Rock Hall Holiday Rentals

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Holiday Rentals in Rock Hall

Interior
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
9.8 out of 10, Exceptional, (14)
"We really enjoyed our (much too short) stay at this waterfront gem!! The property was very clean, had all the amenities that we needed for our time away.... the only complaint is that we didn't have enough time to enjoy it all!! : ) thank you so much, we will be back!"
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Balcony
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
10.0 out of 10, Exceptional, (28)
"I organized a large (15 person) bachelorette weekend at this property in early April. It is an absolutely gorgeous house and the host had a number of thoughtful touches - like extra firewood for the firepit, coffee supplies, and a bottle of bubbly for our bride! The beds were comfortable (even the twins!), which was lucky because one bedroom on the breakdown was not really usable, so a handful of guests relocated to one of the 'kid rooms.' We found Ashleigh very responsive both before and...
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Balcony
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
10.0 out of 10, Exceptional, (40)
"Beautiful property. Needs better towels and linens. Kitchen is well equipped. Living areas are spacious and comfortable"
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
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Fridge, microwave, stovetop, dishwasher
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
10.0 out of 10, Exceptional, (41)
"This house was beautiful, clean, modern, everything we needed. Loved the huge table and living-room areas where all of us could be together. Weather wasn't great, so we didn't do anything outside, but the house alone was perfect. Host responded quickly, kitchen was fully equipped. Will definitely consider for our next stay!"
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (4)
"Wonderful place to stay and Erin was great. Asked about a Grill on the property and the next day we had a grill. The young adults loved the pool and water activities while the older adults enjoyed sitting on the docks watching the sunrise with a cuppa coffee. Would highly recommend this property."
The price is NZ$2,304
includes taxes & fees
4 Jun - 5 Jun
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Fridge, microwave, oven, stovetop
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (180)
"Charming spot in the heart of Annapolis, just a few moments walk from anything you might need."
Directly Across from Gate One & Steps from the Waterfront
Exterior
The Heron's Nest at Atlantic Marina
10.0 out of 10, Exceptional, (265)
"Adorable cabin with an excellent view."
The Heron's Nest at Atlantic Marina
Exterior
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (186)
"The cottage is fully stocked, clean, and cozy. We thoroughly enjoyed sitting on the deck and watching all the wildlife."
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (26)
"The stay was a perfect location for doing things in downtown St. Michael's, everything is within walking distance. The property managers were prompt with all communications and pleasant to work with on a few questions I had."
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Property grounds
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, back yard fun
10.0 out of 10, Exceptional, (61)
"We had a great stay here for my husband’s birthday. Pat and Ken were fantastic hosts and even decorated for this birthday. They provided everything we would need for our toddler and if the weather had cooperated we’d have spent hours and hours in the backyard. Really appreciative of all the attention to detail and would highly recommend this listing if you’re looking for a low-key, relaxing stay where you don’t need to worry about the details."
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, back yard fun
Fridge, microwave, oven, stovetop
Recently Renovated Annapolis Home - Conveniently Located
10.0 out of 10, Exceptional, (44)
"This house was perfect for a group of friends celebrating a 50th birthday! The house was so clean and well cared for! The front porch and outdoor backyard space provided even more room for us to gather together. We will be back!"
Recently Renovated Annapolis Home - Conveniently Located
Pool
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (51)
"Beautiful and huge property. Paddling in the river was great!"
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Beach
Cozy place close to the city dock
10.0 out of 10, Exceptional, (54)
"It is a very nice home for our short stay. We came for a graduation ceremony and the convenience and location were perfect. We will stay here in the future."
Cozy place close to the city dock
Outdoor pool
Pool and Bay Views on wrap around deck in Kent Island
9.6 out of 10, Exceptional, (21)
"Everyone really loved the house and the location. The pool was great"
Pool and Bay Views on wrap around deck in Kent Island
'At Fells Point' CitySide - 'Tons better than a hotel!'
9.8 out of 10, Exceptional, (161)
"This had everything we needed and Fells Point is a nice area!"
The price is NZ$349
includes taxes & fees
3 Jun - 4 Jun
'At Fells Point' CitySide - 'Tons better than a hotel!'
Private kitchen
Milton Manor: W/D, WiFi, Free Street Parking
2.0 out of 10, (2)
"Good day! I want to first start off by saying thank you for allowing us to stay in your place. However, I do have so things I want to bring to you attention before I leave a review. 1) There is only one Tv in thee entire place when there are two rooms. 2) The Tv that is there doesn’t even work. 3) The sink doesn’t drain and had old water sitting in it. So, we had to brush our teeth in the shower. 4) Very noisy area. Cars come by all day and night. The neighbors above are very loud not to mention...
The price is NZ$351
includes taxes & fees
3 Jun - 4 Jun
Milton Manor: W/D, WiFi, Free Street Parking
Property grounds
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (105)
"Loved this historic house! Perfect location, peaceful neighborhood and walking distance to entire town."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Fridge, microwave, oven, stovetop
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
10.0 out of 10, Exceptional, (81)
"This is an absolutely fantastic place to stay!! The host Liz was so easy to work with and quick to respond to any inquiries we had. We booked for the Herndon climb (#plebenomore) and cannot say enough about how perfect this house was for us. It was an easy walk to DTA and gate #1. The kitchen was well stocked and had everything needed to make several home cooked meals for our son and his friends. The sun room is beautiful and the perfect spot to enjoy a cup of coffee or breakfast! The pool was...
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Property grounds
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (108)
"VRBO link hasn’t enabled me to communicate with property manger/owner as I’m unable to access account via the VRBO link. I’ve re-registered multiple times now."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Property grounds
Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented.
9.6 out of 10, Exceptional, (18)
"Had a nice stay. We would definitalty book again."
Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented.
Don't see what you're looking for?
See all available properties in Rock Hall
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.

Other types of properties in Rock Hall you may be interested in

Interior
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
9.8 out of 10, Exceptional, (14)
"We really enjoyed our (much too short) stay at this waterfront gem!! The property was very clean, had all the amenities that we needed for our time away.... the only complaint is that we didn't have enough time to enjoy it all!! : ) thank you so much, we will be back!"
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Exterior
Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, (1614)
"Absolutely love these properties and the so-rounding area! Great places to eat and shop all within walking distance. "
The price is NZ$333
includes taxes & fees
16 Jun - 17 Jun
Historic Inns of Annapolis
Lobby
Best Western Plus Hotel & Conference Center
2.5 star property
7.6 out of 10, Good, (1001)
"The property itself was surprisingly very clean. Unfortunately my car sideswiped in the parking lot and none of the staff were helpful. "
The price is NZ$204
includes taxes & fees
16 Jun - 17 Jun
Best Western Plus Hotel & Conference Center
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Rock Hall holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Rock Hall. 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 Rock Hall. 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 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 holiday 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 Rock Hall short-term rentals, that won’t be hard to do.

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?

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.: This highly rated holiday home rental in Rock Hall is located on the waterfront, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Rock Hall?

Choose from 38 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 Washington College.

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.

Recent reviews of Rock Hall properties
Expedia verified reviews

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

5/5 Excellent
"Good area, nice staff"
A verified traveller stayed at Sonesta ES Suites Annapolis
Posted 16 hours ago
Sonesta ES Suites Annapolis