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

Holiday Rentals in Rock Hall

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Our top choices for Rock Hall holiday 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 €248
includes taxes & fees
30 Aug - 31 Aug
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, (63 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is €275
includes taxes & fees
30 Aug - 31 Aug
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 €309
includes taxes & fees
29 Sept - 30 Sept
Bayside Cottage steps from Rock Hall Harbor

4. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (124 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is €140
includes taxes & fees
8 Sept - 9 Sept
First Floor Studio Apartment in Historic Chestertown

5. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (32 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveller
The price is €307
includes taxes & fees
30 Aug - 31 Aug
Newly restored apartment in the heart of Chestertown

6. 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, (212 reviews)
"We enjoyed our stay. It was a cute little place and perfect for 3 of us. The area is pretty quiet for the most part. We would definitely stay here again."
United States
Tammy
The price is €193
includes taxes & fees
31 Aug - 1 Sept
Cozy Fells Point Gem / In The Heart of Fells Point

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

Lower Level Loft - Adorable Studio Apt. Near BWI
South Gate
9.2 out of 10, Wonderful, (19 reviews)
"That place is incredible—very cozy and clean."
United States
Nataly
The price is €99
includes taxes & fees
1 Sept - 2 Sept
Lower Level Loft - Adorable Studio Apt. Near BWI

8. Lakefront Home Firepit BWI Marleycreek River

Lakefront Home Firepit BWI Marleycreek River
3.0 star property
Marley
The price is €264
includes taxes & fees
3 Sept - 4 Sept
Lakefront Home Firepit BWI Marleycreek River

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (46 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
The price is €247
includes taxes & fees
31 Aug - 1 Sept
Charming Coastal/Country Home w/3 Acres & Sauna!

10. 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 €201
includes taxes & fees
2 Sept - 3 Sept
Hidden Fells Point Gem / Private Courtyard Patio

11. 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 €433
includes taxes & fees
31 Aug - 1 Sept
Wren Retweet- Country Estate in Center of C’Town

12. Cass-Away Luxury Houseboat

Cass-Away Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (107 reviews)
"Wonderful stay. House boat was amazing and hosts helpful and responsive! "
United States
Jamie L.
Cass-Away Luxury Houseboat

13. 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 €247
includes taxes & fees
1 Sept - 2 Sept
Secluded Cottage in Middle of Chestertown

14. Family-friendly home in Baltimore with WiFi, AC, Pool table, Washer & dryer

Family-friendly home in Baltimore with WiFi, AC, Pool table, Washer & dryer
Berea
9.0 out of 10, Wonderful, (11 reviews)
"Listing was better than expected. Highly recommend."
United States
Patrick S.
The price is €175
includes taxes & fees
8 Sept - 9 Sept
Family-friendly home in Baltimore with WiFi, AC, Pool table, Washer & dryer

15. 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, (20 reviews)
"Great stay! Very clean home in a quiet neighborhood. Easy drive to downtown, and there’s a local restaurant right down the street. We really enjoyed our stay!"
United States
Taylor C.
The price is €207
includes taxes & fees
30 Aug - 31 Aug
Cute, Cozy 2-bedroom house near Annapolis with water access

16. 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, (55 reviews)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
The price is €235
includes taxes & fees
30 Aug - 31 Aug
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

17. Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (87 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is €378
includes taxes & fees
1 Sept - 2 Sept
Waterfront Oasis of Annapolis Star

18. 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, (16 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 €359
includes taxes & fees
1 Sept - 2 Sept
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

19. Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Cape Saint Claire
9.6 out of 10, Exceptional, (14 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
The price is €597
includes taxes & fees
30 Aug - 31 Aug
Annapolis Home | Fenced Yard | Pool Table | 10 Guests

20. 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, (2 reviews)
"FLOHOM 14 did not disappoint!!! This was my first stay on a houseboat. Now I know why babies fall asleep when rocked. The boat is beautifully appointed & well equipped. Bring a good book. I’m already missing it!!!"
United States
Maria D.
The price is €496
includes taxes & fees
7 Sept - 8 Sept
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic 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

Everything you need to know about Rock Hall 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 Rock Hall holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 Rock Hall holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Rock Hall holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Rock Hall. 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 Rock Hall 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 Rock Hall holiday rentals we have selected for you start as low as €140 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Rock Hall rentals

At Expedia, we put the best Rock Hall 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 Rock Hall 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 Rock Hall 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 Rock Hall. 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

Are there holiday rentals in Rock Hall?

Yes, there are holiday rentals in Rock Hall close to The Mainstay, or you can select a more secluded option if you're looking for 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 holiday rentals that Rock Hall has to offer?

Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining: This highly rated holiday home rental in Rock Hall is located near the beach, and has a patio, a selection of games and a BBQ 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 holiday rentals are there in Rock Hall?

Choose from 42 Expedia holiday rentals in Rock Hall for a memorable holiday.

What can I see and do in Rock Hall?

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

What are holiday rentals like in Rock Hall?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Rock Hall. Holiday rentals offer extras like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from public hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for family gatherings.