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

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Rock Hall holiday rentals

A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

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, (33 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is £211
includes taxes & fees
12 Nov - 13 Nov
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A building with a gabled roof and a circular vent on the roof.

2. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (67 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is £227
includes taxes & fees
9 Nov - 10 Nov
BAYSIDE BUNGALOW
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

3. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (133 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is £114
includes taxes & fees
9 Nov - 10 Nov
First Floor Studio Apartment in Historic Chestertown
A garden with a wooden bridge, lush greenery, and a variety of plants.

4. 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 £207
includes taxes & fees
9 Nov - 10 Nov
Secluded Cottage in Middle of Chestertown
A deck with a view of a marina, including boats and docks.

5. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (54 reviews)
"Love This rental. One of our favorites. Small but everything needed. And the view is absolutely wonderful."
United States
Yamilet
The price is £195
includes taxes & fees
12 Nov - 13 Nov
Cass-N-Reel Luxury Houseboat
A spacious living area with a dining table, sofa, and a kitchen in the background.

6. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (34 reviews)
"Enjoyable stay. All was as advertised. The host was very helpful when asked for information. Location was wonderful, very central in the old part of town. We had a great time!"
United States
Susan A.
The price is £253
includes taxes & fees
9 Nov - 10 Nov
Newly restored apartment in the heart of Chestertown
A sunset view from a balcony with a glass-top table and a fire feature, overlooking the sea.

7. Bay Sunsets for Two • Rooftop Fire Pit

Bay Sunsets for Two • Rooftop Fire Pit
Pasadena
10.0 out of 10, Exceptional, (4 reviews)
"We had a phenomenal time celebrating our engagement at Flohom! The space was spotlessly clean, super comfortable, and peaceful. The location was fantastic, and the hosting was top-notch from start to finish. We couldn't have asked for a better experience to"
United States
Charles W.
The price is £350
includes taxes & fees
15 Nov - 16 Nov
Bay Sunsets for Two • Rooftop Fire Pit
A lighthouse with a white exterior, a balcony, and a metal roof.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (50 reviews)
"Great stay"
United States
Michael V.
The price is £202
includes taxes & fees
9 Nov - 10 Nov
Charming Coastal/Country Home w/3 Acres & Sauna!
A covered porch with a wooden bench, potted plants, and a decorative railing.

9. 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 £338
includes taxes & fees
9 Nov - 10 Nov
Wren Retweet- Country Estate in Center of C’Town
A kitchen with a wooden island, built-in cabinets, and a window providing a view of the outdoors.

10. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
8.0 out of 10, Very good, (1 review)
"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...
United States
Miriam G.
The price is £208
includes taxes & fees
14 Nov - 15 Nov
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A kitchen with wooden cabinets, a stainless steel refrigerator, a coffee maker, and a water dispenser.

11. 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, (44 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 £238
includes taxes & fees
9 Nov - 10 Nov
Large 2 bedroom house with private parking in a nice neighborhood
A backyard with a swimming pool, lounge chairs, and umbrellas.

12. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (9 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 £349
includes taxes & fees
9 Nov - 10 Nov
Pool Loft Suite | Bay Access & Beach Passes
Aft deck with spiral staircase to the rooftop, sliding glass doors, and an unobstructed sunset view across the Magothy River from Ferry Point Marina.

13. Houseboat Suite for Two near Annapolis

Houseboat Suite for Two near Annapolis
Arnold
9.8 out of 10, Exceptional, (14 reviews)
"Beautiful location! Amazing restaurant down the street. Best crab dip and cream of crab soup you’ll ever have."
United States
Anonymous traveller
The price is £299
includes taxes & fees
15 Nov - 16 Nov
Houseboat Suite for Two near Annapolis
A cozy cabin interior with a leather sofa, a wooden dining table, and a view of a lake through large windows.

14. The Hideaway Spot- Waterfront w/ Dock on Long Cove

The Hideaway Spot- Waterfront w/ Dock on Long Cove
Glen Burnie
9.4 out of 10, Exceptional, (18 reviews)
"Very clean and well stocked Beautiful location Will definitely book againBroken oar and paddle restaurant nearby excellent food and service"
United States
Chris H.
The price is £263
includes taxes & fees
9 Nov - 10 Nov
The Hideaway Spot- Waterfront w/ Dock on Long Cove
A kitchen with wooden cabinets, a stove, and a dining table with chairs.

15. Family Friendly Cozy 3 Bedroom Duplex

Family Friendly Cozy 3 Bedroom Duplex
Grasonville
The price is £230
includes taxes & fees
10 Nov - 11 Nov
Family Friendly Cozy 3 Bedroom Duplex
A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with bar stools.

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

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.8 out of 10, Exceptional, (31 reviews)
"Great stay"
United States
Guillaume P.
The price is £149
includes taxes & fees
15 Nov - 16 Nov
Cute, Cozy 2-bedroom house near Annapolis with water access
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

17. Relax on Kent Island in 4 Bedroom Home w/Waterview

Relax on Kent Island in 4 Bedroom Home w/Waterview
Stevensville
9.8 out of 10, Exceptional, (57 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
The price is £250
includes taxes & fees
23 Nov - 24 Nov
Relax on Kent Island in 4 Bedroom Home w/Waterview
A waterfront with docked boats, a water taxi, and historic buildings.

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, (217 reviews)
"It’s a cozy, clean, and cute apartment. We enjoyed our stay very much and the location is wonderful…within walking distance of all the restaurants and attractions you could want."
United States
Carol
The price is £166
includes taxes & fees
11 Nov - 12 Nov
Cozy Fells Point Gem / In The Heart of Fells Point
A living room with a sofa, a coffee table, a dining table with chairs, a lamp, and a beach-themed artwork on the wall.

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

Lower Level Loft - Adorable Studio Apt. Near BWI
South Gate
9.0 out of 10, Wonderful, (20 reviews)
"This was an adorable little place, perfect for my husband and I. With a few minor tweaks and upgrades, this would easily be a five star stay. I would happily stay here again. Thank you!"
United States
Deanna
The price is £73
includes taxes & fees
9 Nov - 10 Nov
Lower Level Loft - Adorable Studio Apt. Near BWI
A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

20. Turtle Cove Room

Turtle Cove Room
Kent County
10.0 out of 10, Exceptional, (1 review)
"The host was very communicative. The room was clean. It was quiet and peaceful. There were blackout curtains on the windows. A very pleasant stay."
United States
Jennifer M.
The price is £145
includes taxes & fees
9 Nov - 10 Nov
Turtle Cove Room
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Beautiful inns. Well maintained. Walking distance to the heart of Annapolis."
Eleni 3-night trip
Posted 3 hours ago
Historic Inns of Annapolis

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 £111 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?

Serene Waterfront Cottage with dock and gorgeous views.: This highly rated holiday home rental in Rock Hall is located on the waterfront, and offers a garden, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a microwave.

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.