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

Rock Hall Vacation Rentals

Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Rock Hall vacation rentals

Exterior detail

1. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (64 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
$260 nightly
The price is $287
Sep 10 - Sep 11
Total with taxes and fees
BAYSIDE BUNGALOW
Beach

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, (29 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
$257 nightly
The price is $284
Sep 9 - Sep 10
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Smart TV

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.
$383 nightly
The price is $406
Sep 30 - Oct 1
Total with taxes and fees
Bayside Cottage steps from Rock Hall Harbor
Property grounds

4. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (125 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
$144 nightly
The price is $159
Sep 9 - Sep 10
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Smart TV, books

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 traveler
$320 nightly
The price is $353
Sep 9 - Sep 10
Total with taxes and fees
Newly restored apartment in the heart of Chestertown
Property grounds

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.
$463 nightly
The price is $481
Sep 9 - Sep 10
Total with taxes and fees
Wren Retweet- Country Estate in Center of C’Town
Exterior

7. 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.
$296 nightly
The price is $320
Sep 17 - Sep 18
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!
TV, fireplace

8. 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.
$269 nightly
The price is $279
Sep 13 - Sep 14
Total with taxes and fees
Secluded Cottage in Middle of Chestertown
Dining

9. 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
$398 nightly
The price is $422
Sep 9 - Sep 10
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Interior

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, (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.
$293 nightly
The price is $333
Sep 9 - Sep 10
Total with taxes and fees
Large 2 bedroom house with private parking in a nice neighborhood
Property grounds

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.
$381 nightly
The price is $434
Sep 15 - Sep 16
Total with taxes and fees
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Property grounds

12. Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (23 reviews)
"Excellent Property"
United States
Buu T.
$583 nightly
The price is $665
Sep 9 - Sep 10
Total with taxes and fees
Chesapeake Cottages- 2 Quaint Waterfront Retreats
House (3 Bedrooms) | Interior

13. Lakefront Home Firepit BWI Marleycreek River

Lakefront Home Firepit BWI Marleycreek River
3.0 star property
Marley
$270 nightly
The price is $308
Sep 9 - Sep 10
Total with taxes and fees
Lakefront Home Firepit BWI Marleycreek River
Coffee/tea maker, fridge, microwave, oven

14. 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.
$423 nightly
The price is $482
Sep 9 - Sep 10
Total with taxes and fees
Pool Loft Suite | Bay Access & Beach Passes
Smart TV

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

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
$270 nightly
The price is $286
Oct 5 - Oct 6
Total with taxes and fees
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
TV, offices

16. Serenity on the Cove

Serenity on the Cove
Dundalk
9.8 out of 10, Exceptional, (9 reviews)
"Great stay - would stay again "
United States
Anonymous traveler
$945 nightly
The price is $1,091
Sep 13 - Sep 14
Total with taxes and fees
Serenity on the Cove
Exterior

17. 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.
$275 nightly
The price is $297
Sep 16 - Sep 17
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Property grounds

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
9.0 out of 10, Wonderful, (16 reviews)
"Quiet neighborhood, worked well for our group of 8."
United States
Jennifer H.
$505 nightly
The price is $575
Sep 9 - Sep 10
Total with taxes and fees
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
Terrace/patio

19. 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.
$318 nightly
The price is $362
Sep 15 - Sep 16
Total with taxes and fees
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Beach nearby

20. Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (26 reviews)
"Everything was lovely! The dock was beautiful and the accommodations were comfortable.Thanks!"
United States
Max G.
$286 nightly
The price is $316
Oct 4 - Oct 5
Total with taxes and fees
Waterfront Retreat with Private Dock and Beach
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
"The best thing about this hotel is the location. Right behind it is the historic charm. It’s one of the best in the country. The staff was very helpful. The room was spacious. The room was clean. The only thing it needed was newer television monitors. We were trying to watch the U.S. Open tennis and it was hard to follow the ball. Overall, excellent."
Pete 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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Rock Hall vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Rock Hall vacation 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 low season months. For more hustle and bustle, you may prefer to visit Rock Hall in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $186 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Rock Hall rentals

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

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.

Explore a world of travel with Expedia

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 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.