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Sudlersville Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Sudlersville holiday rentals

A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

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

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.8 out of 10, Exceptional, (30 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
United States
Quinton
The price is AU$172
includes taxes & fees
9 Nov - 10 Nov
Guest Suite for up to 2 in a Victorian on the Chester River
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

2. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (133 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is AU$221
includes taxes & fees
9 Nov - 10 Nov
First Floor Studio Apartment in Historic Chestertown
A garden path leading to a wooden building with a rustic appearance.

3. Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
The price is AU$397
includes taxes & fees
9 Nov - 10 Nov
Secluded Cottage in Middle of Chestertown
A kitchen with a wooden island, built-in cabinets, and a window providing a view of the outdoors.

4. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
8.0 out of 10, Very good, (1 review)
"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...
United States
Miriam G.
The price is AU$403
includes taxes & fees
14 Nov - 15 Nov
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A spacious living area with a dining table, sofa, and a kitchen in the background.

5. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (34 reviews)
"Enjoyable stay. All was as advertised. The host was very helpful when asked for information. Location was wonderful, very central in the old part of town. We had a great time!"
United States
Susan A.
The price is AU$483
includes taxes & fees
9 Nov - 10 Nov
Newly restored apartment in the heart of Chestertown
A room with a wooden bench, a vase with flowers, and a door leading to an outdoor area with trees.

6. Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
Dover
10.0 out of 10, Exceptional, (12 reviews)
"Nice clean place. Highly recommended."
United States
Richard B.
The price is AU$222
includes taxes & fees
29 Nov - 30 Nov
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
A kitchen with wooden cabinets, a dining table, and a refrigerator.

7. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (14 reviews)
"We had an amazing stay for a wedding weekend! Beautiful grounds, beautiful house, lots of room for kids and dogs. Would definitely stay again! "
United States
Emily C.
The price is AU$416
includes taxes & fees
9 Nov - 10 Nov
Family Retreat at Lansdowne Manor
A covered porch with a wooden bench, potted plants, and a decorative railing.

8. Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"Perfect location for exploring the cutest town. "
United States
Mandy D.
The price is AU$657
includes taxes & fees
9 Nov - 10 Nov
Wren Retweet- Country Estate in Center of C’Town
A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

9. Turtle Cove Room

Turtle Cove Room
Kent County
10.0 out of 10, Exceptional, (1 review)
"The host was very communicative. The room was clean. It was quiet and peaceful. There were blackout curtains on the windows. A very pleasant stay."
United States
Jennifer M.
The price is AU$281
includes taxes & fees
9 Nov - 10 Nov
Turtle Cove Room
A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

10. Beachcomber Suite

Beachcomber Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...
United States
Lisa E.
The price is AU$293
includes taxes & fees
9 Nov - 10 Nov
Beachcomber Suite
A house with a blue front door, two windows, and a small porch.

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

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (33 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is AU$410
includes taxes & fees
12 Nov - 13 Nov
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A building with a gabled roof and a circular vent on the roof.

12. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (67 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is AU$431
includes taxes & fees
9 Nov - 10 Nov
BAYSIDE BUNGALOW
A two-story house with a porch, two windows, and a door.

13. Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD

Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD
Denton
10.0 out of 10, Exceptional, (15 reviews)
"The house was perfect, welcoming and comfortable, will be coming back again"
United States
Dallas S.
The price is AU$501
includes taxes & fees
1 Dec - 2 Dec
Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD
A modern kitchen with white cabinets, stainless steel appliances, and a marble island with bar stools.

14. 5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover

5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover
Dover
10.0 out of 10, Exceptional, (5 reviews)
"Host was great"
United States
mark o.
The price is AU$849
includes taxes & fees
20 Nov - 21 Nov
5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover
A modern kitchen with a large island, bar stools, and pendant lighting.

15. Spacious 5 Bedroom w/Pool, Patio and Theater

Spacious 5 Bedroom w/Pool, Patio and Theater
Magnolia
9.2 out of 10, Wonderful, (12 reviews)
"The host was very accommodating and the house was excellent and served our needs perfectly."
United States
John K.
The price is AU$950
includes taxes & fees
9 Nov - 10 Nov
Spacious 5 Bedroom w/Pool, Patio and Theater
A backyard with a small waterfall, rocks, and a pond with lily pads. There are two blue chairs and a black pot near the waterfall.

16. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (18 reviews)
"Beautiful home. Plenty of space inside with great outdoor spaces. Very clean and easy to contact host. Family friendly-would highly recommend!"
United States
Jessica H.
The price is AU$855
includes taxes & fees
9 Nov - 10 Nov
Turnbridge Manor
A modern living room with a flat-screen TV, a brown sofa, a dining table with placemats, wicker chairs, and a kitchen area with a microwave and stove.

17. Bohemia Hideaway. Escape to a 14 acre peaceful retreat.

Bohemia Hideaway. Escape to a 14 acre peaceful retreat.
Middletown
The price is AU$411
includes taxes & fees
15 Nov - 16 Nov
Bohemia Hideaway. Escape to a 14 acre peaceful retreat.
A kitchen with wooden cabinets, a stove, and a dining table with chairs.

18. Family Friendly Cozy 3 Bedroom Duplex

Family Friendly Cozy 3 Bedroom Duplex
Grasonville
The price is AU$434
includes taxes & fees
9 Nov - 10 Nov
Family Friendly Cozy 3 Bedroom Duplex
Restaurant

19. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
8.0 out of 10, Very good, (1 review)
The price is AU$797
includes taxes & fees
16 Nov - 17 Nov
Bohemia Manor Farm
A covered outdoor seating area with a wooden ceiling, two chairs, a table, and a wicker sofa.

20. Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
Betterton
The price is AU$501
includes taxes & fees
30 Nov - 1 Dec
Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
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

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"The front desk staff were so nice, room very clean."
John 1-night trip
Posted 11 hours ago
Comfort Inn & Suites Chestertown

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$221 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?

Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*: This holiday home rental outside of Sudlersville is located on a river, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

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 Saulsbury Road Park. Rolphs Wharf Marina and Historical Society of Kent County Maryland 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.