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Dares Beach Vacation Rentals

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Our top choices for Dares Beach vacation rentals

1. Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Prince Frederick
9.2 out of 10, Wonderful, (12 reviews)
"A great place to crash and explore the area."
United States
Sean B.
The price is CA $276
CA $562 total
includes taxes & fees
Nov 20 - Nov 21
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

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

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Very clean and nice property"
United States
Ben W.
The price is CA $201
CA $540 total
includes taxes & fees
Dec 2 - Dec 3
Family Beach House: Spacious Deck, Grill & Views

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, (25 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is CA $132
CA $449 total
includes taxes & fees
Dec 1 - Dec 2
Beachside Oasis with Beach Passes & King Suite by A Haven Away

4. 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 CA $205
CA $442 total
includes taxes & fees
Nov 10 - Nov 11
The Cozy Crab- Your Charming Haven in Lovely North Beach!

5. 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
9.0 out of 10, Wonderful, (16 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 $228
CA $376 total
includes taxes & fees
Nov 10 - Nov 11
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

6. 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 $216
CA $404 total
includes taxes & fees
Nov 16 - Nov 17
3-bedroom house in soothing Saint Leonard with AC for relaxing stays

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, (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 CA $223
CA $639 total
includes taxes & fees
Dec 2 - Dec 3
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

8. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is CA $403
CA $645 total
includes taxes & fees
Nov 10 - Nov 11
Plum Point Cottage #17

9. Plum Point Cottage #15

Plum Point Cottage #15
Maryland
The price is CA $482
CA $803 total
includes taxes & fees
Nov 11 - Nov 12
Plum Point Cottage #15

10. Plum Point Cottage #14

Plum Point Cottage #14
Huntingtown
9.8 out of 10, Exceptional, (10 reviews)
"we had a great stay at this property for an impromptu weekend getaway. "
United States
Yonnick H.
The price is CA $483
CA $763 total
includes taxes & fees
Nov 11 - Nov 12
Plum Point Cottage #14

11. 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 CA $325
CA $517 total
includes taxes & fees
Nov 10 - Nov 11
Bright and airy waterfront getaway

12. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (68 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
The price is CA $211
CA $422 total
includes taxes & fees
Nov 16 - Nov 17
Soul Oasis - home on the Chesapeake Bay

13. 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 CA $192
CA $452 total
includes taxes & fees
Nov 15 - Nov 16
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

14. 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 $223
CA $307 total
includes taxes & fees
Nov 15 - Nov 16
Just a getaway piece of property

15. 2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.

2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.
Cambridge
The price is CA $318
CA $367 total
includes taxes & fees
Nov 11 - Nov 12
2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.

16. 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
10.0 out of 10, Exceptional, (2 reviews)
"Everything at this location was as shown on the listing and it was very clean. We were very satisfied with all elements of this stay. We were there for a weekend and did not use the place heavily, but it suited our needs. It's a quiet location. They had all the major points covered. The only negative comment I have is that the water out of the tap was smelly. I suggest bringing a couple of bottles of water and not drinking the water out of the taps. This is obviously a well maintained home...
United States
Amelia
The price is CA $254
CA $617 total
includes taxes & fees
Nov 13 - Nov 14
3-bedroom house in Deale located on Bay many amenities and great views

17. 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, (17 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is CA $405
CA $709 total
includes taxes & fees
Dec 1 - Dec 2
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

18. 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 $612
CA $1,531 total
includes taxes & fees
Nov 10 - Nov 11
Lakefront Cabin Near Solomons Island w/ Hot Tub

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

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Lusby
9.8 out of 10, Exceptional, (16 reviews)
"Nice house in a great location. Great for groups."
United States
Anonymous traveller
The price is CA $653
CA $1,158 total
includes taxes & fees
Nov 10 - Nov 11
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

20. 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 $242
CA $507 total
includes taxes & fees
Nov 10 - Nov 11
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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.