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

Rock Hall Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Rock Hall vacation rentals

A house with a blue front door, two windows, and a small porch.

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 CA $189
CA $414 total
includes taxes & fees
Nov 14 - Nov 15
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 CA $282
CA $425 total
includes taxes & fees
Nov 11 - Nov 12
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 CA $140
CA $212 total
includes taxes & fees
Nov 19 - Nov 20
First Floor Studio Apartment in Historic Chestertown
A deck with a view of a marina, including boats and docks.

4. 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 CA $127
CA $366 total
includes taxes & fees
Nov 12 - Nov 13
Cass-N-Reel Luxury Houseboat
A dining area with a wooden table and chairs, a kitchen in the background, and a staircase leading to another level.

5. 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 CA $119
CA $392 total
includes taxes & fees
Nov 11 - Nov 12
Charming Coastal/Country Home w/3 Acres & Sauna!
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, (35 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 CA $318
CA $475 total
includes taxes & fees
Nov 15 - Nov 16
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 CA $297
CA $635 total
includes taxes & fees
Nov 15 - Nov 16
Bay Sunsets for Two • Rooftop Fire Pit
A kitchen with a wooden island, built-in cabinets, and a window providing a view of the outdoors.

8. 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 CA $280
CA $385 total
includes taxes & fees
Nov 30 - Dec 1
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Stylish kitchen with open layout and island seating

9. 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 CA $272
CA $650 total
includes taxes & fees
Nov 11 - Nov 12
Pool Loft Suite | Bay Access & Beach Passes
A bedroom with a bed, a desk, a chair, a ceiling fan, a TV, and a window.

10. 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 CA $191
CA $444 total
includes taxes & fees
Nov 16 - Nov 17
Large 2 bedroom house with private parking in a nice neighborhood
A living room with a sofa, a coffee table, a dining table with chairs, a lamp, and a beach-themed artwork on the wall.

11. 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 CA $100
CA $134 total
includes taxes & fees
Nov 16 - Nov 17
Lower Level Loft - Adorable Studio Apt. Near BWI
A kitchen with wooden cabinets, a stove, and a dining table with chairs.

12. Family Friendly Cozy 3 Bedroom Duplex

Family Friendly Cozy 3 Bedroom Duplex
Grasonville
The price is CA $381
CA $439 total
includes taxes & fees
Nov 24 - Nov 25
Family Friendly Cozy 3 Bedroom Duplex
A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with bar stools.

13. 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 CA $93
CA $278 total
includes taxes & fees
Nov 15 - Nov 16
Cute, Cozy 2-bedroom house near Annapolis with water access
A narrow hallway with wooden flooring, a white door, and a mirror on the wall.

14. Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio
Fells Point
9.8 out of 10, Exceptional, (103 reviews)
"Awesome place, great location"
United States
Mark M.
The price is CA $80
CA $292 total
includes taxes & fees
Nov 22 - Nov 23
Hidden Fells Point Gem / Private Courtyard Patio
Aft deck with spiral staircase to the rooftop, sliding glass doors, and an unobstructed sunset view across the Magothy River from Ferry Point Marina.

15. 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 CA $247
CA $563 total
includes taxes & fees
Nov 15 - Nov 16
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.

16. 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 CA $234
CA $575 total
includes taxes & fees
Nov 16 - Nov 17
The Hideaway Spot- Waterfront w/ Dock on Long Cove
A kitchen with wooden cabinets, a microwave, a coffee maker, and a dishwasher.

17. 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 CA $80
CA $305 total
includes taxes & fees
Nov 18 - Nov 19
Cozy Fells Point Gem / In The Heart of Fells Point
A covered outdoor seating area with wicker furniture, a ceiling fan, and a view of trees and houses.

18. 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
9.2 out of 10, Wonderful, (19 reviews)
"Quiet neighborhood, worked well for our group of 8."
United States
Jennifer H.
The price is CA $521
CA $916 total
includes taxes & fees
Nov 15 - Nov 16
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Rock Hall Hotel Reviews

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"The hot tub was broken. But the staff was helpful, the rooms were big and clean"
Brian 1-night trip
Posted 12 hours ago
Crowne Plaza Annapolis by IHG

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?

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.