Holiday Rentals in Sudlersville

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Holiday 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
BAYSIDE BUNGALOW
Fridge, microwave, coffee/tea maker, toaster
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (19)
"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 €261
per night
19 Jun - 20 Jun
BAYSIDE BUNGALOW
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, (20)
"Thoroughly enjoyed our stay! Betty is such a great host. Beautiful area...GREAT sunsets and close to the beach! Very comfortable weekend stay! Also close to some great wineries and Alpaca farms!"
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.
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.
200 steps to the beach!
Interior
200 steps to the beach!
10.0 out of 10, Exceptional, (77)
"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
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
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Sun-loungers, beach towels
Secluded Waterfront Cottage on 200 acre farm near Queenstown
10.0 out of 10, Exceptional, (90)
"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
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
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, (60)
"It was a nice room in a nice neighborhood. Only complaint would be the coffee maker was awful."
The price is €157
per night
20 Jun - 21 Jun
First Floor Studio Apartment in Historic Chestertown
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.
9.6 out of 10, Exceptional, (4)
"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 |
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."
The price is €2,117
per night
18 Jul - 19 Jul
Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |
Eastern Shore beach cottage get-away
Sun-loungers
Eastern Shore beach cottage get-away
10.0 out of 10, Exceptional, (123)
"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
Fridge, microwave, oven, stovetop
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC
10.0 out of 10, Exceptional, (2)
"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
Beach towels
Peaceful getaway convenient to local amenities including beach, boating & food
9.8 out of 10, Exceptional, (105)
"Second time staying as this property and will continue to be our go to vrbo when needed. Very comfortable and has everything needed while in Rock Hall. Had some difficulty opening up door with key pad initially, but was able to figure it out. Highly recommend this property."
Peaceful getaway convenient to local amenities including beach, boating & food
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.
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.
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
Grasonville Home w/ Private Pool on the Water
Pool
Grasonville Home w/ Private Pool on the Water
10.0 out of 10, Exceptional, (14)
"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
Interior
Home away from home
7.6 out of 10, Good, (5)
"Nice place to stay for quick weekend. Close to everything."
Home away from home
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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, (1395)
"I liked the Price."
The price is €83
per night
1 Jul - 2 Jul
Bally's Dover Casino Resort
Microtel Inn & Suites by Wyndham Dover
Exterior
Microtel Inn & Suites by Wyndham Dover
2.0 star property
8.0 out of 10, Very good, (1000)
"Excellent staff and clean room, wish it had ice machine but everything was great!"
The price is €90
per night
19 Jun - 20 Jun
Microtel Inn & Suites by Wyndham Dover
Red Roof Inn & Suites Dover Downtown
Exterior
Red Roof Inn & Suites Dover Downtown
2.5 star property
7.4 out of 10, Good, (1001)
"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 €83
per night
19 Jun - 20 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.

Everything you need to know about Sudlersville 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 Sudlersville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 Sudlersville holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Sudlersville holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sudlersville 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 Sudlersville holiday rentals we have selected for you start as low as €157 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Sudlersville rentals

At Expedia, we put the best Sudlersville 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 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 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 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 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

Hilton Garden Inn Dover

Hilton Garden Inn Dover

5/5 Excellent
"Convenient"
A verified traveller stayed at Hilton Garden Inn Dover
Posted 2 days ago
Hilton Garden Inn Dover