Search Dares Beach Cottage Rentals from CA $206

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Dares Beach Cottages

Waterfront property with private boat ramp and new dock!
Sit and enjoy the view from this shaded patio with a round table and two chairs.

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
Boats docked at the marina, surrounded by trees and buildings.

"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
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Stylish entrance with a wooden staircase and a mailbox.

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

10.0 out of 10, Exceptional, (7)
"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)
Cozy Cottage with access to and partially obstructed views of the bay.
Relax in Adirondack chairs on the beach, overlooking the calm sea.

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

9.0 out of 10, Wonderful, (26)
"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!
Relax in a serene outdoor space surrounded by lush greenery and trees, featuring a fire pit and comfortable seating.

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

10.0 out of 10, Exceptional, (1)
"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
Enjoy cooking in this well-equipped kitchen with a stainless steel stove, oven, and microwave, along with a large sink and gold faucet.

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

10.0 out of 10, Exceptional, (49)
"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
Family and Pet-Friendly, Waterfront with Pier
Escape to a serene forest retreat with a cozy cabin-style lodge featuring a sheltered front porch and breathtaking natural views.

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (253)
"Our stay was great and Rob and Clarissa were very welcoming!"
Family and Pet-Friendly, Waterfront with Pier
Soul Oasis - home on the Chesapeake Bay
Escape to a serene beach paradise surrounded by lush greenery and the soothing sound of gentle waves.

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 $206
CA $432 total
includes taxes & fees
Aug 18 - Aug 19
Soul Oasis - home on the Chesapeake Bay
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Relax under a thatched umbrella in a serene outdoor setting surrounded by lush greenery.

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!
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
Relax by the pool surrounded by lounge chairs and outdoor seating.

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
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
Experience the serene tranquility of a beachside haven, where waves gently lap at the shore and a weathered tree stands sentinel.

Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC

10.0 out of 10, Exceptional, (16)
"The house was very nice and had great amenities supplied by the owners. "
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
North Beach Cottage - Walk to Chesapeake Bay
Enjoy a game of pool in this room with a pool table and expansive views of the backyard through large windows.

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
Cottage Located on the Patuxent River!
Walk along the beach to the wooden pier, where the calm waters await.

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 $414
CA $496 total
includes taxes & fees
Aug 15 - Aug 16
Cottage Located on the Patuxent River!
The Middle Point Cabin in Saint Michaels
Enjoy cooking in this well-equipped kitchen with a dining table for four, appliances, and ample storage.

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
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Enjoy a serene lakeside escape with a picnic table and access to a pebbly 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 $247
CA $414 total
includes taxes & fees
Aug 17 - Aug 18
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Updated North Beach Cottage: Pet Friendly!
Enjoy cooking in this well-equipped kitchen with stainless steel appliances, a large island, and a sink.

Updated North Beach Cottage: Pet Friendly!

9.8 out of 10, Exceptional, (17)
"Awesome house a very short walk from Herrington Harbour."
Updated North Beach Cottage: Pet Friendly!
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
Relax in a spacious living area with a sofa, coffee table, and wicker basket, featuring a kitchen with stainless steel appliances and a granite countertop.

Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!

3.0 star property
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
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!
Coastal Pet-Friendly Cottage < 1/2 Mi to Beaches
Situated in a serene garden, this charming shed offers a simple, functional space.

Coastal Pet-Friendly Cottage < 1/2 Mi to Beaches

8.8 out of 10, Excellent, (5)
"My wife and I stayed at this property for a few days and loved it! The owner was very responsive and was very accommodating. I could really feel the pride in ownership of this cottage that the owner has. There was a very informative welcome booklet with easy to follow instructions for the home and with information about the area. The cottage is centrally located between North Beach and Chesapeake Beach, so it was the best of both words. We can't wait to go back!"
Coastal Pet-Friendly Cottage < 1/2 Mi to Beaches
Tilghman Island Retreat By Knapps Narrows!
House (2 Bedrooms) | Interior

Tilghman Island Retreat By Knapps Narrows!

3.0 star property
Tilghman Island Retreat By Knapps Narrows!
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

The Tilghman Island Inn

The Tilghman Island Inn

10/10 Excellent
"We had the best weekend! The staff were so kind and welcoming. The hotel was clean, quiet and so relaxing. The food was delicious and the drinks were amazing. We will definitely be staying again!!!!"
Erika 2-night trip
Posted 23 hours ago
The Tilghman Island Inn