Sudlersville Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Sudlersville

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, 36 reviews
"Waterview cottage is comfortable and very clean. The accommodations look new and we had good sleep. The kitchen has most of the necessary equipment for meal preparation. A baking sheet pan is needed. WiFi and Roku TV was excellent. The primary bedroom bed was so tall/high my wife could not get in or out of it. That necessitated sleeping in the 2 twins. Plus, one of the twins was missing the top mini mattress. The view is mostly of the neighborhood street, nearby homes and their roofs and a small...
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, 18 reviews
"This is a excellent cottage for a short getaway. As the listing states, the cottage is small so only big enough for 1-2 people. There is a nice refrigerator and microwave to heat things up but no facilities for cooking. Paul and Chris are very friendly and helpful. Their dog Vinny is also friendly. We came for a triathlon and the porch was a covered so we could keep our bikes there. The sauna was also great to use after our triathlon."
The price is NZ$444
per night
16 Jun - 17 Jun
BAYSIDE BUNGALOW
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
10.0 out of 10, Exceptional, 20 reviews
"Cozy & elegant ☀️ a clean bright space."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
9.8 out of 10, Exceptional, 15 reviews
"My friends, our wives, and kids loved our stay. Everything exceeded expectations. We especially enjoyed the backyard where we played yard games, grilled, and enjoyed the river."
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
200 steps to the beach!
10.0 out of 10, Exceptional, 77 reviews
"Cute cottage very close to the beach. We had everything that we needed for our mini vacation. Very clean and well taken care of cottage."
200 steps to the beach!
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
10.0 out of 10, Exceptional, 28 reviews
"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
Secluded Waterfront Cottage on 200 acre farm near Queenstown
10.0 out of 10, Exceptional, 90 reviews
"We enjoyed meeting the hosts and their llamas and emus. The home had everything we needed for our stay, and the view of the water from the house could not be better. We watch the sunsets wherever we go, and the colors were spectacular. There were plenty of things to do, and the restaurants were a short drive away. Thank you for sharing this property with others."
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Rambling Victorian Beach House on Maryland's Eastern Shore
10.0 out of 10, Exceptional, 13 reviews
"Our group of couples + kids enjoyed our getaway to the Eastern Shore. Betterton was a great home base to visit our alma mater, Washington College, in Chestertown. There, we visited the farmers market and waterfront park & playground with the kids. Back in Betterton, the house fit our group well. Plenty of bedrooms, bathrooms and space for each family. The kids & adults enjoyed spending time lounging in the third floor living room. We were pleased that the house had plenty of games, kids toys,...
Rambling Victorian Beach House on Maryland's Eastern Shore
Family-Friendly Cottage, Walk to the Beach!
10.0 out of 10, Exceptional, 14 reviews
"Great location "
Family-Friendly Cottage, Walk to the Beach!
First Floor Studio Apartment in Historic Chestertown
9.8 out of 10, Exceptional, 60 reviews
"It was a nice room in a nice neighborhood. Only complaint would be the coffee maker was awful."
The price is NZ$268
per night
17 Jun - 18 Jun
First Floor Studio Apartment in Historic Chestertown
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
9.6 out of 10, Exceptional, 4 reviews
"Tv channels were sparse"
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |
10.0 out of 10, Exceptional, 3 reviews
"Wonderful rental home for our family with great pool and river view. Swimming every day in the pool was so much fun for everyone, kayaks, and paddle boards were great since we did not have to bring anything. Children fished every night on the dock. We played lots of games inside and out everyday and enjoyed the Nature all around to see, birds, deer, fish, frogs and small animals. Our family felt like they had their own getaway for a wonderful vacation. Thank you for everything."
Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |
Eastern Shore beach cottage get-away
10.0 out of 10, Exceptional, 123 reviews
"The property was clean and perfectly located across from the Chesapeake Bay. We enjoyed our stay and will definitely book it again!"
Eastern Shore beach cottage get-away
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC
10.0 out of 10, Exceptional, 2 reviews
"Couldn’t have asked for a better place for us. Lots of room and quiet neighborhood."
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC
Peaceful getaway convenient to local amenities including beach, boating & food
9.8 out of 10, Exceptional, 104 reviews
"We were there for the local triathlon weekend. This property was centrally located within easy walking distance to the water, race site, and restaurants. We didn't get much of a chance to explore downtown but still had a great time relaxing and talking to the locals!"
Peaceful getaway convenient to local amenities including beach, boating & food
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
10.0 out of 10, Exceptional, 40 reviews
"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.
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
9.8 out of 10, Exceptional, 80 reviews
"House was fine. Odd they did not provide sheets. Was difficult for folks who came from far away. But the house was lovely and we enjoyed our time there!!"
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
Private pier and pool at this waterfront Chestertown home
9.8 out of 10, Exceptional, 22 reviews
"We stayed at Peir Pleaseure for Washington college homecoming weekend. We had a BBQ by the pool for our son and his friends. We enjoyed the views of the Chester Riiver from the pier. The house was clean and easiliy accomodates 2 families ."
Private pier and pool at this waterfront Chestertown home
Grasonville Home w/ Private Pool on the Water
10.0 out of 10, Exceptional, 14 reviews
"We had a wonderful time in Grasonville. The property was very clean and well maintained. Views from the home were serene as most rooms have views of the water which we absolutely loved. Another perk of the home is its proximity to surrounding attractions. Our group felt like we were secluded enough but could easily get something in town if needed. We didn’t need much since the home was well stocked. When we contacted the host about a question, they responded quickly. We would definitely stay...
Grasonville Home w/ Private Pool on the Water
Home away from home
7.6 out of 10, Good, 5 reviews
"Nice place to stay for quick weekend. Close to everything."
Home away from home
Don't see what you're looking for?
See all available properties in Sudlersville
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 Sudlersville you may be interested in

Bally's Dover Casino Resort
4.0 star property
8.6 out of 10, Excellent, 1,388 reviews
"I liked the Price."
The price is NZ$153
per night
1 Jul - 2 Jul
Bally's Dover Casino Resort
Microtel Inn & Suites by Wyndham Dover
2.0 star property
8.0 out of 10, Very good, 1,003 reviews
"Very clean, nice room, nice staff. Nice breakfast "
The price is NZ$157
per night
17 Jun - 18 Jun
Microtel Inn & Suites by Wyndham Dover
Red Roof Inn & Suites Dover Downtown
2.5 star property
7.4 out of 10, Good, 1,004 reviews
"This was a very clean and comfortable place to stay. Extra bonus that they do not charge for pets. Staff was friendly and helpful. I would definitely recommend this place "
The price is NZ$144
per night
24 Jun - 25 Jun
Red Roof Inn & Suites Dover Downtown
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 Sudlersville 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 Sudlersville. 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 Sudlersville. Seeing all the best attractions is bound to make you fall in love with Sudlersville. 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 Sudlersville short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Sudlersville?

Yes, there are holiday rentals close to the most popular sights in Sudlersville, or you can select a more secluded option if you're looking for a relaxing stay. Sudlersville is known for its wineries.

What are some of the best holiday rentals that Sudlersville has to offer?

Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.: This holiday home rental outside of Sudlersville is located on the waterfront, and has a private balcony, a private garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

What can I see and do in Sudlersville?

While exploring the area, visit family-friendly sights like Crumpton Auction, or get outside and enjoy nature at Betterton Beach. Tilmon's Island Winery and Rolphs Wharf Marina are a couple of places you'll find in the wider area.

What are holiday rentals like in Sudlersville?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Sudlersville. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from public hotel lifts and busy front desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for a family trip or a small group gathering.

Recent reviews of Sudlersville properties
Expedia verified reviews