Dorchester County Holiday Rentals

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Top Holiday Rentals Destinations in Dorchester County

" October 11-14, 2024, we rented the “Willoughby” for a family reunion. Let me start out by saying this home is amazing. It looks exactly as pictured based on the website photos. It was even better than I expected. If you are considering this property, I highly recommend booking it! Believe me when I say the Willoughby is a rare gem. The location of the home is perfect and extremely private. The grounds are pristine and the view of the water is breathtaking. The home sits on the Hudson...

"My boyfriend and I needed to get away. This house and location was just what we needed. Beautiful scenery, cozy home. We started a full week and I was sad to go at the end of our trip. We look forward to visiting again in the future! "

"What a wonderful stay we had! The house was so comfortable with plenty of space for everyone to relax and enjoy each other's company. We enjoyed the brisk mornings on the porch and the gorgeous sunsets in the evenings. Very comfortable beds and linens. The scenery and landscape in the area are breathtaking. Every turn provided another incredible view of the water. Fishing Creek is close to so many beautiful, quaint towns along the Chesapeake Bay. Highly recommend!"

"Our vacation on Chesapeake Bay was wonderful. The house was clean and comfortable. It is an older home, but we loved the character and charm. There is a very large yard for playing, bikes and some board games/puzzles that we enjoyed. The island was very quiet so made for a relaxing vacation. The home came with kayaks, and we had a blast kayaking with our 2 and 4 year old on the ocean. I would highly recommend this home for a big gathering or small family like our trip. We felt so rested after...

"This house exceeded our expectations in every way. The kitchen is large and well-appointed, the beds are comfortable, and the peace and quiet is priceless. We enjoyed morning coffee in the sunroom, table tennis in the crab house, sunsets from the dock, and stargazing at the firepit. If you desire peace and quiet this house is a perfect choice!"

includes taxes & fees

2 Dec - 3 Dec

Apartment D: Riverfront Grand | Private kitchen

"Great spot and well appointed. Great communicator. HVAC loud and might consider brighter bulbs in lamps. "

includes taxes & fees

1 Dec - 2 Dec

"Were pleased with the property and surroundings. Very beautiful, ancient trees. Neighborhood was quiet and the river and dock were favorite reading spots. Enjoyed!!!"

"Everything close by!"

"We got every year and stay here, it’s great! "

includes taxes & fees

9 Dec - 10 Dec

"The groomsmen and their families attending my daughter's nearby wedding stayed at this spectacular property. I heard nothing but high praise for its beauty, amenities, and comfort. So glad this all worked out for the dates we needed it for!"

"Excellent experience."

includes taxes & fees

2 Dec - 3 Dec

"very quiet, peaceful, relaxing location. The house had everything we needed. We would definitely stay there again."

"Four of my friends and I stayed at this cute home for a ladies' weekend (two nights) in St. Michaels. We are in our early 40's and all agreed that the location of this home is superb. We walked to dinner each night (Limoncello and Ruse, both great) and enjoyed the wonderful shops in the lovely downtown area. The location of this home cannot be beat if you want to park your car upon arrival and not have a need to use it again during your stay. We had three cars, two of which fit in the driveway...

"We loved everything about the Kent Island House! Would book again in a hot minute"

"beautiful location. outside porch was great"

"We needed a house for a quick stay in Lusby. The hosts have thought of everything to make the stay easy. They communicated ahead of our trip and were easy to work with. "

On the beach, sun-loungers, beach towels

"Beautifully appointed cottage. Literally right on the water. Quiet, serene and relaxing. Loved it and will be back!"

"This lovely home sets in a beautful location. The hosts are available and accommodating. They are definitely available if needed. The house itself is very comfy. All amenities you need are there. "

"Awesome home wnd location! Would stay again!"

"This was a quick getaway for my husband, me, and our 2-year-old grandson. The location of this property is perfect! We could walk over to the waterfront and watch the geese or walk into town for shopping and food. We lost power (a fluke) during our stay, and the owner was extremely responsive and easy to contact. We walked to dinner, and it was back on when we returned. Highly recommend!"

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Find out more about Dorchester County

Everything you need to know about Dorchester County 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 Dorchester County 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 Dorchester County holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Dorchester County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Dorchester County. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Dorchester County 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 Dorchester County holiday rentals we have chosen for you start as low as AU$339 per night. Entering your travel dates in the search wizard you might find even better deals.

How to find incredible deals on Dorchester County rentals

At Expedia, we put the best Dorchester County 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 Dorchester County 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 Dorchester County 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 Dorchester County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Dorchester County Holiday Home Travel Info

Popular accommodation	Dorchester County private holiday homes
Known landmarks	Layton's Chance Vineyard and Winery, Great Marsh Park and Choptank River Lighthouse
International airport	Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional)