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Dares Beach Holiday Rentals

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Dares Beach holiday rentals

A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

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, (7 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is AU$362
includes taxes & fees
16 Sept - 17 Sept
3-bedroom house in soothing Saint Leonard with AC for relaxing stays

2. 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 AU$621
includes taxes & fees
10 Sept - 11 Sept
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

3. 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, (23 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is AU$461
includes taxes & fees
13 Sept - 14 Sept
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

4. 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 AU$369
includes taxes & fees
10 Sept - 11 Sept
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
A single-story house with a gabled roof, a front porch, and a small front yard with a flag.

5. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is AU$625
includes taxes & fees
10 Sept - 11 Sept
Plum Point Cottage #17
A lakeside view with chairs and a table, a rainbow, and trees.

6. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (23 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 AU$489
includes taxes & fees
10 Sept - 11 Sept
Bright and airy waterfront getaway
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

7. 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, (37 reviews)
"We enjoyed our stay in North Beach at this lovely residence. It was spacious, clean, nicely furnished and only a few minutes walk to the bay. The beds were so comfortable too!!"
United States
Penny N.
The price is AU$573
includes taxes & fees
15 Sept - 16 Sept
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A triangular cabin with a wooden staircase leading to a door, surrounded by trees.

8. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (61 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
The price is AU$423
includes taxes & fees
7 Oct - 8 Oct
Soul Oasis - home on the Chesapeake Bay
A house with a yellow door and a window with a lamp outside.

9. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very good, (13 reviews)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
United States
Maude H.
The price is AU$453
includes taxes & fees
10 Sept - 11 Sept
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
A deck with outdoor furniture, a red door, and a house with windows.

10. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Shady Side
9.0 out of 10, Wonderful, (2 reviews)
"The location was spectacular, the host was communicative, and we had a great time! A beautiful and clean home with everything needed to make a trip a success. One small issue with some needed essentials meant a quick run to the store (TP!) but otherwise a great location, great stay, and would stay again!"
United States
David S.
The price is AU$360
includes taxes & fees
10 Sept - 11 Sept
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A laundry room with a washing machine and dryer, wooden cabinets above, and a shelf with a bottle.

11. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
"Great place to stay! Location was nice and close to water views. House was charming and CLEAN. Owners went above and beyond to make the stay welcoming and convenient. Price was reasonable until additional Vrbo fees were added."
United States
Sharon t.
The price is AU$631
includes taxes & fees
15 Sept - 16 Sept
Rose Haven Coastal Cottage

12. 3-bedroom house in serene Lusby with refreshing AC, heat, outdoor fireplace

3-bedroom house in serene Lusby with refreshing AC, heat, outdoor fireplace
Lusby
The price is AU$571
includes taxes & fees
16 Sept - 17 Sept
3-bedroom house in serene Lusby with refreshing AC, heat, outdoor fireplace
A spacious cabin with a wooden interior, a fireplace, a television, and a dining area.

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 AU$1,559
includes taxes & fees
10 Sept - 11 Sept
Lakefront Cabin Near Solomons Island w/ Hot Tub
A covered outdoor dining area with a table and chairs, overlooking a body of water and trees.

14. Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (45 reviews)
"Comfortable, roomy, awesome views!"
United States
John C.
The price is AU$638
includes taxes & fees
4 Oct - 5 Oct
Sunset Breezes - quiet waterfront retreat
A living room with a sofa, coffee table, fireplace, and artwork on the wall.

15. 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 AU$710
includes taxes & fees
30 Sept - 1 Oct
3-bedroom house in Deale located on Bay many amenities and great views
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

16. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Lovely place and neighborhood! "
United States
Marci M.
The price is AU$797
includes taxes & fees
6 Oct - 7 Oct
Sunset Cottage - West River Access and Views!
A spacious living room with a large sofa, a television, and a view of the ocean.

17. 4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is AU$982
includes taxes & fees
21 Sept - 22 Sept
4-BR Waterfront Turret Home
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

18. 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 AU$949
includes taxes & fees
7 Oct - 8 Oct
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A pathway lined with trees and lights leading to a wooden building with a visible window.

19. 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 AU$1,155
includes taxes & fees
28 Sept - 29 Sept
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
A cozy living room with a large sectional sofa, a round woven coffee table, and a ceiling fan.

20. 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, (2 reviews)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is AU$1,324
includes taxes & fees
29 Sept - 30 Sept
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
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

Springhill Suites by Marriott Prince Frederick

Springhill Suites by Marriott Prince Frederick

8/10 Good
"."
Phyllis 1-night trip
Posted 3 hours ago
Springhill Suites by Marriott Prince Frederick

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, 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 favourite 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 depend 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 AU$362 per night. Entering your travel dates in the search wizard might find you 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?

3-bedroom house in soothing Saint Leonard with AC for relaxing stays: This holiday home rental outside of Dares Beach offers a fireplace, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family.

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.