House vacation rentals in Rock Hall

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Popular amenities for Rock Hall house rentals

House rentals with a pool

Top guest favorite
Home in Chestertown
5 out of 5 average rating, 24 reviews

Chestertown Watson Family Farm

AmyRating, 5 stars2 days ago
Words can’t describe how incredible this home/property is! You have the option to just sit by the water or in the hammock watching the birds play and fish jump, or you can do one of the MANY activities Molly has provided for you. Kayaks, canoes, paddle boards, pickleball, yards games, pool activities, etc are all provided. The family room is all windows so it not only provides the most incredible breeze- it is great for enjoying all the sights even if you’re not outside in it. Inside there are tons of toys for kids- you do not have to bring a thing if you have kids. They have inside toys, outside toys, kids life jackets, goggles, water balloons, rafts, floaties, pack and play…. Molly and her family have thought of it ALL. We are already talking about coming back. Molly was the best host- responsive, helpful and inviting.
Superhost
Home in Edgewater
4.91 out of 5 average rating, 147 reviews

House in Edgewater Maryland

CarmenRating, 5 stars1 week ago
It was amazing.The pool is so fun.We had bad weather but we were still a little inside.The location is quiet and beautiful. We will come back for sure. Thank you
Superhost
Home in Queenstown
4.81 out of 5 average rating, 157 reviews

Bay Breeze Retreat

TobyRating, 5 stars1 month ago
Fabulous views of Chesapeake Bay, pool was great, deer everywhere, house was spacious with three living areas. Would definitely stay there again.
Guest favorite
Home in Rock Hall
4.95 out of 5 average rating, 38 reviews

Rockfish Keeper

Mary JaneRating, 5 stars1 month ago
It was a great stay after a long day roaming around Washington DC and Maryland. The accommodation was clean and nicely decorated with very inspiring words of wisdom providing a cozy and comfortable retreat throughout our stay. Kelly has been very informative and detailed on the instructions to help us on a very smooth check in and check out process. The location was fantastic and quiet neighborhood. Overall, we had a wonderful time and would highly recommend this place to anyone looking for a memorable Airbnb experience!"
Top guest favorite
Home in Rock Hall
5 out of 5 average rating, 15 reviews

The Mariner's House

ErinRating, 5 stars1 month ago
Wonderful property with lots of amenities!
Guest favorite
Home in Severn
4.88 out of 5 average rating, 170 reviews

Large Home with Pool & 7 bedrooms; sleeps 21

SamihahRating, 5 stars2 weeks ago
This home was the perfect place to celebrate my daughter’s graduation! We had family travel in from several states, and everyone felt comfortable and truly enjoyed the spacious layout. It was a bit too chilly to use the pool, but I’m already looking forward to booking this home again. I’ll definitely be a repeat renter!
Guest favorite
Home in Fort Washington
4.92 out of 5 average rating, 156 reviews

5 BEDR, Inground Pool+Billiard Table, Close To D.C

TheresaRating, 5 stars1 week ago
Daniel’s Home was beautiful and he made this special event for me and my family able to celebrate my sons 26th Heavenly Birthday a success We were very comfortable and it really felt like home the pool was very clean and the Home was very spacious and squeaky clean I would love to Book Daniel again He was a very nice and friendly Host that responded to any questions we had he made communication easy me and my family really enjoyed our self and yes he’s reasonable and you definitely get what you paid for and more Thank you again Daniel
Top guest favorite
Home in Kent Narrows
5 out of 5 average rating, 301 reviews

Chester Riverfront At Kent Narrows

CassandraRating, 5 stars3 weeks ago
A great place to enjoy a long weekend at the Eastern shore in Maryland.

Weekly house rentals

Guest favorite
Home in Chestertown
4.93 out of 5 average rating, 45 reviews

Waterfront Paradise w/ Pier - kayak to Chestertown

MaxRating, 5 stars3 weeks ago
This was my second time staying here with my family and dogs. We absolutely love the property and area! We enjoyed kayaking and are dogs enjoyed swimming and playing along the river. Ina was a great host and was responsive to our needs. It was a great experience and vacation!
Guest favorite
Home in Chestertown
4.93 out of 5 average rating, 30 reviews

River Cottage, Chestertown

FranklinRating, 5 stars8 months ago
Beautiful location and the bikes, kayaks and fire pit all added fun and relaxation to our stay! Close enough to Chestertown to enjoy the farmers’ market and shopping and far enough out to be a peaceful retreat.
Guest favorite
Home in Rock Hall
4.9 out of 5 average rating, 30 reviews

Spacious Victorian close to everything in RH!

LisaRating, 5 stars4 weeks ago
Lovely immaculately clean home close to rock hall marinas. The beds were really comfortable and hosts super responsive. Loved all the books and board games they had. Kitchen very well stocked. Highly recommend staying here.
Top guest favorite
Home in Pasadena
5 out of 5 average rating, 17 reviews

Rock Creek Cottage, Waterfront

JaneRating, 5 stars2 days ago
We loved this place! Perfect location for our festivities in Pasadena and very peaceful.
Guest favorite
Home in Chestertown
4.96 out of 5 average rating, 25 reviews

Lotus House: porches, decks, yard, beach access

JamesRating, 5 stars4 months ago
House was beautiful, clean and host was phenomenal. Highly recommend!
Top guest favorite
Home in Chestertown
4.95 out of 5 average rating, 73 reviews

Waterfront w/ Hot Tub + Dock | Harbor View Haven

AmyRating, 5 stars3 weeks ago
Perfect place to relax and celebrate our daughter’s graduation. Would definitely stay there again! Thank you for sharing your home with us!
Superhost
Home in Rock Hall
4.94 out of 5 average rating, 35 reviews

Rock Hall Sharp Street Retreat

MicheleRating, 5 stars3 weeks ago
We had a great stay in Rock Hall at Rick’s place for our triathlon race weekend. The house was very clean in a quiet neighborhood. It has a fully equipped kitchen and stocked with extra toiletries; which is always helpful. It’s located in a lovely area by the water with great local restaurants and shops. Communication with Rick was excellent and he’s a very responsive and helpful host.
Guest favorite
Home in Rock Hall
4.89 out of 5 average rating, 38 reviews

Bayside cottage steps from the harbor

Emily Catherine TaylorRating, 5 stars8 months ago
This rental is a total gem! Think of the standard expectation for a good rental, then level up. That's what they did for every detail. They somehow managed to have everything you need to feel comfortable, but had zero clutter. It felt like they really wanted us to have an enjoyable experience. The house is any easy bike ride to Rock Hall's charming downtown and a quick walk to Watermans Crab House, which has many delicious offerings and gorgeous outdoor dining. Rock Hall itself is pretty remote. They have several good restaurants and a decent grocery market, which is more than can be said for most of the other towns in this area. If you're looking to be off the beaten path, you'll love it here.

Private house rentals

Top guest favorite
Home in Middle River
5 out of 5 average rating, 18 reviews

Waterfront Paradise on Seneca Creek w/Hot Tub

FeliciaRating, 5 stars1 week ago
Nicki was an exceptional host—responsive, thoughtful, and truly dedicated to providing a wonderful experience. The home was absolutely stunning, equipped with everything we needed, and her attention to detail was impressive. She truly thought of everything, making our family trip seamless and memorable. The property was in pristine condition—immaculately clean, set in a peaceful and quiet location with breathtaking views. I honestly can't say enough great things about this home! As a Realtor, I will be recommending it to all my clients, family, and friends. We can't wait to rebook our stay there again soon!
Guest favorite
Home in Stevensville
4.97 out of 5 average rating, 34 reviews

Spacious4BR home with waterviews

GaryRating, 5 stars1 month ago
5 adults, 2 children under age 6 stayed at Courtney's home, which was just as described and pictured on the airbnb web page. Great location for our stay for wedding weekend; very comfortable furniture (sofas, chairs, beds; many amenities provided for guests; terrific well-stocked kitchen; very large screened-in porch w/ nice view of Chesapeake Bay and surroundings; spacious bedrooms; 4 full bathrooms; very clean when we arrived. I could go on .... Courtney is a very good communicator, and responded quickly to the few questions we really had. She is a great host and the house was terrific for our needs.
Top guest favorite
Home in Joppatowne
5 out of 5 average rating, 33 reviews

Two bedroom small ranch with beautiful forest view

JosefinaRating, 5 stars2 days ago
This listing was immaculately clean, beautifully decorated and very organized. The area was quiet and beautiful. Neighbors in the area very nice. They offered all the basic and necessary amenities needed and more. Our overall experience was GREAT and we definitely would rent this location again.
Top guest favorite
Home in Grasonville
5 out of 5 average rating, 59 reviews

Bay Breeze - 3BR Waterfront Chester River Retreat

BrianRating, 5 stars2 days ago
Stayed at Katie's place for a long weekend getaway with my family and a couple of friends. We all loved the house, its location, and the beautiful and relaxing waterfront views. The house was pristine and beautiful. We all would love to go back again. Thank you Katie for offering up your lovely home and looking forward to potential future trips there!
Guest favorite
Home in Crownsville
4.93 out of 5 average rating, 15 reviews

Welcome to Heron House! Annapolis Waterfront Oasis

HaleyRating, 5 stars1 week ago
We had the best time enjoying Jody and Gail's beautiful home! The views were incredible, it was so peaceful, and the house had every amenity we could have wanted. A highlight was kayaking and swimming in the cove right to the side of the home. We cant wait to come back!
Top guest favorite
Home in Chestertown
5 out of 5 average rating, 42 reviews

In Town Chestertown Rancher (1 Block to College)

KatieRating, 5 stars1 week ago
Tim’s house was perfect for our group of 4 adults and 4 kids. It’s very cute, clean, and spacious. His level of hospitality did not go unnoticed, he seemed to of thought of everything. The kitchen was well equipped for cooking if you choose to do that. We would definitely stay here again!
Guest favorite
Home in Chester
5 out of 5 average rating, 9 reviews

Kent Island Escape

Maggie Rating, 5 stars1 week ago
We stayed at this beautiful airbnb during the transition of our house selling locally. It was a beautiful place to stay during our transition. Definitely come be a place to stay at again.
Top guest favorite
Home in Annapolis
5 out of 5 average rating, 42 reviews

Bay Home in Annapolis with Private Dock

ToddRating, 5 stars3 weeks ago
Beautiful place, beautiful location. Joel thought of anything you could want.

Quick stats about house rentals in Rock Hall

  • Total rentals

    20 properties

  • Total number of reviews

    680 reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Wifi availability

    20 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

  • Local attractions

    Waterman's Crab House, Harbor Shack, and Osprey Point Inn

Destinations to explore

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  3. Maryland
  4. Kent County
  5. Rock Hall
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