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Compare 899 Vacation Homes in Crownsville with updated reviews, rates, and availability.

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

10.0 out of 10, Exceptional, (73)
"House is exceptionally clean. Hosts are very responsive to questions. House is very well supplied and convenient to most of Annapolis. House is as advertised. "
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

Rooftop Deck Escape! Free Parking!

9.0 out of 10, Wonderful, (23)
"Good location, close to Light Street. House was nice, enjoyed the rooftop deck with fire table. "
The price is AED 419
AED 1,027 total
includes taxes & fees
12 Jan - 13 Jan
Rooftop Deck Escape! Free Parking!

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (38)
"This home was perfect for our 12-person family. There was plenty of room to spread out, and the house was well stocked with everything we needed. It would be a great place to vacation in the summer as well. The owner was helpful, communicated well, and accommodating. We hope we can return sometime in the future."
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Gorgeous Upscale 4 Level Modern 4BR Home + Parking

2.0 star property
10.0 out of 10, Exceptional, (4)
"The house was as described and better. Our host was thoughtful and responsive, and we hope to do it again."
Gorgeous Upscale 4 Level Modern 4BR Home + Parking

Historic Rowe House 2br 2.5ba Cityscape View 2 Bedroom Home by RedAwning

3.0 star property
Historic Rowe House 2br 2.5ba Cityscape View 2 Bedroom Home by RedAwning

Brand New Spacious Luxury Home

10.0 out of 10, Exceptional, (3)
"From communication to check-in and cleanliness, this VRBO has plenty of room and modern amenities. What put this over the top was that a party member left the wallet at the VRBO, and the renters went and retrieved the wallet and met us to return it. They went above and beyond to help us. It has a good backyard and can park 3-4 cars in the driveway; this VRBO has everything. Easily five stars"
Brand New Spacious Luxury Home

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (206)
"A great experience all around"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Cozy 2/1.5 Getaway in Lily Ponds

8.2 out of 10, Very Good, (13)
"I would recommend this house. It’s clean and peaceful. No complaints. The metro station is about a 15 min walk."
The price is AED 209
AED 885 total
includes taxes & fees
14 Jan - 15 Jan
Cozy 2/1.5 Getaway in Lily Ponds

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

10.0 out of 10, Exceptional, (46)
"We had a wonderful time. The home is absolutely fabulous! We are already talking about when we can return. Peaceful and restorative, just what we needed. "
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

Freshly renovated 3-story home 1 block from USNA!

10.0 out of 10, Exceptional, (28)
"What a fantastic location, central to everything in the city. Parked the car and walked everywhere. The house is perfect!!"
The price is AED 544
AED 2,342 total
includes taxes & fees
12 Jan - 13 Jan
Freshly renovated 3-story home 1 block from USNA!

Private Waterfront Woods | Dock, Kayaks, Views

9.6 out of 10, Exceptional, (18)
"This property worked well for our large family. Most houses that sleep larger numbers don't come with a kitchen stocked for corresponding large numbers. But this kitchen was very well stocked with plenty of dishes and larger pots/pans for larger groups. "
Private Waterfront Woods | Dock, Kayaks, Views

Hilltop Hideaway in DC

9.2 out of 10, Wonderful, (5)
"The home was clean and beautiful"
Hilltop Hideaway in DC

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

9.8 out of 10, Exceptional, (62)
"Perfect location. Close to the big cities but far enough away to relax. Lots of shopping close by. Very clean. Trent is an excellent communicator. We highly recommend and will definitely consider staying here again in the future. We picked it because I grew up in Crofton and my mom lives close by. "
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

10.0 out of 10, Exceptional, (21)
"Lovely, quiet and comfortable home not far from route 50, nearby shopping, close to a wonderful Italian restaurant in Stevensville, and 20 minute drive to Annapolis. Owner was very responsive with a few questions we had during our stay. We would definitely stay again. "
The price is AED 189
AED 815 total
includes taxes & fees
13 Jan - 14 Jan
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

10.0 out of 10, Exceptional, (14)
"Everything about this property was first class! We had an amazing stay in this comfortable home! Fully stocked kitchen. Body wash and shampoo in each bathroom. All the details covered. The location is awesome. Quick walk to downtown and the Naval Academy. The host was very accommodating and responsive. Can’t wait to stay again!"
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

House on the Gwynns Falls

8.6 out of 10, Excellent, (7)
"Mary's home is lovely! She is welcoming and kind and the check-in process is simple. I would stay at the home in the future."
The price is AED 621
AED 810 total
includes taxes & fees
15 Jan - 16 Jan
House on the Gwynns Falls

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (23)
"Fifteen ladies from my church stayed at this Vrbo for a weekend conference in Annapolis. We enjoyed the property and the house! We had a beautiful weekend and even got on the water, played pickle ball, and enjoyed the views. The house is beautiful! The kitchen is well stocked and the house is comfortable and there is plenty of parking. Since it was November, the heated sunroom floors were a wonderful bonus. Thank you for the memories and a wonderful stay!"
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (33)
"Perfect for our weekend stay. Checkin was easy and communication with the owner was great! Definitely would stay again. Kentmoor restaurant was awesome. Filled with locals who were friendly and welcoming! Food was great!"
The price is AED 189
AED 812 total
includes taxes & fees
12 Jan - 13 Jan
Relax on Kent Island in 3 Bedroom Home w/Waterview

Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented.

9.4 out of 10, Exceptional, (29)
"This VRBO is in a great neighborhood down by Baltimore's harbor, close to trendy Fells Point. Walking distance to everything. The home is quite large and was in excellent shape. Ray was a very accommodating host. Communication with him was great, and we had no complaints."
Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented.

Whimsical Washingtonian

8.6 out of 10, Excellent, (4)
"We enjoyed our weeklong vacation during Spring Break. This home was very clean. The owner is incredibly prompt to respond and communicate. There could be more kitchen utensils and dishware for guest use. The neighborhood did not instill a sense of security for us. Local neighbors were yelling at all hours, and we did not feel safe to walk to the Benning Rd metro stop. Instead, we drove to the Capitol Heights stop, as we could use the Park and Ride lot there."
Whimsical Washingtonian
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.
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Other property types in Crownsville

Still available for CW 2025 Waterfront dog-friendly Private Pier, Game Room at Jolly Roger

10.0 out of 10, Exceptional, (31)
"Great house for the family to get together. Plenty of toys and things to do on the property. Sitting on the deck as the sun went down was a big hit."
Still available for CW 2025 Waterfront dog-friendly Private Pier, Game Room at Jolly Roger

WhyHotel by Placemakr Columbia

4.0 star property
9.0 out of 10, Wonderful, (601)
"Location, lovely lights and skating rink"
The price is AED 426
AED 481 total
includes taxes & fees
23 Jan - 24 Jan
WhyHotel by Placemakr Columbia

Quaint 3/2.5 home in Fort Dupont

8.0 out of 10, Very Good, (14)
"Clean NO BUGS. Neighborhood quiet. Close to food places for door dash & everything was nice so my stay was awesome! "
The price is AED 283
AED 962 total
includes taxes & fees
13 Jan - 14 Jan
Quaint 3/2.5 home in Fort Dupont
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.