Rock Hall Holiday Rentals

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Holiday Rentals in Rock Hall

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (50)
"Wonderful quiet night in Rock Hall. Quick walk to Blue Heron Oyster for dinner. "
The price is NZ$508
includes taxes & fees
13 Oct - 14 Oct
BAYSIDE BUNGALOW

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

10.0 out of 10, Exceptional, (57)
"We had an awesome time at the property. The pool and jacuzzi are great for the family to play together. The house has board games and toys for the little ones, plus bikes to explore the little town. We will definitely be back. "
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

Charming cottage with Pool Access and WiFi in lovely Rock Hall

10.0 out of 10, Exceptional, (3)
"Wonderful 2 night stay at this charming cottage in Rock Hall. We would definitely recommend. "
Charming cottage with Pool Access and WiFi in lovely Rock Hall

Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD

9.8 out of 10, Exceptional, (64)
"Had such a great time at this cottage...would definately come back! Close to downtown activities and easy walking to water. Enjoyed our time there!"
Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

10.0 out of 10, Exceptional, (15)
"A very well maintained and comfy apartment that is just a short walk to the heart of Rock Hall. My family especially enjoyed the large private backyard. Rick made sure we had everything we needed."
The price is NZ$499
includes taxes & fees
1 Oct - 2 Oct
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Waterfront Paradise on the Eastern Shore of Chesapeake Bay

10.0 out of 10, Exceptional, (72)
"We had truly the most amazing stay. The house is set up beautifully for multiple families, so much indoor and outdoor space to spread out and enjoy. The kitchen extremely well stocked, we easily prepared a handful of large meals over the course of our stay and found everything we needed and more. The pool, grounds, and little bay beach had us pretty constantly outside even when the weather was not ideal. So close to Rock Hall and all that there is to enjoy in that idyllic small town. Gunner made...
Waterfront Paradise on the Eastern Shore of Chesapeake Bay

Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

10.0 out of 10, Exceptional, (7)
"Great house everything you need plenty of room convenient to rock hall and tolchester, will stay again "
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

9.6 out of 10, Exceptional, (120)
"Always a great stay at the John Bruff house! Location is perfect, great view of the harbor and even saw a free concert in the park!!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (36)
"Fabulous place. We’ll be booking again next year. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (39)
"We really enjoyed our stay. Looking forward to staying again!"
Cass-N-Reel Luxury Houseboat

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (233)
"This was a wonderful historic home to vacation in"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

10.0 out of 10, Exceptional, (13)
"The host was amazing. The property was as described and was perfect for our group. "
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Waterfront Getaway, Dock Your Boat & Play!

10.0 out of 10, Exceptional, (2)
"Lovely stay, don't let the RV aspect.of it scare you. Nicer than most other bnbs ice stayed in. Quiet, clean and beautiful view of the water. "
The price is NZ$549
includes taxes & fees
1 Oct - 2 Oct
Waterfront Getaway, Dock Your Boat & Play!

Floating 2 bed 2 bath condo stunning views of the bay

2.0 star property
6.8 out of 10, (5)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. "
Floating 2 bed 2 bath condo stunning views of the bay

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

9.4 out of 10, Exceptional, (14)
"Our group had a great time! This house was super convenient location and easily walkable to Main Street. Thank you!"
The price is NZ$2,147
includes taxes & fees
13 Oct - 14 Oct
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

10.0 out of 10, Exceptional, (193)
"We all had wonderful stay at Love point! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

Large 2 bedroom house with private parking in a nice neighborhood

9.4 out of 10, Exceptional, (28)
"This place was perfect place to stay while visiting the area. Everything was clean and the location was great for visiting Annapolis. Will stay again when we are back out this way."
The price is NZ$567
includes taxes & fees
1 Oct - 2 Oct
Large 2 bedroom house with private parking in a nice neighborhood

Luxury Parkfront Haven with Hot Tub - Beloved by Families & their Dogs

9.8 out of 10, Exceptional, (64)
"Cute and quiet neighborhood with a beautiful view of the park. The host made it a stress free stay with great tips."
The price is NZ$490
includes taxes & fees
13 Oct - 14 Oct
Luxury Parkfront Haven with Hot Tub - Beloved by Families & their Dogs

Luxury Waterfront Executive Family Home Annapolis with All Amenities

7.4 out of 10, Good, (3)
"Very beautiful, uniquely designed home on the water. There were 2 bedrooms on the first floor making in it easy for our elderly quests. The main suite was great for our young adults to stay in together with 2 kings, sectional and multiple love sacs. Plenty of seating throughout the home both inside and out. "
Luxury Waterfront Executive Family Home Annapolis with All Amenities

Charming townhome with AC and WiFi in delightful Annapolis

4.0 out of 10, (1)
"This is a room, property owner will be there during your stay. Mattress on The floor. Single pillow, comforter, no top sheet. No curtans, and in a mildly questionable part of town. Owner was very "
The price is NZ$199
includes taxes & fees
2 Oct - 3 Oct
Charming townhome with AC and WiFi in delightful Annapolis
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

Find out more about Rock Hall

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, 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 NZ$199 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 close to the most popular sights in Rock Hall, 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?

BAYSIDE BUNGALOW: This highly rated holiday home rental in Rock Hall is equipped with a patio, air conditioning and WiFi to help you feel comfortable during your stay. Kitchen amenities include a fridge, a microwave and a coffee maker. Another good choice for your trip to Rock Hall is Waterfront w/private pier, pool, Hot Tub, kayaks and in town..

How many holiday rentals are there in Rock Hall?

Choose from 43 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 Ferry Park are a couple of picturesque spots to enjoy the outdoors. In the wider area, you’ll find Rock Hall Harbor and Love Point State Park.

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.