Sudlersville Holiday Rentals

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Holiday Rentals in Sudlersville

Guest Suite for up to 2 in a Victorian on the Chester River

Millington
9.6 out of 10, Exceptional, (19)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is NZ$223
includes taxes & fees
24 Nov - 25 Nov
Guest Suite for up to 2 in a Victorian on the Chester River

First Floor Studio Apartment in Historic Chestertown

Chestertown
9.6 out of 10, Exceptional, (106)
"Amazing and neat and very private "
United States
Alexander M.
The price is NZ$283
includes taxes & fees
25 Nov - 26 Nov
First Floor Studio Apartment in Historic Chestertown

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 NZ$491
includes taxes & fees
23 Nov - 24 Nov
BAYSIDE BUNGALOW

JVA LUXURY HOUSING

Smyrna
10.0 out of 10, Exceptional, (1)
"The house was clean and wonderful. I highly recommend!"
United States
Daryl C.
The price is NZ$1,049
includes taxes & fees
29 Nov - 30 Nov
JVA LUXURY HOUSING

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 NZ$507
includes taxes & fees
24 Nov - 25 Nov
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

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 NZ$485
includes taxes & fees
23 Nov - 24 Nov
Chesapeake Bay Harbor View in a central location to events/restaurants

Amazing Modern house with a full kitchen and parking

Smyrna
9.8 out of 10, Exceptional, (8)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
United States
Laurie S.
The price is NZ$636
includes taxes & fees
23 Nov - 24 Nov
Amazing Modern house with a full kitchen and parking

Spacious 5 Bedroom w/Pool, Patio and Theater

Magnolia
9.8 out of 10, Exceptional, (7)
"Great house for a large family "
United States
Stephanie
The price is NZ$1,175
includes taxes & fees
23 Nov - 24 Nov
Spacious 5 Bedroom w/Pool, Patio and Theater

Turnbridge Manor

Denton
9.8 out of 10, Exceptional, (12)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is NZ$1,073
includes taxes & fees
1 Dec - 2 Dec
Turnbridge Manor

Sparkling new! A Craftsman-style cottage in the heart of Rock Hall

Rock Hall
10.0 out of 10, Exceptional, (2)
"I spent a wonderful 8 nights at the Dragonfly Cottage in the quaint bayside town of Rock Hall. The cottage was in a prime location and perfectly situated for long morning walks around the town. The cottage itself is brand new with every accommodation you can think of to have a comfortable stay. The 3 large bedrooms and open floor plan kitchen / living area provide plenty of space to spread out. Everything was sparkling clean and you can tell the hosts have taken a lot of care to anticipate your...
United States
Alison F.
Sparkling new! A Craftsman-style cottage in the heart of Rock Hall

Heated Pool • Private Backyard • Home Theater

2.0 star property
Middletown
The price is NZ$767
includes taxes & fees
24 Nov - 25 Nov
Heated Pool • Private Backyard • Home Theater

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Grasonville
9.6 out of 10, Exceptional, (12)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is NZ$746
includes taxes & fees
24 Nov - 25 Nov
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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 NZ$555
includes taxes & fees
23 Nov - 24 Nov
Waterfront Retreat with Private Dock and Beach

Chesapeake Bay Retreat W/Breathtaking Views

Rock Hall
10.0 out of 10, Exceptional, (1)
"Beautiful home situated right on the water with everything we could need. Would not hesitate to return! "
United States
josh b.
The price is NZ$1,428
includes taxes & fees
1 Dec - 2 Dec
Chesapeake Bay Retreat W/Breathtaking Views

HGTV quality, private guest suite, country getaway with hot tub & fire pit

Centreville
10.0 out of 10, Exceptional, (8)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
United States
Renee P.
The price is NZ$793
includes taxes & fees
1 Dec - 2 Dec
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Grandma’s Cottage will wrap around you like a warm hug

Betterton
The price is NZ$746
includes taxes & fees
1 Dec - 2 Dec
Grandma’s Cottage will wrap around you like a warm hug

High Tide Haven Suite

Kent County
The price is NZ$356
includes taxes & fees
23 Nov - 24 Nov
High Tide Haven Suite
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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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 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 NZ$283 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?

Chesapeake Bay Harbor View in a central location to events/restaurants: This holiday home rental outside of Sudlersville is located in a rural location, and has an outdoor pool, a patio and a BBQ to put you at ease in your new surroundings. It has 3 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 garden 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 Hazel Miner Monument, or get outside and enjoy nature at Betterton Beach. Tilmon's Island Winery and Cassinelli Winery and Vineyards 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.