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

Rock Hall Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Rock Hall vacation rentals

A building with a gabled roof and a circular vent on the roof.

1. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (66 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is AED 735
AED 1,159 total
includes taxes & fees
1 Oct - 2 Oct
BAYSIDE BUNGALOW
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

2. 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, (30 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is AED 455
AED 1,079 total
includes taxes & fees
4 Oct - 5 Oct
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A spacious living room with a leather sofa, a wooden coffee table, and a fireplace.

3. Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (5 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is AED 643
AED 1,335 total
includes taxes & fees
1 Oct - 2 Oct
Bayside Cottage steps from Rock Hall Harbor
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

4. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (128 reviews)
"This property is delightful. It's very "beachy" and relaxing. There are lots of thoughtful amenities which made our stay smooth. The only thing I would mention is that the property is reached by a set of six stair steps, even though strictly speaking it is on the first floor of the house. That wasn't a problem for us. Other than that, we can highly recommend it. We thoroughly enjoyed our stay here. (My husband wants me to mention that he loved the bed and slept very well.)"
United States
Charr
The price is AED 364
AED 583 total
includes taxes & fees
5 Oct - 6 Oct
First Floor Studio Apartment in Historic Chestertown
A living room with a fireplace, patterned furniture, a coffee table, and a bookshelf.

5. 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 AED 674
AED 1,006 total
includes taxes & fees
4 Oct - 5 Oct
Secluded Cottage in Middle of Chestertown
A hallway with wooden flooring, a door on the right, and a window at the end.

6. 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 AED 1,119
AED 1,768 total
includes taxes & fees
6 Oct - 7 Oct
Wren Retweet- Country Estate in Center of C’Town
A modern exterior with a black door, a metal staircase, and a lantern.

7. Cass-Away Luxury Houseboat

Cass-Away Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (108 reviews)
"Wonderful stay. House boat was amazing and hosts helpful and responsive! "
United States
Jamie L.
Cass-Away Luxury Houseboat
A dining area with a wooden table and chairs, beige curtains, and a ceiling light fixture.

8. 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 AED 1,102
AED 1,865 total
includes taxes & fees
1 Oct - 2 Oct
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
A lighthouse with a white exterior, a balcony, and a metal roof.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (47 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 AED 391
AED 1,084 total
includes taxes & fees
4 Oct - 5 Oct
Charming Coastal/Country Home w/3 Acres & Sauna!
A modern kitchen with stainless steel appliances, white cabinetry, and a brick backsplash.

10. B’more Restful. Comfortable Townhome -Easy access to everywhere

B’more Restful. Comfortable Townhome -Easy access to everywhere
Dundalk
10.0 out of 10, Exceptional, (15 reviews)
"very wonderful home and very quite area "
United States
alan d.
The price is AED 731
AED 1,264 total
includes taxes & fees
1 Oct - 2 Oct
B’more Restful. Comfortable Townhome -Easy access to everywhere
A sunset view from a balcony with a glass-top table and a fire feature, overlooking the sea.

11. 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 AED 694
AED 1,696 total
includes taxes & fees
8 Oct - 9 Oct
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
A wooden dock with Adirondack chairs and a ladder, overlooking a calm body of water with a distant shoreline.

12. Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (24 reviews)
"Excellent Property"
United States
Buu T.
The price is AED 1,322
AED 2,441 total
includes taxes & fees
5 Oct - 6 Oct
Chesapeake Cottages- 2 Quaint Waterfront Retreats
A modern kitchen with dark cabinets, a white countertop, and a large window.

13. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (51 reviews)
"Had a great time, great property and great location."
United States
Danny B.
Cass-N-Reel Luxury Houseboat
A house with a deck, a fire pit, and blue Adirondack chairs.

14. Lakefront Home Firepit BWI Marleycreek River

Lakefront Home Firepit BWI Marleycreek River
3.0 star property
Marley
The price is AED 1,003
AED 1,194 total
includes taxes & fees
18 Oct - 19 Oct
Lakefront Home Firepit BWI Marleycreek River
A kitchen with wooden cabinets, a stainless steel refrigerator, a coffee maker, and a water dispenser.

15. 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, (41 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 AED 512
AED 1,229 total
includes taxes & fees
1 Oct - 2 Oct
Large 2 bedroom house with private parking in a nice neighborhood
A kitchen with wooden cabinets, a dining table, and a refrigerator.

16. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (13 reviews)
"We had an amazing stay for a wedding weekend! Beautiful grounds, beautiful house, lots of room for kids and dogs. Would definitely stay again! "
United States
Emily C.
Family Retreat at Lansdowne Manor
A deck with outdoor furniture, a potted plant, and a house in the background.

17. 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 AED 808
AED 1,133 total
includes taxes & fees
7 Oct - 8 Oct
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Stylish kitchen with open layout and island seating

18. 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 AED 1,014
AED 2,169 total
includes taxes & fees
18 Oct - 19 Oct
Pool Loft Suite | Bay Access & Beach Passes
A sandy beach with a wooden walkway leading to a calm lake, surrounded by dense green foliage.

19. Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
9.8 out of 10, Exceptional, (27 reviews)
"Everything was lovely! The dock was beautiful and the accommodations were comfortable.Thanks!"
United States
Max G.
The price is AED 643
AED 1,159 total
includes taxes & fees
12 Oct - 13 Oct
Waterfront Retreat with Private Dock and Beach
A covered outdoor seating area with wicker furniture, a ceiling fan, and a view of trees and houses.

20. Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
Cape Saint Claire
9.0 out of 10, Wonderful, (17 reviews)
"Quiet neighborhood, worked well for our group of 8."
United States
Jennifer H.
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
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

8/10 Good
"Parking You will have to use a garage or pay hotel $50.00 per night"
HAL 2-night trip
Posted 3 hours ago
Historic Inns of Annapolis

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?

Serene Waterfront Cottage with dock and gorgeous views.: Visitors give good reviews to this Rock Hall vacation home rental, which 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 vacation rentals are there in Rock Hall?

Choose from 42 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 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 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.