Search Dares Beach Cottage Rentals from CA $208

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Check prices for these dates

In two weeks
Sep 5 - Sep 7
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16
In four months
Dec 12 - Dec 14

Browse Select Dares Beach Cottages

Family and Pet-Friendly, Waterfront with Pier
Exterior

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (255)
"It is a perfect spot to relax and enjoy the water. We will book again if we are back that way. "
Family and Pet-Friendly, Waterfront with Pier
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Property grounds

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

10.0 out of 10, Exceptional, (7)
"Lovely little rustic cottage full of charm.We arrived over Thanksgiving,the off season was wonderful thank s again"
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Waterfront property with private boat ramp and new dock!
Outdoor dining

Waterfront property with private boat ramp and new dock!

9.4 out of 10, Exceptional, (13)
"Thoroughly enjoyed our stay! Cottage was comfortable and very clean with everything we could have needed! "
Waterfront property with private boat ramp and new dock!
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Marina

"Point of View" Waterfront cottage with panoramic views on Tilghman Island

10.0 out of 10, Exceptional, (11)
"The home was so well appointed and walking distance to stores, restaurants, quaint museums and beautiful nature. The host was so friendly and helpful with quick responses. We had high winds and lots of rain, but stayed cozy and warm. What a friendly Island of people!!"
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
On the beach

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

9.6 out of 10, Exceptional, (4)
"Just the perfect place I needed for a personal retreat. It is quiet, peaceful and serene. I would definitely visit again. "
The price is CA $250
CA $415 total
includes taxes & fees
Aug 27 - Aug 28
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Exterior detail

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

10.0 out of 10, Exceptional, (9)
"Perfect house for a long weekend. Clean, cozy and great communication with Maxine. Would definitely stay here again when I return to Cambridge. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
The Middle Point Cabin in Saint Michaels
Fridge, microwave, oven, stovetop

The Middle Point Cabin in Saint Michaels

9.8 out of 10, Exceptional, (49)
"The property was beautiful, quiet, and peaceful. It was a good refresh from daily life in the city."
The Middle Point Cabin in Saint Michaels
Cozy Cottage with access to and partially obstructed views of the bay.
Beach nearby

Cozy Cottage with access to and partially obstructed views of the bay.

9.2 out of 10, Wonderful, (27)
"Enjoy our time there"
Cozy Cottage with access to and partially obstructed views of the bay.
Quick walk to the beach! Fire pit, Corn hole, Games & More!
Terrace/patio

Quick walk to the beach! Fire pit, Corn hole, Games & More!

10.0 out of 10, Exceptional, (2)
"We loved EVERYTHING about this place. Right next to the beach, great restaurants and shops. Could not have been better service. "
Quick walk to the beach! Fire pit, Corn hole, Games & More!
Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit
Fridge, microwave, oven, stovetop

Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit

10.0 out of 10, Exceptional, (51)
"It’s a wonderful house with everything you need. The views are amazing - perfection! "
Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit
Soul Oasis - home on the Chesapeake Bay
Sun loungers, beach towels

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (31)
"The A-frame cottage was clean and comfortable. I was accompanied by my son and two grandchildren (ages 12 and 14), and we really loved it. We went fishing in bay at the beach area below the cottage, and also did a lot of fossil hunting along the cliffs, which are breathtaking. Our host Teresa was extremely helpful and welcoming. We will definitely be going back!"
The price is CA $208
CA $434 total
includes taxes & fees
Aug 24 - Aug 25
Soul Oasis - home on the Chesapeake Bay
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
Pool

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

9.8 out of 10, Exceptional, (82)
"The cottage was a wonderful place for me and my kids to stay. I really appreciate the thoughtfulness of the owner. We would definitely stay here again."
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
North Beach Cottage - Walk to Chesapeake Bay
Interior

North Beach Cottage - Walk to Chesapeake Bay

10.0 out of 10, Exceptional, (37)
"The house was beautiful with everything you could need. We were out all day so didn’t get to use the house much except for sleeping. The bed was super comfortable."
North Beach Cottage - Walk to Chesapeake Bay
Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb
Dining

Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb

9.6 out of 10, Exceptional, (91)
"We had a great time at this place. Close enough to walk to town if necessary would definitely book again for a weekend getaway."
Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb
Cottage Located on the Patuxent River!
Sun loungers

Cottage Located on the Patuxent River!

10.0 out of 10, Exceptional, (39)
"The accommodations were superb and being on the water was amazing!"
The price is CA $418
CA $500 total
includes taxes & fees
Aug 22 - Aug 23
Cottage Located on the Patuxent River!
Updated North Beach Cottage: Pet Friendly!
Fridge, microwave, stovetop, dishwasher

Updated North Beach Cottage: Pet Friendly!

9.8 out of 10, Exceptional, (19)
"Awesome house a very short walk from Herrington Harbour."
Updated North Beach Cottage: Pet Friendly!
Cottage on the Bay
Sun loungers, beach towels

Cottage on the Bay

8.0 out of 10, Very good, (2)
"We had a wonderful visit! The cottage was exceptionally equipped with towels, kitchen, beach chairs, wood for the fire pit, ect. "
Cottage on the Bay
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
House (3 Bedrooms) | Interior

Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!

3.0 star property
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Interior

Adorable Beach Cottage w/ Hot Tub & Tropical Bar!

3.0 star property
8.0 out of 10, Very good, (2)
"The water is well water and it stinks, water treatment could improve that. This is more in the woods than beachy. In a rundown area. Get some Damprid to cut down on musty smell. Cute decor."
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Waterfront North Beach Home ~ 2 Mi to Beach!
House (2 Bedrooms) | Interior

Waterfront North Beach Home ~ 2 Mi to Beach!

3.0 star property
Waterfront North Beach Home ~ 2 Mi to Beach!
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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Top Dares Beach Hotel Reviews

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

10/10 Excellent
"Everything about this cabin was just what we were looking for! From the initial booking until we left we were taken care of by Brett. The pictures on-line were spot on but seeing the bay view in person from the windows and deck took my breath. There was a lot to do and we took advantage of close by activities (hiking, paddle-boarding, kayaking, jet skiing) but the cabin is a destination in itself with it's peaceful and calm surroundings. We were blessed with beautiful sunrises, hummingbirds and butterfly friends visiting all day and osprey, bald eagle and deer sightings daily! We had an amazing time connecting with nature and each other as a family during our stay!"
Vicki K. 3-night trip
Posted 2 days ago
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay