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Dares Beach Holiday Rentals

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Our top choices for Dares Beach holiday rentals

1. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Saint Leonard
10.0 out of 10, Exceptional, (8 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is NZ$472
includes taxes & fees
26 Oct - 27 Oct
3-bedroom house in soothing Saint Leonard with AC for relaxing stays

2. Plum Point Cottage #14

Plum Point Cottage #14
Huntingtown
9.8 out of 10, Exceptional, (9 reviews)
"we had a great stay at this property for an impromptu weekend getaway. "
United States
Yonnick H.
The price is NZ$957
includes taxes & fees
18 Oct - 19 Oct
Plum Point Cottage #14

3. Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is NZ$811
includes taxes & fees
9 Nov - 10 Nov
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

4. Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (24 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is NZ$588
includes taxes & fees
21 Oct - 22 Oct
Beachside Oasis with Beach Passes & King Suite by A Haven Away

5. The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!
North Beach
9.6 out of 10, Exceptional, (30 reviews)
"Wonderful place to visit "
United States
James L.
The price is NZ$519
includes taxes & fees
19 Oct - 20 Oct
The Cozy Crab- Your Charming Haven in Lovely North Beach!

6. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (26 reviews)
"Amazing host and home, great view with the water right there, and short drive to any shopping needs. It was the serene getaway I needed to recharge from city life and corporate burnout."
United States
George
The price is NZ$628
includes taxes & fees
18 Oct - 19 Oct
Bright and airy waterfront getaway

7. 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
9.2 out of 10, Wonderful, (15 reviews)
"Beautiful view from the house. Extremely clean. Had everything we needed. Can't wait to come back"
United States
ed r.
The price is NZ$470
includes taxes & fees
18 Oct - 19 Oct
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

8. Plum Point Cottage #15

Plum Point Cottage #15
Maryland
The price is NZ$999
includes taxes & fees
27 Oct - 28 Oct
Plum Point Cottage #15

9. Plum Point Cottage #1

Plum Point Cottage #1
Calvert County
The price is NZ$888
includes taxes & fees
24 Oct - 25 Oct
Plum Point Cottage #1

10. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
10.0 out of 10, Exceptional, (3 reviews)
"Warm and cozy- amazing home, beautiful area"
United States
Sodbileg
The price is NZ$751
includes taxes & fees
18 Oct - 19 Oct
Rose Haven Coastal Cottage

11. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (40 reviews)
"This property and host were excellent. Property was as advertised. Lovely, clean, quiet and comfortable. Owner was super responsive and check in and check out was easy. 100% recommend."
United States
Sarah
The price is NZ$831
includes taxes & fees
9 Nov - 10 Nov
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

12. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is NZ$768
includes taxes & fees
18 Oct - 19 Oct
Plum Point Cottage #17

13. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
Lusby
10.0 out of 10, Exceptional, (2 reviews)
"Very much enjoyed our stay. The host was very kind and responsive and the property very comfortable. Hot tub and quiet location were great!"
United States
Tanya S.
The price is NZ$2,031
includes taxes & fees
18 Oct - 19 Oct
Lakefront Cabin Near Solomons Island w/ Hot Tub

14. WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (16 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is NZ$951
includes taxes & fees
19 Oct - 20 Oct
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

15. Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Lusby
9.6 out of 10, Exceptional, (14 reviews)
"Nice house in a great location. Great for groups."
United States
Anonymous traveller
The price is NZ$1,494
includes taxes & fees
18 Oct - 19 Oct
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

16. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
3.0 star property
Lusby
The price is NZ$2,097
includes taxes & fees
26 Oct - 27 Oct
Lakefront Cabin Near Solomons Island w/ Hot Tub

17. 4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is NZ$1,269
includes taxes & fees
18 Oct - 19 Oct
4-BR Waterfront Turret Home

18. Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Lusby
10.0 out of 10, Exceptional, (3 reviews)
"We loved the quiet location, the privacy, and the dock out back. The house was stocked with everything we needed!"
United States
Nicholas L.
The price is NZ$1,510
includes taxes & fees
20 Oct - 21 Oct
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

19. Just a getaway piece of property

Just a getaway piece of property
Mechanicsville
10.0 out of 10, Exceptional, (1 review)
"Perfect place. Just what i was looking. Definitely recommend to anyone looking to stay close to the MIR track for any event"
United States
David L.
The price is NZ$402
includes taxes & fees
21 Oct - 22 Oct
Just a getaway piece of property

20. 3-bedroom house in Deale located on Bay many amenities and great views

3-bedroom house in Deale located on Bay many amenities and great views
Deale
The price is NZ$763
includes taxes & fees
18 Oct - 19 Oct
3-bedroom house in Deale located on Bay many amenities and great views
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

Find out more about Dares Beach

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Dares Beach holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Dares Beach. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Dares Beach. Seeing all the best attractions is bound to make you fall in love with Dares Beach. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Dares Beach short-term rentals, that won’t be hard to do.

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?

Cottage with Private Water Access | Pet-Friendly | Near St. Michaels: This holiday home rental outside of Dares Beach offers a balcony, a selection of games and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Dares Beach?

Choose from 3 Expedia holiday rentals in Dares Beach for a memorable holiday.

What can I see and do in Dares Beach?

Northern Chesapeake Bay and Chesapeake Bay are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Breezy Point Beach 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.