
Cottage holiday rentals in Calvert County
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Top-rated cottage rentals in Calvert County
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Popular amenities for Calvert County cottage rentals
Cottage rentals with a hot tub

Waterfront cottage w/hot tub/ gated/ pier/ firepit
Nice house, very secluded, lots of entertaining space, hot tub was great, back patio, fire pit, everything was great. Isaac was very communicative with all aspects of our stay. An excellent getaway.

Waterfront Cottage, Pier, Sunsets, Hot Tub,Kayaks
Natalie was a wonderful host - the cottage was clean and welcoming and looked just like the photos. Natalie was very responsive, flexible and friendly. The river was peaceful and we enjoyed kayaking and fishing off the dock. We are very thankful we found such a perfect spot for our weekend trip to Maryland.

Cottage on Solitude Creek, Hot Tub, Pool & Firepit
This is our second time visiting and a perfect spot with everything we needed. Could provide more dish towels, paper towels, and trash bags but supplies were provided quickly upon request.

Nautical Vibe Walk 2 Harbor Pubs USNA
Overall a great place. It's only a short 10-15 minute walk on sidewalks to the rest of Eastport and the Annapolis harbor area, but in a quiet neighborhood that isn't busy with vehicle or foot traffic so it was easy to enjoy the lovely garden and patio outside with minimal city noise. It is accurate as described and from the photos. Did not experience any problems in the neighborhood or feel unsafe.

Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
I book this place for my bday I just wanted to have fun & have a break from routine but at the same time feel comfortable like home, and that’s how it was and better we all had a great time. Really nice property, fabulous decoration, great surroundings to visit, and nice backyard to relax and enjoy. The jacuzzi and fire pit unforgettable part of the trip, really nice atmosphere. If there was an issue super easy and efficient way to respond to the situation. Made my bday really special for me and my family <3

Lakefront/Dock, Cove, Boats, HotTub, Woods & Beach
Genuinely one of the most pristine and peaceful places I’ve ever been at a great time, weather with family or friends
Pet-friendly cottage rentals

The Little Anchor Cottage, St. Michaels, MD
Great home in a beautiful area. Spacious rooms and the whole house is equipped with everything you need. I love Airbnbs that feel homey and not ‘commercial’. The area is BEAUTIFUL and walkable with great restaurants near by (checkout limonchello and get the pizza!). Perfect for a weekend.

Perfect St. Michaels Getaway
This cottage was a gorgeous place to relax with my wife for her birthday. The proximity to the bay cannot be beat - especially since she made kayaks available for our stay. I would happily re-book next time I am in the area.

Relaxing Water Views - Mill Creek Cottage
The listing first reported that the home is typically booked -- I now believe it probably would have been had it not been for sheer good fortune. The location on the water in the private-like inlet called Mill Creek adjacent to the Severn river near Annapolis Harbor and the Naval Academy was perfect. Though close to so many things -- including hearing bugles played in the evening and morning from the Academy -- it was also peaceful and calming. Michael was responsive within minutes of my texts and even accommodated an extra day's stay. Every possible amenity was available from add'l drinking water to makeup remover. All was clean and even the bedding in a humid environment was pristine. Remote controls were labeled and extra batteries in the pantry. Lots of Keurig pods. With easy evening bird watching on the side porch after working during the day on fast wireless internet, we were spoiled in this idyllic house. We will soon return with our spouses for more retreats!

Bayside Cottage- In the Town with views
We thoroughly enjoyed our stay at this AIRBNB. It was walking distance to a nice Mexican Restaurant as well as to a brewery. We spent hours on the front porch in the nice rocking chairs. The back of the property overlooked the water which was beautiful! It was close to everything in town! The house was clean and had all of the necessities. We also enjoyed the front sitting area during the morning. The owner was responsive and helpful! We would definitely recommend this property.

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
Shawn's place is great! It is well-cared for and has everything you need to enjoy the indoors and the outdoors. The views of the water are beautiful and you can spend a lot of time watching the different birds. Getting there is easy and not far from restaurants and grocery stores. Shawn makes you feel special and wants to ensure you have a wonderful stay. Hope to go back soon.

Secluded Cottage_ A+ Amenities in Historic Dwntwn
Perfectly located, walked everywhere. Clean and comfortable.

Rockhold Creek Cottage
We stayed at Richard's house for 3 nights in late Spring. Its an amazing place, with great views from the rooms. There were lots of great places to see nearby.

Charming Waterfront Home with Expansive Views
We loved the house; cozy, nicely decorated, with many pieces of original art that really added character. The kitchen is well stocked for those who like to cook. The location right on the water was wonderful, and Nancy provided kayaks, which we took advantage of. Our dog was beside himself with so much room to run. Nancy’s daughter and family live next door, and we spent quite a few hours enjoying conversation and local knowledge with them. We would go back again.
Private cottage rentals

Chesapeake Bay Cottage
The cottage was great. It was exactly we needed. We enjoyed going go Flag Ponds and searching for sharks teeth on the beach

The Blue Crab Beach House - Free beach passes
Very thankful for Danielle’s hospitality and flexibility! We were a last minute booking and had to extend more than once while waiting on movers for our home, and Danielle was ultra helpful in the process. The house was clean, cute, and in a great location for beach visitors. We will absolutely be checking to make sure either the Lazy Crab or Blue Crab are available when we plan to visit the area again! After a cross country trip that consisted of several underwhelming hotels and stays along the way, Danielle’s property was a much needed refresher for my family!

Updated North Beach Cottage: Pet Friendly!
Host was communicative, places was as advertised. It is annoying that this place is a 3 night minimum.

The Lazy Crab Beach House - Free Beach Passes
We had such a wonderful time staying at the Lazy Crab. The house fit our needs perfectly. For a family with a 2 & 4 year old, that isn’t easy to do. The house was clean and we appreciated the extra blankets for the cool nights. The kitchen was also well stocked for cooking at home. If you’re looking for a safe and quiet neighborhood the Lazy Crab is the place for you and your family. Danielle was also a very responsive and friendly host. She even let us leave our bags at the house after check in as our flight was later in the day. Overall, this was a great experience for our first Airbnb as a family and we hope to make this a getaway for us in the future. Thank you Danielle!

The Bayside Cottage STRN 23-3
Most peaceful, relaxing and beautiful place, most responsive host and a comfortable house. We had a great time swimming, exploring the surroundings and watching sunsets from the porch.

Saint Cozy Cottage | waterfront family getaway
Kyli is an excellent host and beautiful home on the water . Great communication and responsive. Awesome place to stay if you are visiting.

Full house rental in Twin Beach. 1 bk from the Bay
This little Chesapeake Cottage is a gem. Located on the border of restaurants on 7th St it's also a stone's throw to the Bay. I could see boats in the Bay while chilling on the wonderful porch. Everything is bright and beachy in the kitchen area. The LR is roomy and cozy. The front porch is a beach house must; it's bright and airy after the heat of the day. I slept soundly in the comfortable bed and luxuriated under the showerhead. I've visited North Beach for over 30 years living locally. I've always dreamed of renting a little cottage close to the Bay and staying a week. Mission accomplished with resounding success. Thank you Heather and Jan!

Cottage on the Creek
Excellent place for a quick weekend trip with my family. Beautiful waterfront view. Lauren and Korey had crab traps already out for us and we were also able to utilize the grill and kayak throughout the weekend. We’d love to stay again in the future!
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- Nationals Park
- The White House
- National Mall
- Georgetown University
- National Museum of African American History and Culture
- Smithsonian National Museum of Natural History
- District Wharf
- Sandy Point State Park
- Arlington National Cemetery
- Washington Monument
- Georgetown Waterfront Park
- National Air and Space Museum
- National Harbor
- Smithsonian American Art Museum
- Meridian Hill Park
- Lincoln Park
- Maryland Renaissance Festival
- American African Museum
- Flounder Pavilion Beach Front - Sandy Point State Park
- Quiet Waters Park
- Ragged Point Beach
- Leesylvania State Park
- International Spy Museum
- Library of Congress