A coastal landscape with a sandy beach, a rocky barrier, and a calm sea.

Rock Hall Vacation Rentals

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Our top choices for Rock Hall vacation rentals

1. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (28 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is CA $168
CA $403 total
includes taxes & fees
Aug 12 - Aug 13
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

2. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (62 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is CA $251
CA $386 total
includes taxes & fees
Aug 24 - Aug 25
BAYSIDE BUNGALOW

3. Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (4 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is CA $244
CA $502 total
includes taxes & fees
Aug 24 - Aug 25
Bayside Cottage steps from Rock Hall Harbor

4. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (119 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is CA $138
CA $221 total
includes taxes & fees
Aug 12 - Aug 13
First Floor Studio Apartment in Historic Chestertown

5. FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
10.0 out of 10, Exceptional, (1 review)
"My wife and I had a great time staying in this houseboat. It was our first time ever trying a houseboat and it did not disappoint us at all. The house was very clean and the host provides fully stocked kitchen cabinets, toiletries, towels, etc...We spent most of our time on the rooftop patio, soaking in the sun, and relaxing by the fire pit playing games. The bed was very comfortable as well. It was a great weekend, at a great house that has the benefit of being in a gated marina which was an...
United States
Justin M.
The price is CA $345
CA $756 total
includes taxes & fees
Aug 25 - Aug 26
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

6. Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (45 reviews)
"Lovely, spacious home in a quiet setting. Ken Island is a beautiful, relaxing spot. Adam was so accommodating and easy to communicate with. The house is well stocked, clean, and comfortable. You’ll enjoy your stay there!"
United States
Susan
The price is CA $148
CA $419 total
includes taxes & fees
Aug 13 - Aug 14
Charming Coastal/Country Home w/3 Acres & Sauna!

7. Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
The price is CA $256
CA $391 total
includes taxes & fees
Aug 19 - Aug 20
Secluded Cottage in Middle of Chestertown

8. Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (40 reviews)
"This was a lovely place for my mom and I to stay - we were dealing with a challenging situation and Solmaz was very kind and was easy to communicate with. The community is nice and parking was easy. "
United States
Linda B.
The price is CA $216
CA $497 total
includes taxes & fees
Sep 1 - Sep 2
Large 2 bedroom house with private parking in a nice neighborhood

9. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (53 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
The price is CA $139
CA $407 total
includes taxes & fees
Aug 12 - Aug 13
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

10. Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (15 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
The price is CA $348
CA $588 total
includes taxes & fees
Aug 12 - Aug 13
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

11. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (6 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is CA $268
CA $678 total
includes taxes & fees
Aug 12 - Aug 13
Pool Loft Suite | Bay Access & Beach Passes

12. Lower Level Loft - Adorable Studio Apt. Near BWI

Lower Level Loft - Adorable Studio Apt. Near BWI
South Gate
9.0 out of 10, Wonderful, (18 reviews)
"That place is incredible—very cozy and clean."
United States
Nataly
The price is CA $91
CA $154 total
includes taxes & fees
Aug 12 - Aug 13
Lower Level Loft - Adorable Studio Apt. Near BWI

13. Idyllic Pasadena Retreat With Garden + Hot Tub!

Idyllic Pasadena Retreat With Garden + Hot Tub!
3.0 star property
Green Haven
The price is CA $312
CA $677 total
includes taxes & fees
Aug 25 - Aug 26
Idyllic Pasadena Retreat With Garden + Hot Tub!

14. Cute, Cozy 2-bedroom house near Annapolis with water access

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.6 out of 10, Exceptional, (19 reviews)
"Highly recommend this property! Great location. Place is clean and host was very accommodating."
United States
Abi O.
The price is CA $119
CA $323 total
includes taxes & fees
Aug 17 - Aug 18
Cute, Cozy 2-bedroom house near Annapolis with water access

15. Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"Perfect location for exploring the cutest town. "
United States
Mandy D.
The price is CA $447
CA $695 total
includes taxes & fees
Sep 2 - Sep 3
Wren Retweet- Country Estate in Center of C’Town

16. Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (26 reviews)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is CA $314
CA $526 total
includes taxes & fees
Aug 31 - Sep 1
Waterfront Retreat with Private Dock and Beach

17. Idyllic Pasadena Retreat with Garden + Hot Tub!

Idyllic Pasadena Retreat with Garden + Hot Tub!
Green Haven
10.0 out of 10, Exceptional, (35 reviews)
"10/10 stars! We had a wonderful stay! It was very clean and well organized! Loved it"
United States
Amy L.
The price is CA $245
CA $691 total
includes taxes & fees
Aug 12 - Aug 13
Idyllic Pasadena Retreat with Garden + Hot Tub!

18. Cozy Fells Point Gem / In The Heart of Fells Point

Cozy Fells Point Gem / In The Heart of Fells Point
Fells Point
9.8 out of 10, Exceptional, (208 reviews)
"Appreciated the privacy."
United States
Marie
The price is CA $72
CA $303 total
includes taxes & fees
Aug 12 - Aug 13
Cozy Fells Point Gem / In The Heart of Fells Point

19. Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio
Fells Point
9.8 out of 10, Exceptional, (98 reviews)
"Awesome place, great location"
United States
Mark M.
The price is CA $72
CA $303 total
includes taxes & fees
Aug 13 - Aug 14
Hidden Fells Point Gem / Private Courtyard Patio

20. Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Arnold
9.8 out of 10, Exceptional, (12 reviews)
"Great place!"
United States
Chris A.
The price is CA $369
CA $749 total
includes taxes & fees
Aug 26 - Aug 27
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront 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 Rock Hall Hotel Reviews

Find out more about Rock Hall

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 Rock Hall. 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

Are there vacation rentals in Rock Hall?

Yes, we give you a choice of vacation rentals in Rock Hall close to The Mainstay, or you can select a more secluded option if you want a relaxing stay. Rock Hall is known for its restaurants and waterfront. Make sure you have time to check out the entertainment choices and parks during your trip.

What are some of the best vacation rentals in Rock Hall?

Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining: This Rock Hall vacation home rental is located near the beach and has a patio, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Another good choice for your trip to Rock Hall is Serene Waterfront Cottage with dock and gorgeous views..

How many vacation rentals are there in Rock Hall?

Choose from 43 Expedia vacation rentals in Rock Hall for a memorable vacation.

What can I see and do in Rock Hall?

Cultural attractions include The Mainstay and Waterman’s Museum, whereas Northern Chesapeake Bay and Chesapeake Bay are a couple of picturesque spots to enjoy the outdoors. Rock Hall Harbor and Ferry Park are other places to visit while you're in town.

What are vacation rentals like in Rock Hall?

Vacation rentals are private accommodations you can stay in for a couple days or more in Rock Hall. Vacation rentals feature amenities such as laundry facilities and kitchens so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from public hotel elevators and busy reception areas while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for family trips.