Cottage holiday rentals in Calvert County

Find and book unique cottages on Airbnb

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Popular amenities for Calvert County cottage rentals

Cottage rentals with a hot tub

Superhost
Cottage in Annapolis
4.85 out of 5 average rating, 86 reviews

Waterfront cottage w/hot tub/ gated/ pier/ firepit

MichaelRating, 5 stars3 weeks ago
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.
Top Guest favourite
Cottage in Woolford
5 out of 5 average rating, 65 reviews

Waterfront Cottage, Pier, Sunsets, Hot Tub,Kayaks

KathyRating, 5 starstoday
The house is wonderful! We enjoyed being in the fenced backyard with our dogs, hanging out on the dock watching the boats go by, or just sitting in the house admiring the view through the huge picture windows. It was very clean and had all that we needed for a relaxing get away weekend. Natalie was very responsive and very helpful with great local suggestions. Emily's Produce is only a few minutes away and has everything we needed, including fully cooked meals. We can't wait to come back!
Top Guest favourite
Cottage in Easton
5 out of 5 average rating, 106 reviews

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

MeganRating, 5 stars4 days ago
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.
Guest favourite
Cottage in Annapolis
4.86 out of 5 average rating, 107 reviews

Nautical Vibe Walk 2 Harbor Pubs USNA

JohnRating, 5 stars1 month ago
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.
Cottage in Chesapeake Beach
4.52 out of 5 average rating, 21 reviews

Adorable Beach Cottage w/ Hot Tub & Tropical Bar!

EstherRating, 5 stars1 month ago
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
Guest favourite
Cottage in Montross
4.93 out of 5 average rating, 94 reviews

Lakefront/Dock, Cove, Boats, HotTub, Woods & Beach

MilotRating, 5 stars3 weeks ago
Genuinely one of the most pristine and peaceful places I’ve ever been at a great time, weather with family or friends
Guest favourite
Cottage in Lusby
4.89 out of 5 average rating, 44 reviews

Hot Tub Hideaway by Shark Tooth Shores

RebeccaRating, 5 stars4 weeks ago
Surrounded by trees and the sound of waves- perfect place to relax & unwind. Quick but steep hike to the secret beach. Cool spot and more shell than I expected. Kyli was a responsive host, answered all my questions. Also, recommended Island Hideaway for dinner and it was amazing. Homemade pasta and desserts made in house daily. Great views and delicious foods & drinks.

Pet-friendly cottage rentals

Top Guest favourite
Cottage in Saint Michaels
4.98 out of 5 average rating, 237 reviews

The Little Anchor Cottage, St. Michaels, MD

RoxanaRating, 5 stars1 week ago
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.
Superhost
Cottage in Wittman
4.87 out of 5 average rating, 151 reviews

Perfect St. Michaels Getaway

SamRating, 5 stars1 month ago
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.
Top Guest favourite
Cottage in Annapolis
4.96 out of 5 average rating, 408 reviews

Relaxing Water Views - Mill Creek Cottage

EdwardRating, 5 stars1 week ago
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!
Superhost
Cottage in Colonial Beach
4.94 out of 5 average rating, 170 reviews

Bayside Cottage- In the Town with views

KimberlyRating, 5 stars1 month ago
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.
Guest favourite
Cottage in Deale
4.82 out of 5 average rating, 182 reviews

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

LaurieRating, 5 stars1 week ago
The cottage was in a perfect location for my sisters and I to stay for our "sisters weekend" escape. The setting is beautiful and so relaxing. There was plenty of room for us and everything was clean and tidy. We took advantage of the kayaks during the day and had a wonderful fire with s'mores in the evening looking out over the water. We will be back!
Guest favourite
Cottage in Annapolis
4.93 out of 5 average rating, 202 reviews

Secluded Cottage_ A+ Amenities in Historic Dwntwn

RogerRating, 5 stars1 month ago
Perfectly located, walked everywhere. Clean and comfortable.
Guest favourite
Cottage in Cambridge
4.98 out of 5 average rating, 49 reviews

Cozy Cottage on the Bay

SarahRating, 5 stars6 months ago
My husband, dog, and I enjoyed a wonderful Thanksgiving break at this very nice and beautifully situated cottage! The views from the back deck and kitchen are as gorgeous as the listing photos suggest and, while the house is right next door to another one, we heard not a peep from the neighbors during our 5 days there. Everything was very attractive and well thought out - the kitchen was well appointed with everything we needed; the chairs, sofa, and bed were super comfy, the bathroom was clean and cheerful. Maxine was great host, answering all our questions quickly and helpfully. It's a 15-20 minute drive to downtown Cambridge, where we had nice dinners out in town at Blue Ruin and Bombay Social. We also took good day trips to Easton, St. Michaels, the Blackwater National Wildlife Refuge, and the impressive Harriet Tubman Underground Railroad Park and Visitor Center. The whole area is full of beauty and history, and this cottage was a great home base!
Guest favourite
Cottage in Deale
4.9 out of 5 average rating, 166 reviews

Rockhold Creek Cottage

ShamsRating, 5 stars1 month ago
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.

Private cottage rentals

Cottage in Lusby
4.72 out of 5 average rating, 292 reviews

Chesapeake Bay Cottage

DanielaRating, 5 stars3 weeks ago
The cottage was great. It was exactly we needed. We enjoyed going go Flag Ponds and searching for sharks teeth on the beach
Top Guest favourite
Cottage in North Beach
4.95 out of 5 average rating, 64 reviews

The Blue Crab Beach House - Free beach passes

ColinRating, 5 stars5 months ago
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!
Cottage in North Beach
4.76 out of 5 average rating, 34 reviews

Updated North Beach Cottage: Pet Friendly!

MatthewRating, 5 stars2 weeks ago
Host was communicative, places was as advertised. It is annoying that this place is a 3 night minimum.
Top Guest favourite
Cottage in North Beach
5 out of 5 average rating, 41 reviews

The Lazy Crab Beach House - Free Beach Passes

AngelaRating, 5 stars2 months ago
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!
Cottage in 5, Bay Hundred
5 out of 5 average rating, 4 reviews

The Bayside Cottage STRN 23-3

AnnaRating, 5 stars1 week ago
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.
Top Guest favourite
Cottage in Hollywood
5 out of 5 average rating, 39 reviews

The Little Blue Cottage

AnneRating, 5 stars2 days ago
Loved the cottage! Quiet, peaceful, and homelike, just what we were looking for. We particularly enjoyed the fishing and crabbing- would definitely return!
Guest favourite
Cottage in California
4.89 out of 5 average rating, 44 reviews

Saint Cozy Cottage | waterfront family getaway

KristenRating, 5 stars4 weeks ago
Kyli is an excellent host and beautiful home on the water . Great communication and responsive. Awesome place to stay if you are visiting.
Guest favourite
Cottage in North Beach
4.87 out of 5 average rating, 180 reviews

Full house rental in Twin Beach. 1 bk from the Bay

CarolRating, 5 stars1 week ago
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!

Destinations to explore