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
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Rock Hall vacation 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, (30 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
$257 nightly
The price is $284
Oct 25 - Oct 26
Total with taxes and fees
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.
$286 nightly
The price is $316
Oct 26 - Oct 27
Total with taxes and fees
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, (130 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
$144 nightly
The price is $159
Oct 26 - Oct 27
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
A living room with a fireplace, patterned furniture, a coffee table, and a bookshelf.

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.
$264 nightly
The price is $274
Oct 25 - Oct 26
Total with taxes and fees
Secluded Cottage in Middle of Chestertown
A lighthouse with a white exterior, a balcony, and a metal roof.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (48 reviews)
"Great stay"
United States
Michael V.
$243 nightly
The price is $260
Oct 25 - Oct 26
Total with taxes and fees
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, (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.
$320 nightly
The price is $353
Oct 26 - Oct 27
Total with taxes and fees
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. 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, (3 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.
$373 nightly
The price is $425
Nov 2 - Nov 3
Total with taxes and fees
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
A living room with a brown leather sofa, a wooden coffee table, and a ceiling fan.

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.
$269 nightly
The price is $285
Nov 1 - Nov 2
Total with taxes and fees
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A wooden door, a rug, a cabinet, and a lamp.

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.
$464 nightly
The price is $482
Nov 3 - Nov 4
Total with taxes and fees
Wren Retweet- Country Estate in Center of C’Town
A kitchen with wooden cabinets, a stainless steel refrigerator, a coffee maker, and a water dispenser.

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, (43 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.
$292 nightly
The price is $333
Nov 2 - Nov 3
Total with taxes and fees
Large 2 bedroom house with private parking in a nice neighborhood
Stylish kitchen with open layout and island seating

11. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (8 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
Oct 25 - Oct 26
Total with taxes and fees
Pool Loft Suite | Bay Access & Beach Passes
A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with bar stools.

12. 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, (28 reviews)
"Lovely place to stay. Very nice area and the host was very accommodating."
United States
Jax H.
$183 nightly
The price is $208
Oct 28 - Oct 29
Total with taxes and fees
Cute, Cozy 2-bedroom house near Annapolis with water access
A living room with a sofa, a coffee table, a dining table with chairs, a lamp, and a beach-themed artwork on the wall.

13. 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
$91 nightly
The price is $104
Oct 26 - Oct 27
Total with taxes and fees
Lower Level Loft - Adorable Studio Apt. Near BWI
Aft deck with spiral staircase to the rooftop, sliding glass doors, and an unobstructed sunset view across the Magothy River from Ferry Point Marina.

14. 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, (13 reviews)
"Beautiful location! Amazing restaurant down the street. Best crab dip and cream of crab soup you’ll ever have."
United States
Anonymous traveler
$312 nightly
The price is $356
Oct 28 - Oct 29
Total with taxes and fees
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
A narrow hallway with wooden flooring, a white door, and a mirror on the wall.

15. Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio
Fells Point
9.8 out of 10, Exceptional, (100 reviews)
"Awesome place, great location"
United States
Mark M.
$195 nightly
The price is $225
Oct 26 - Oct 27
Total with taxes and fees
Hidden Fells Point Gem / Private Courtyard Patio
A waterfront with docked boats, a water taxi, and historic buildings.

16. 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
$197 nightly
The price is $228
Oct 28 - Oct 29
Total with taxes and fees
Cozy Fells Point Gem / In The Heart of Fells Point
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 a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (56 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
$259 nightly
The price is $278
Oct 26 - Oct 27
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
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.
$505 nightly
The price is $575
Oct 25 - Oct 26
Total with taxes and fees
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
A cozy cabin interior with a leather sofa, a wooden dining table, and a view of a lake through large windows.

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

The Hideaway Spot- Waterfront w/ Dock on Long Cove
Glen Burnie
9.2 out of 10, Wonderful, (17 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.
$331 nightly
The price is $378
Oct 27 - Oct 28
Total with taxes and fees
The Hideaway Spot- Waterfront w/ Dock on Long Cove
A wooden dock with Adirondack chairs and a ladder, overlooking a calm body of water with a distant shoreline.

20. 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.
$583 nightly
The price is $665
Oct 26 - Oct 27
Total with taxes and fees
Chesapeake Cottages- 2 Quaint Waterfront Retreats
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

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Easy access to downtown, Great waterside restaurants."
John 1-night trip
Posted 10 hours ago
Annapolis Waterfront Hotel, Autograph Collection

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 $154 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?

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.