Sudlersville Vacation Rentals

Vacation Rentals in Sudlersville

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Beach nearby, sun loungers
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (36)
"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
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Interior
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
9.8 out of 10, Exceptional, (15)
"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.
BAYSIDE BUNGALOW
Fridge, microwave, coffee/tea maker, toaster
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (18)
"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 $175
$272 total
includes taxes & fees
Jun 9 - Jun 10
BAYSIDE BUNGALOW
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WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Fridge, microwave, oven, stovetop
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
10.0 out of 10, Exceptional, (19)
"Cozy & elegant ☀️ a clean bright space."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Eastern Shore beach cottage get-away
Sun loungers
Eastern Shore beach cottage get-away
10.0 out of 10, Exceptional, (122)
"The cozy cottage is perfectly maintained and well equipped. The bay view is as advertised and lovely. The location in Rock Hall is ideal, quiet and convenient to everything. The property manager is responsive and informative. We had a great, relaxing getaway weekend and look forward to returning."
Eastern Shore beach cottage get-away
200 steps to the beach!
Interior
200 steps to the beach!
10.0 out of 10, Exceptional, (76)
"House was beautifully decorated, updated, clean, and as advertised, steps from the beach!!! We had everything we needed for meal prep, including a charcoal grill. Enjoyed grilling fresh fish for dinner one night!"
200 steps to the beach!
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Pool | Outdoor pool
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (52)
"My family of 4 stayed here. So many things to do outside-truly a good time. So many games and accessories to have an easy good time. Would definitely stay at this place again."
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
Property grounds
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
9.8 out of 10, Exceptional, (80)
"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.
Retreat Near Dover
Private kitchen
Retreat Near Dover
10.0 out of 10, Exceptional, (2)
"The location was ideal for visiting with nearby family. It's so nice and comfortable that other out-of-town family has expressed interest in future rental of the home. The only deficit or suggestion would be the ability to use the washer and dryer. I'm glad my stay was only a couple of days. Otherwise, it was a very wonderful experience."
The price is $250
$455 total
includes taxes & fees
Jun 10 - Jun 11
Retreat Near Dover
Family-Friendly Cottage, Walk to the Beach!
Property grounds
Family-Friendly Cottage, Walk to the Beach!
10.0 out of 10, Exceptional, (14)
"Great location "
Family-Friendly Cottage, Walk to the Beach!
First Floor Studio Apartment in Historic Chestertown
Property grounds
First Floor Studio Apartment in Historic Chestertown
9.8 out of 10, Exceptional, (59)
"This was the perfect place to rest our heads along our trip down the east coast. Very comfortable, clean and quiet. We made time to visit the beautiful town and I’m glad we did!"
The price is $110
$164 total
includes taxes & fees
Jun 11 - Jun 12
First Floor Studio Apartment in Historic Chestertown
Entire Townhouse in Rock Hall
Fridge, microwave, oven, stovetop
Entire Townhouse in Rock Hall
10.0 out of 10, Exceptional, (15)
"We have stayed in this neighborhood before on a previous visit, we enjoyed how quiet and friendly the neighborhood is. We will definitely visit again. The house is very, very clean, cozy, and well stocked with all the supplies you could possibly need. We enjoyed sitting out in the evenings and watching the stars!!! Thanks for making our visit complete!!!"
Entire Townhouse in Rock Hall
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
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
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
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.
Rambling Victorian Beach House on Maryland's Eastern Shore
Beach nearby, sun loungers, beach towels
Rambling Victorian Beach House on Maryland's Eastern Shore
10.0 out of 10, Exceptional, (13)
"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
Private pier and pool at this waterfront Chestertown home
Aerial view
Private pier and pool at this waterfront Chestertown home
9.8 out of 10, Exceptional, (22)
"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
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Fridge, microwave, oven, stovetop
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
10.0 out of 10, Exceptional, (3)
"Lark’s Nest was a cute little place! Very clean! The view from the patio was stunning, and if you’re a bird lover you will be in your glory! Bring your binoculars and sit on the deck and wait! House was well equipped with most everything you would need! Host was very quick to write back when asked a question! First time in this area and hopefully be back again in the future!"
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Grasonville Home w/ Private Pool on the Water
Pool
Grasonville Home w/ Private Pool on the Water
10.0 out of 10, Exceptional, (13)
"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
Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |
Property grounds
Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |
10.0 out of 10, Exceptional, (3)
"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 |
BEACH WITHOUT THE BUSTLE
Beach nearby, sun loungers, beach towels
BEACH WITHOUT THE BUSTLE
10.0 out of 10, Exceptional, (21)
"We needed tranquility after returning from a deployment in the Mideast. All was perfect for my team and I."
BEACH WITHOUT THE BUSTLE
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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
Front of property
Bally's Dover Casino Resort
4.0 star property
8.6 out of 10, Excellent, (1373)
"The room was very comfortable, and we enjoyed a restful night's sleep. The bathroom was large and roomy."
The price is $79
$103 total
includes taxes & fees
Jul 1 - Jul 2
Bally's Dover Casino Resort
Red Roof Inn & Suites Dover Downtown
Exterior
Red Roof Inn & Suites Dover Downtown
2.5 star property
7.4 out of 10, Good, (1005)
"It was right on the main highway so restaurants, 7-11 and other stores were all close by."
The price is $84
$92 total
includes taxes & fees
Jun 9 - Jun 10
Red Roof Inn & Suites Dover Downtown
Microtel Inn & Suites by Wyndham Dover
Exterior
Microtel Inn & Suites by Wyndham Dover
2.0 star property
8.0 out of 10, Very Good, (1011)
"Very good experience, a well run hotel. I was very pleased, thank you. "
The price is $89
$98 total
includes taxes & fees
Jun 9 - Jun 10
Microtel Inn & Suites by Wyndham Dover
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.

Everything you need to know about Sudlersville vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Sudlersville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Sudlersville vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Sudlersville vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sudlersville. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Sudlersville in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $110 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Sudlersville rentals

At Expedia, we put the best Sudlersville vacation 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 Sudlersville 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 Sudlersville vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sudlersville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Sudlersville?

Yes, we offer vacation rentals near popular attractions in Sudlersville, or you can go with a secluded option if you'd like a relaxing place to stay. Sudlersville is known for its wineries.

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

Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.: You might want to consider this vacation rental near Sudlersville, which is located on the waterfront and has a private balcony, a private yard, and a barbecue grill 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 you can cook with friends or family. Make the most of the selection 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 larger area.

What are vacation rentals like in Sudlersville?

Vacation rentals are private accommodations you can book for a few days or a quick weekend in Sudlersville. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a clean environment, vacation rentals can provide a sense of security away from public hotel elevators and busy reception areas while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for a small group gathering.

Recent reviews of Sudlersville properties
Expedia verified reviews

Residence Inn Marriott Dover

Residence Inn Marriott Dover

5/5 Excellent
"This property was clean, quiet and the beds was very comfortable "
A verified traveler stayed at Residence Inn Marriott Dover
Posted 15 hours ago
Residence Inn Marriott Dover