Sudlersville Holiday Rentals

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Holiday Rentals in Sudlersville

Charming 3-bedroom Ranch in delightful Dover with AC

Dover
10.0 out of 10, Exceptional, (1)
"Host was great"
United States
mark o.
Charming 3-bedroom Ranch in delightful Dover with AC

BAYSIDE BUNGALOW

Rock Hall
10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is AU$463
includes taxes & fees
1 Jan - 2 Jan 2026
BAYSIDE BUNGALOW

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Earleville
9.8 out of 10, Exceptional, (59)
"Lovely cottage, well-equipped, immaculately clean. "
United States
Mary
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

200 steps to the beach!

Rock Hall
10.0 out of 10, Exceptional, (93)
"Beautiful, comfortable home in a great location. "
United States
Stephanie C.
200 steps to the beach!

First Floor Studio Apartment in Historic Chestertown

Chestertown
9.6 out of 10, Exceptional, (107)
"Amazing and neat and very private "
United States
Alexander M.
The price is AU$245
includes taxes & fees
8 Dec - 9 Dec
First Floor Studio Apartment in Historic Chestertown

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Rock Hall
9.8 out of 10, Exceptional, (40)
"Ashleigh was amazing as a host, got right back to us on all questions and needs. "
United States
Tim B.
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Private Riverfront Home with Hot Tub, Kayaks, Paddleboards and Riverside Firepit

Grasonville
10.0 out of 10, Exceptional, (24)
"Place was fantastic!"
United States
larry
Private Riverfront Home with Hot Tub, Kayaks, Paddleboards and Riverside Firepit

Stay in the landmark Lighthouse!

Rock Hall
10.0 out of 10, Exceptional, (107)
"Beautiful home. Wish I could of stayed longer "
United States
Pat R.
Stay in the landmark Lighthouse!

Stunning waterfront villa with indoor pool and kids swing set and play area.

Earleville
9.8 out of 10, Exceptional, (19)
"Had a good time, grandkids never came out of the pool"
United States
Michael D.
Stunning waterfront villa with indoor pool and kids swing set and play area.

Chesapeake Bay Harbor View in a central location to events/restaurants

2.5 star property
Rock Hall
10.0 out of 10, Exceptional, (2)
"House was clean, great location. Furniture needs a little updating but overall our stay was great! Would definitely stay here again."
United States
Todd W.
The price is AU$416
includes taxes & fees
12 Dec - 13 Dec
Chesapeake Bay Harbor View in a central location to events/restaurants

Waterfront! Private Dock, Boat Tie-Up & Near Town

Rock Hall
10.0 out of 10, Exceptional, (2)
"A beautiful spot."
United States
Laura S.
Waterfront! Private Dock, Boat Tie-Up & Near Town

Waterfront Paradise on the Eastern Shore of Chesapeake Bay

Rock Hall
10.0 out of 10, Exceptional, (73)
"This trip was a girls get away & we thoroughly enjoyed ourselves .. the house was by far the best I’ve ever rented .. clean, well appointed, & decor was gorgeous … the owner was so attentive & acted on anything we needed right away .. I highly recommend this property & we will definitely be returning …"
United States
Denise O.
Waterfront Paradise on the Eastern Shore of Chesapeake Bay

Waterfront Retreat with Private Dock and Beach

Worton
10.0 out of 10, Exceptional, (25)
"If you’re looking for a relaxing scenic getaway as a couple or a family …this retreat is it! The views from the dock were amazing and it was very peaceful. The kids loved playing on the sandy beach area by the dock! We also explored some beach areas nearby. The place was beautiful and perfect for our family of 4! The hosts were great and very helpful!"
United States
Andrea M.
The price is AU$482
includes taxes & fees
7 Dec - 8 Dec
Waterfront Retreat with Private Dock and Beach

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Rock Hall
10.0 out of 10, Exceptional, (17)
"I loved the welcome basket! This place was extremely clean and had all the amenities that we needed. Much larger in person than even in the pictures. Walkable to town! "
United States
Tracy S.
The price is AU$434
includes taxes & fees
6 Dec - 7 Dec
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Circa 1900 Home in the Heart of Historic Downtown Chestertown

Chestertown
10.0 out of 10, Exceptional, (76)
"Great house, will stay again in the future. "
United States
Gary N.
Circa 1900 Home in the Heart of Historic Downtown Chestertown

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Chestertown
10.0 out of 10, Exceptional, (12)
"Kayaks were a great plus! Ideal spot for a small family with easy access to the the beautiful Chester River. Our grandchildren had a blast, visiting the pigs, chickens, and sheep that were within easy walking distance."
United States
Douglas N.
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Grays Inn Creek Waterfront Pvt. Dock Kayaks & View

Rock Hall
10.0 out of 10, Exceptional, (2)
"Really beautiful property right on the lake. Fantastic dinning space, where everyone gathered for meals."
United States
Emma A.
Grays Inn Creek Waterfront Pvt. Dock Kayaks & View

Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!

Rock Hall
10.0 out of 10, Exceptional, (29)
"I've stayed at many bnbs and this one felt the most luxurious/resort-like! Many comforts and homey touches. Close enough to walk places, far enough for peace and quiet. "
United States
Julie L.
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!

Waterfront Lodge packed with Amenities

Earleville
10.0 out of 10, Exceptional, (3)
"Beautiful home. Gorgeous views of Bohemian River. Well maintained House and fully supplied. Our families and friends just loved it. They were already speaking about wanting to return again. "
United States
Virginia G.
Waterfront Lodge packed with Amenities

Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.

Galena
9.8 out of 10, Exceptional, (24)
"Wonderful property, well stocked, and great location. Would definitely stay here again!"
United States
Ken K.
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
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.
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Top Sudlersville Hotel Reviews

Find out more about Sudlersville

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, 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 favourite 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 depend 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 AU$245 per night. Entering your travel dates in the search wizard might find you 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?

BAYSIDE BUNGALOW: This holiday home rental outside of Sudlersville is equipped with a patio, air conditioning and WiFi to help you feel comfortable during your stay. Kitchen amenities include a fridge, a microwave and a coffee maker.

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.