Holiday Rentals in Dares Beach

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Check prices for these dates

In two weeks
31 Oct - 2 Nov
In two months
12 Dec - 14 Dec
In three months
9 Jan - 11 Jan
In four months
6 Feb - 8 Feb

Holiday Rentals in Dares Beach

Outdoor dining
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
9.8 out of 10, Exceptional, (49)
"Our large family of adults and two one-year-olds and a dog had a perfect week. The hosts were kind and responsive, and the home was spacious with lots of room for privacy and being all together. Looking forward to going again!"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Outdoor dining
The Cozy Crab- Your Charming Haven in Lovely North Beach!
The Cozy Crab- Your Charming Haven in Lovely North Beach!
9.8 out of 10, Exceptional, (11)
"Great place. Just a short drive to town with shops, restaurants, and boardwalk."
The Cozy Crab- Your Charming Haven in Lovely North Beach!
Dining
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
10.0 out of 10, Exceptional, (180)
"Cottage was just as pictured. Lots of character and charm. Host, Brett was easy to work with and very helpful!"
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Smart TV, printers
Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More
Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More
10.0 out of 10, Exceptional, (4)
"My first thought was "gorgeous", when i walked through the door. This was just the weekend I needed. The screened in porch was relaxing. Be ready to take pictures of the sunrise! "
Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More
Exterior detail
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
10.0 out of 10, Exceptional, (12)
"Really nice property. Relaxing weekend. Stayed here with my daughter for two nights. We had a great time. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Dining
Million Dollar View of the Chesapeake Bay
Million Dollar View of the Chesapeake Bay
9.8 out of 10, Exceptional, (129)
"We just enjoyed our fourth year at Million Dollar View of the Chesapeake Bay and already look forward to our next vacation at this wonderful home!"
Million Dollar View of the Chesapeake Bay
Interior
Waterfront Wildlife Retreat on the Patuxent River
Waterfront Wildlife Retreat on the Patuxent River
10.0 out of 10, Exceptional, (171)
"We went here just for a little weekend getaway for my boyfriend, his brother, his brother’s girlfriend and their kids. We had the absolute best time, such a nice getaway even if it was only for 3 days. The view of the bay from the house is gorgeous and everything was perfect. I will be recommending this stay to anyone I can! "
Waterfront Wildlife Retreat on the Patuxent River
Exterior
Family and Pet-Friendly, Waterfront with Pier
Family and Pet-Friendly, Waterfront with Pier
10.0 out of 10, Exceptional, (259)
"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
Smart TV, fireplace
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
10.0 out of 10, Exceptional, (58)
"Such a beautiful place to stay. Had absolutely everything you could need. Comfy beds and tons of space. Definitely recommend staying here!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Interior
Waterfront Solomons Apartment
Waterfront Solomons Apartment
9.2 out of 10, Wonderful, (13)
"Very clean, awesome location and amazing hosts!! "
The price is €228
includes taxes & fees
18 Oct - 19 Oct
Waterfront Solomons Apartment
Marina
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
10.0 out of 10, Exceptional, (14)
"We had a wonderful stay at the Point of a View Cottage! The views are spectacular and we also enjoyed how easy it was to walk to places to eat and the local market. Recommendations for places to eat were spot on and also appreciated a message over the weekend notifying us of the local craft market held Sunday morning. Would love to come again one day! "
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Outdoor pool, a heated pool
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
9.8 out of 10, Exceptional, (74)
"We sought a large home for a special family birthday, with multiple bedrooms, roomy eating and living areas, and water access for recreation. This house met all our requirements and more. Our grandchildren, from teen to preschool, loved the multiple kayaks, the crab traps, roasting marshmallows at the fire pit, swimming in the heated pool, finding oyster shells along the shoreline. We visited Annapolis for a sail and sightseeing, even though it meant driving back over the Bay bridge, and we...
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Fridge, microwave, oven, stovetop
Cozy Cottage with access to and partially obstructed views of the bay.
Cozy Cottage with access to and partially obstructed views of the bay.
9.0 out of 10, Wonderful, (30)
"Property was cozy and clean. Owners left lights on for us knowing we had a late arrival. Would definitely stay again. "
Cozy Cottage with access to and partially obstructed views of the bay.
On the beach
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.
9.6 out of 10, Exceptional, (5)
"Just the perfect place I needed for a personal retreat. It is quiet, peaceful and serene. I would definitely visit again. "
The price is €263
includes taxes & fees
17 Oct - 18 Oct
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Dining
Waterfront- 5-bedroom house with dock in charming North Beach
Waterfront- 5-bedroom house with dock in charming North Beach
2.0 star property
10.0 out of 10, Exceptional, (2)
"Lovely home with beautiful views of the Bay. Very spacious and well appointed. The hosts were very responsive to our questions. Great place to celebrate our birthdays with all the family including grandkids. Very convenient to North Beach. "
Waterfront- 5-bedroom house with dock in charming North Beach
Fridge, microwave, oven, stovetop
Sweet Bamboo Beach Cottage
Sweet Bamboo Beach Cottage
9.8 out of 10, Exceptional, (80)
"Cute and clean house..close to beach and restaurants!! We will visit again !"
Sweet Bamboo Beach Cottage
Beach nearby, sun-loungers, beach towels
The Blue Crab Beach House - Free beach passes
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (73)
"The cleanliness, coziness, and convenience was great — exactly as described on the website. We would definitely recommend this VRBO to whoever was looking for a place in North Beach! "
The Blue Crab Beach House - Free beach passes
Private beach
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
10.0 out of 10, Exceptional, (18)
"Gorgeous views and location. "
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
Property grounds
NEW: Life on the River! Luxury estate with jacuzzi and private pier!
NEW: Life on the River! Luxury estate with jacuzzi and private pier!
10.0 out of 10, Exceptional, (31)
"The Blue Pearl exceeded our expectations. Our stay was pure luxury. The host has thought of every possible amenity from the towel warmer to the kayaks to the gourmet kitchen. Having fresh steamed crab caught that day right off of the dock was a wonderful experience. "
NEW: Life on the River! Luxury estate with jacuzzi and private pier!
Beach nearby, sun-loungers, beach towels
Heated pool, sandy beach, pier, and playground set punch point apart!
Heated pool, sandy beach, pier, and playground set punch point apart!
10.0 out of 10, Exceptional, (11)
"We had a wonderful stay! The home has plenty of room, it is clean, quiet and fully stocked. Property management is very responsive and helpful. The activities available at the home and in nearby St. Michael's made our trip especially memorable!"
Heated pool, sandy beach, pier, and playground set punch point apart!
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

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina

10/10 Excellent
"View from the balcony was beautiful. We love the water and love boats. unusual and most welcome was the number of outlets for chargers. We have hearing aids, toothbrushes, phones, Apple watch, etc. The only shortcoming was the continental breakfast. Prepackaged muffins and pastries are poor quality. We were disappointed with those."
Cheryle 3-night trip
Posted 5 days ago
Anchored Inn at Hidden Harbour Marina

Find out more about Dares Beach

Everything you need to know about Dares Beach holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Dares Beach holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Dares Beach holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Dares Beach holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Dares Beach. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Dares Beach holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Dares Beach holiday rentals we have selected for you start as low as €228 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Dares Beach rentals

At Expedia, we put the best Dares Beach holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Dares Beach rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Dares Beach holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Dares Beach. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Dares Beach?

Yes, there are holiday rentals close to the most popular sights in Dares Beach, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Dares Beach has to offer?

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub: This holiday home rental outside of Dares Beach is located on the waterfront, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and 1 hot tub so that you can immerse yourself in your holiday.

What can I see and do in Dares Beach?

While exploring the area, visit family-friendly sights like Chesapeake Beach Railway Museum, or get outside and enjoy nature at Breezy Point Beach. In the wider area, you’ll find Battle Creek Cypress Swamp Sanctuary and Matoaka Beach.

What are holiday rentals like in Dares Beach?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Dares Beach. Holiday rentals feature extras like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and busy front desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for small groups.