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Dares Beach Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Dares Beach vacation rentals

A single-story house with a gabled roof, a front porch, and a small front yard with a flag.

1. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is CA $383
CA $650 total
includes taxes & fees
Sep 25 - Sep 26
Plum Point Cottage #17
A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

2. 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 CA $239
CA $405 total
includes taxes & fees
Sep 28 - Sep 29
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

3. Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
The price is CA $221
CA $669 total
includes taxes & fees
Oct 20 - Oct 21
Family Beach House: Spacious Deck, Grill & Views
A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

4. 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 CA $171
CA $366 total
includes taxes & fees
Oct 7 - Oct 8
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
A lakeside view with chairs and a table, a rainbow, and trees.

5. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (24 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 CA $324
CA $543 total
includes taxes & fees
Sep 29 - Sep 30
Bright and airy waterfront getaway
A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

6. 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 CA $124
CA $473 total
includes taxes & fees
Sep 28 - Sep 29
Beachside Oasis with Beach Passes & King Suite by A Haven Away
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 CA $136
CA $542 total
includes taxes & fees
Sep 29 - Sep 30
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, (63 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
The price is CA $211
CA $438 total
includes taxes & fees
Sep 30 - Oct 1
Soul Oasis - home on the Chesapeake Bay
A laundry room with a washing machine and dryer, wooden cabinets above, and a shelf with a bottle.

9. 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 CA $320
CA $617 total
includes taxes & fees
Sep 28 - Sep 29
Rose Haven Coastal Cottage

10. 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 CA $222
CA $319 total
includes taxes & fees
Oct 3 - Oct 4
Just a getaway piece of property
A living room with a sofa, coffee table, fireplace, and artwork on the wall.

11. 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 CA $320
CA $692 total
includes taxes & fees
Sep 30 - Oct 1
3-bedroom house in Deale located on Bay many amenities and great views
A covered outdoor dining area with a table and chairs, overlooking a body of water and trees.

12. Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (45 reviews)
The price is CA $503
CA $631 total
includes taxes & fees
Sep 27 - Sep 28
Sunset Breezes - quiet waterfront retreat
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

13. 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 CA $468
CA $872 total
includes taxes & fees
Oct 7 - Oct 8
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A spacious cabin interior with a wooden ceiling, a kitchen area, a living room with a sofa, and a dining table.

14. 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 CA $654
CA $1,694 total
includes taxes & fees
Oct 5 - Oct 6
Lakefront Cabin Near Solomons Island w/ Hot Tub
A spacious living room with a large sofa, a television, and a view of the ocean.

15. 4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is CA $422
CA $1,020 total
includes taxes & fees
Oct 6 - Oct 7
4-BR Waterfront Turret Home
A pathway lined with trees and lights leading to a wooden building with a visible window.

16. 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 CA $650
CA $1,214 total
includes taxes & fees
Oct 7 - Oct 8
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
A deck with outdoor furniture, a red door, and a house with windows.

17. 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 CA $256
CA $549 total
includes taxes & fees
Sep 30 - Oct 1
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A spacious cabin interior with a wooden ceiling, a kitchen area, a living room with a sofa, and a dining table.

18. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
3.0 star property
Lusby
The price is CA $771
CA $1,667 total
includes taxes & fees
Sep 28 - Sep 29
Lakefront Cabin Near Solomons Island w/ Hot Tub
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

19. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."
United States
Michelle H.
The price is CA $436
CA $818 total
includes taxes & fees
Oct 6 - Oct 7
Sunset Cottage - West River Access and Views!
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 CA $650
CA $1,396 total
includes taxes & fees
Oct 6 - Oct 7
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

Wylder Tilghman Island

Wylder Tilghman Island

10/10 Excellent
"Everything exceeded expectations — particularly the staff — but the breakfast offering, which fell below."
Kendrick 3-night trip
Posted 22 hours ago
Wylder Tilghman Island

Find out more about Dares Beach

Everything you need to know about Dares Beach vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Dares Beach vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Dares Beach vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Dares Beach vacation rentals we have selected for you start as low as CA $366 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 vacation 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 vacation.

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 vacation rentals in Dares Beach?

Yes, you can find vacation rentals near well known points of interest in Dares Beach, or you can choose a more remote option if you're looking for a relaxing stay.

What are some of the best vacation rentals in Dares Beach?

Cottage with Private Water Access | Pet-Friendly | Near St. Michaels: This vacation 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 vacation rentals are there in Dares Beach?

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

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 larger area, you’ll find Breezy Point Beach and Matoaka Beach.

What are vacation rentals like in Dares Beach?

Vacation rentals are private properties you can stay in for a short or long stay in Dares Beach. Vacation rentals offer extras such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for family trips or small group gatherings.