Rock Hall Vacation Rentals

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Browse Select Rock Hall Vacation Homes

Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
10.0 out of 10, Exceptional, (5)
"This property is a gem! Close to everything but without too much hustle or bustle! Great amenities. Kimberley is very easy to work with and graciously accommodated my need for late check out. Parking is private and off street!"
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
10.0 out of 10, Exceptional, (44)
"Second year staying in On the Rocks! The family had a great time again. Easy walks in the morning for coffee at Java Rock. Great seafood at plenty of restaurants. We all enjoyed the pool, kayaking and bike rides but the best part is the views and sunsets. We also enjoyed the fire pit each night after the kids went to bed. Great family vacation spot. "
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Walk to Everything House
10.0 out of 10, Exceptional, (67)
"We enjoyed this lovely historic home that is a short walk to attractions in St Michaels. It has a nice patio out back and is very close to a coffee shop."
Walk to Everything House
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
10.0 out of 10, Exceptional, (5)
"Our stay here with Brenda was amazing! She was very pleasant and professional! She even suggested a few things for us to do in the area. The home had everything we could have needed and wanted. The place looks even better in person than the pictures! We can’t wait to book again!"
The price is CA $237
CA $450 total
includes taxes & fees
Sep 23 - Sep 24
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
River Front, Private Single Family Home
10.0 out of 10, Exceptional, (4)
" If I could give a 10 star rating I would! Host was very responsive to inquiries. Place was clean and peaceful. Tucked away in its little community, yet minutes to anything you could need or want. Pictures are accurate. The view is beautiful. Would definitely book again. "
River Front, Private Single Family Home
Waterfront Cottage on the Eastern Shore
9.6 out of 10, Exceptional, (7)
"We rented the house for the weekend and to host a surprise birthday party. We had the party right at the beach and the host/concierge were able to help us with everything we needed. They really went out of their way for us, and it made a huge difference in the party’s success! Plus, you can’t beat the view and the Chesapeake Bay sunsets !!"
The price is CA $474
CA $1,111 total
includes taxes & fees
Oct 3 - Oct 4
Waterfront Cottage on the Eastern Shore
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
10.0 out of 10, Exceptional, (96)
"We took a quick weekend getaway to Annapolis. It was our first time there and we loved it. The location of the house is perfect. We were so close to the bay with tons of restaurants nearby. It was a quiet neighborhood though so we didn’t feel like we were in a party scene. The house was so clean. The pool was huge (bigger than expected), and the host went above and beyond. Liz was an excellent communicator. She had more than enough essentials at the house that made our stay so relaxing. I felt...
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (29)
"Perfect for a 3 day visit! "
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Dollhouse in Central Historic St Michaels
9.6 out of 10, Exceptional, (44)
"This is a lovely historic home that is close to town. It's nicely decorated, has a screened deck out back, and makes for a comfortable stay."
Dollhouse in Central Historic St Michaels
CHeerful 3-bedroom waterfront home
10.0 out of 10, Exceptional, (29)
"Coming from Las Vegas the weather was such a great relief and we enjoyed our coffee every morning on the outside patio. We love to fish and enjoy water views... We fished off the dock and caught crabs in crab cages every day!! The home was very clean and well stocked. Beds were extremely comfortable and kitchen has modern appliances. We enjoyed the fire pit also. Great for families both young and old. Host was very easy to communicate with and very accomodating. Highly recommend!!"
CHeerful 3-bedroom waterfront home
Trendy Spot in Downtown Baltimore/Fells Point
10.0 out of 10, Exceptional, (8)
"Was in for a weekend getaway and the place was a described. Plenty of space and privacy for the 8 of us. Just a little short walk to the center of Fells Point. Amoni was accessible all weekend long regardless of the time of day. We thoroughly enjoyed our stay. Would stay with Amoni again."
Trendy Spot in Downtown Baltimore/Fells Point
Serene waterfront home with kayaks, paddle board, grill, firepit, W/D, and AC
9.8 out of 10, Exceptional, (6)
"Where do I even start with how GREAT this rental was. Everything from start to finish was exceptional. When we arrived, getting into the house was no issue at all. It was exactly per the instructions we received for check in. We walked into the IMMACULATELY clean house and couldn't believe it. I mean, not a spot of dirt to be seen. We arrived later in the evening so explored the house and then went to bed in extremely comfortable beds. So comfortable that we looked at the mattress type to...
Serene waterfront home with kayaks, paddle board, grill, firepit, W/D, and AC
Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis
10.0 out of 10, Exceptional, (89)
"It was nice to get outside DTA and see another part of Annapolis. 15 minutes from DTA it was quiet and beautiful small cottage perfect for our family. The home was clean and designed well. We would stay again. Thank you!!!"
Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis
Close to US Naval Academy, downtown Annapolis, Maryland Live Casino, BWI Airport
10.0 out of 10, Exceptional, (14)
"Property is well maintained and very clean. Great location for airport, DC and Annapolis. Only suggestion is to add a coffee pot. One cup at a time was a little annoying at breakfast."
Close to US Naval Academy, downtown Annapolis, Maryland Live Casino, BWI Airport
Nautical charmer near the City Dock with open layout, W/D, & AC
10.0 out of 10, Exceptional, (5)
Nautical charmer near the City Dock with open layout, W/D, & AC
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!
10.0 out of 10, Exceptional, (12)
"Family gathered for the weekend to celebrate our parents/grandparents who both recently passed this year. They owned a house in Rock Hall for 25 years, where we had regular family gatherings, giving us so many fond memories. The weekend was bittersweet as we returned to Rock Hall for the first time in years. The house was lovely, cozy, has a great deck, fire pit and shed with well taken care of bikes and games. It was clean and beds were comfortable. We would stay there again. Thank you for...
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!
Johns Hopkins Historic Renovated home - Location!
10.0 out of 10, Exceptional, (6)
"The property is very well maintained, pleasant welcoming atmosphere. One would hardly tell if neighbors existed due to the peaceful environment. Anybody wishing to stay here should not think twice, JUST GO FOR IT"
The price is CA $186
CA $469 total
includes taxes & fees
Sep 23 - Sep 24
Johns Hopkins Historic Renovated home - Location!
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
2.5 star property
10.0 out of 10, Exceptional, (4)
"Cannot recommend enough! Lauren was so sweet and accommodating. The home is gorgeous and filled with so much charm. Perfect location. An absolute 10/10! "
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
Charming 3-bedroom house in Annapolis ⚓️🛥️⛵️ on the Chesapeake Bay
8.0 out of 10, Very good, (1)
"The house was quiet, cozy and fit our needs perfectly. The location was convenient for our trips to and from DTA. Our host, Abber was available for any questions we had and made our stay enjoyable. "
Charming 3-bedroom house in Annapolis ⚓️🛥️⛵️ on the Chesapeake Bay
Pet-Friendly Annapolis Home: Walk to Beach!
Pet-Friendly Annapolis Home: Walk to Beach!
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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.
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Other property types in Rock Hall

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
10.0 out of 10, Exceptional, (44)
"Second year staying in On the Rocks! The family had a great time again. Easy walks in the morning for coffee at Java Rock. Great seafood at plenty of restaurants. We all enjoyed the pool, kayaking and bike rides but the best part is the views and sunsets. We also enjoyed the fire pit each night after the kids went to bed. Great family vacation spot. "
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
10.0 out of 10, Exceptional, (29)
"Ideal vacation for family of 22. It suited everyone."
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
10.0 out of 10, Exceptional, (21)
"Perfect choice for our group. 2 adult couples in the house and our son, his wife and 2 small children in the detached suite. Impressive water pressure in the shower!!! Wish we had time to stay longer. Quiet neighborhood, very relaxing. "
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
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.