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Chesapeake Beach
Our top choices for Calvert County cottages
1. Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly
Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-FriendlyAnnapolis
9.8 out of 10, Exceptional, (45 reviews)
"Second year staying here and absolutely love this place! The private beach is fantastic for all our grandchildren to play and swim."
Gregg L.
2. Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.Benedict
9.0 out of 10, Wonderful, (16 reviews)
"Beautiful view from the house. Extremely clean. Had everything we needed. Can't wait to come back"
ed r.
The price is CA $238
CA $386 total
includes taxes & fees
Nov 12 - Nov 13
3. Lovely 2-bedroom waterfront cottage in charming Wittman
Lovely 2-bedroom waterfront cottage in charming WittmanWittman
9.8 out of 10, Exceptional, (8 reviews)
"This lovely cottage was just perfect for us! The house is newly updated & located on a beautiful property right on the water. We loved the firepit, seeing all the stars at night & watching the wildlife on the water. The kayaks were a nice surprise too! We visit MD often & will definitely stay here again!"
Beth H.
4. Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishingNewburg
9.8 out of 10, Exceptional, (174 reviews)
"Excellent vacation. We'll be back in the future."
John C.
5. John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!Downtown St. Michaels
9.6 out of 10, Exceptional, (136 reviews)
"A beautiful, historic home perfectly situated in the heart of St. Michael’s."
Laura C.
6. Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Location, Location, Location! - W Melson House - Beautiful - In Town St MichaelsDowntown St. Michaels
9.6 out of 10, Exceptional, (143 reviews)
"Great location in St Michaels at a fun historical house."
Adam
7. Soul Oasis - home on the Chesapeake Bay
Soul Oasis - home on the Chesapeake BayLusby
10.0 out of 10, Exceptional, (67 reviews)
"Nice, clean, and would absolutely stay here again."
Dusty S.
The price is CA $189
CA $395 total
includes taxes & fees
Dec 1 - Dec 2
8. Relaxing Waterfront Cottage Near St Michaels, Maryland
Relaxing Waterfront Cottage Near St Michaels, MarylandWittman
9.8 out of 10, Exceptional, (264 reviews)
"We had a great time at a great place."
Jeffrey F.
9. Potomac Riverfront! Home Near St Clements Island
Potomac Riverfront! Home Near St Clements IslandColtons Point
8.8 out of 10, Excellent, (3 reviews)
"Nice little place with a great view of the tidal Potomac. Great sunsets. Comfortable beds. Great backyard for a cookout. The dogs loved the yard. We would definitely rent again."
William M.
10. Charming Waterfront Cottage Retreat near St. Michaels
Charming Waterfront Cottage Retreat near St. MichaelsBozman
10.0 out of 10, Exceptional, (13 reviews)
"This was a great stay for my wife and I on our mini moon. Everything was perfect. The property was well equipped with everything we needed, a great location that was private but not too far from town. We will be back!"
Nick G.
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.
Top reviews in Calvert County
The Wildset
The WildsetDowntown St. Michaels
10/10 Excellent
Our stay at the Wildset was amazing! The room was beautiful and clean. The staff were available at all hours and did the most to ensure our stay was special. The hotel has lots of small touches that truly make the experience like bikes, a cafe with coffee and drinks, and smore's kits in the evenings.
Mairi
