stay at this apartment in Annapolis. Enjoy free WiFi, onsite parking, and a Smart TV. Popular attractions John Smith House and Annapolis City Dock are located ...
9.8/10 Exceptional! (17 reviews)
Anniversary weekend
"Our stay at this rental was a delight from the moment we walked in. It is very nicely appointed which is welcoming to the visitor immediately. It is longer rather than wider but for just the two of us was never an issue and it is actually quite spacious. We also noticed that the place was super clean. ..."
Reviewed on Apr 25, 2023
Annapolis
The price is $245 per night from Jun 5 to Jun 6
$245
per night
Jun 5 - Jun 6
Stay at this family-friendly vacation home in Annapolis. Enjoy free WiFi, private pools, and a water park. Popular attractions U.S. Naval Academy Golf Club and ...
10/10 Exceptional! (20 reviews)
Fun spot in a Great location
"Beth and Andy were so lovely and their area was great! We had chairs set up for us when we got there and they were easy to reach if we needed anything. Will definitely stay again!"
Reviewed on Nov 14, 2022
Annapolis
Stay at this vacation home in Annapolis. Enjoy free WiFi, onsite parking, and a garden. Popular attractions Spa Creek and Annapolis Landing Marina are located ...
10/10 Exceptional! (41 reviews)
All good.
"Nice little house. Super clean. Great location."
Reviewed on May 10, 2023
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
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
Crowne Plaza Annapolis, an IHG Hotel
173 Jennifer Rd, Annapolis, MD, 21401
Fully refundable
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 $117 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
Recent reviews of Annapolis propertiesExpedia verified reviews
Graduate Annapolis
Graduate Annapolis5/5 Excellent"From valet to checkin to housekeeping I passed in a hall, staff were professional, welcoming and congenial. The room was clean, comfortable and I loved the decor. I walked to the US Naval Academy in 15 minutes. I liked the off street vehicle entrance and chose the valet parking vs self for just $4 more. I will stay here again. "A verified traveler stayed at Graduate AnnapolisPosted 1 day ago
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