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Sudlersville Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Sudlersville vacation 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, (28 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
The price is AED 250
AED 459 total
includes taxes & fees
30 Sep - 1 Oct
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, (126 reviews)
"This property is delightful. It's very "beachy" and relaxing. There are lots of thoughtful amenities which made our stay smooth. The only thing I would mention is that the property is reached by a set of six stair steps, even though strictly speaking it is on the first floor of the house. That wasn't a problem for us. Other than that, we can highly recommend it. We thoroughly enjoyed our stay here. (My husband wants me to mention that he loved the bed and slept very well.)"
United States
Charr
The price is AED 364
AED 583 total
includes taxes & fees
1 Oct - 2 Oct
First Floor Studio Apartment in Historic Chestertown
A room with a wooden bench, a vase with flowers, and a door leading to an outdoor area with trees.

3. 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
9.8 out of 10, Exceptional, (10 reviews)
"Nice clean place. Highly recommended."
United States
Richard B.
The price is AED 441
AED 681 total
includes taxes & fees
6 Oct - 7 Oct
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
A living room with a fireplace, patterned furniture, a coffee table, and a bookshelf.

4. 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 AED 674
AED 1,006 total
includes taxes & fees
30 Sep - 1 Oct
Secluded Cottage in Middle of Chestertown
A deck with outdoor furniture, a potted plant, and a house in the background.

5. 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 AED 808
AED 1,129 total
includes taxes & fees
6 Oct - 7 Oct
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

6. 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, (30 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is AED 455
AED 1,032 total
includes taxes & fees
4 Oct - 5 Oct
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
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, (13 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 AED 844
AED 1,015 total
includes taxes & fees
30 Sep - 1 Oct
Family Retreat at Lansdowne Manor
A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

8. 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 AED 747
AED 916 total
includes taxes & fees
1 Oct - 2 Oct
Beachcomber Suite
A hallway with wooden flooring, a door on the right, and a window at the end.

9. 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 AED 1,119
AED 1,674 total
includes taxes & fees
30 Sep - 1 Oct
Wren Retweet- Country Estate in Center of C’Town
A swimming pool with a tiled edge, surrounded by potted plants and outdoor furniture.

10. Mini Aruba RV/Glamping Tent

Mini Aruba RV/Glamping Tent
Dover
10.0 out of 10, Exceptional, (6 reviews)
"My son and I had a great stay here for the weekend, camper was clean and had everything we needed and the family was happy to join us or let us have our privacy. All you could ask for and the backyard pool area is as good as it looks in the pictures. Would go back anytime we are in the area."
United States
Robert N.
The price is AED 588
AED 937 total
includes taxes & fees
12 Oct - 13 Oct
Mini Aruba RV/Glamping Tent
A sandy beach with a wooden walkway leading to a calm lake, surrounded by dense green foliage.

11. Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
9.8 out of 10, Exceptional, (27 reviews)
"Everything was lovely! The dock was beautiful and the accommodations were comfortable.Thanks!"
United States
Max G.
The price is AED 643
AED 1,101 total
includes taxes & fees
4 Oct - 5 Oct
Waterfront Retreat with Private Dock and Beach
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, (66 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is AED 735
AED 1,101 total
includes taxes & fees
30 Sep - 1 Oct
BAYSIDE BUNGALOW
A bunk bed room with white bedding and blue throw blankets.

13. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
The price is AED 1,202
AED 1,274 total
includes taxes & fees
20 Oct - 21 Oct
Bohemia Manor Farm
A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

14. Turtle Cove Room

Turtle Cove Room
Kent County
The price is AED 683
AED 838 total
includes taxes & fees
30 Sep - 1 Oct
Turtle Cove Room
A spacious living room with a leather sofa, a wooden coffee table, and a fireplace.

15. Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (5 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is AED 643
AED 1,265 total
includes taxes & fees
30 Sep - 1 Oct
Bayside Cottage steps from Rock Hall Harbor
A modern kitchen with white cabinets, stainless steel appliances, and a marble island with bar stools.

16. 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, (4 reviews)
"Host was great"
United States
mark o.
The price is AED 878
AED 1,994 total
includes taxes & fees
30 Sep - 1 Oct
5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover
A dining area with a wooden table and chairs, beige curtains, and a ceiling light fixture.

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

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (16 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
The price is AED 1,102
AED 1,865 total
includes taxes & fees
30 Sep - 1 Oct
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
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.

18. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (18 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is AED 1,322
AED 2,114 total
includes taxes & fees
30 Sep - 1 Oct
Turnbridge Manor
A modern kitchen with a large island, bar stools, and pendant lighting.

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

Spacious 5 Bedroom w/Pool, Patio and Theater
Magnolia
9.4 out of 10, Exceptional, (11 reviews)
"The host was very accommodating and the house was excellent and served our needs perfectly."
United States
John K.
The price is AED 953
AED 2,337 total
includes taxes & fees
30 Sep - 1 Oct
Spacious 5 Bedroom w/Pool, Patio and Theater
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

Bally's Dover Casino Resort

Bally's Dover Casino Resort

10/10 Excellent
"I only interacted with front desk staff at check-in and check out they were very pleasant. The hotel itself was just ok. Lobby was beautiful, but the rooms are dated. Just ok for a night."
Frances 1-night trip
Posted 3 hours ago
Bally's Dover Casino Resort

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?

Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*: You might want to consider this vacation home rental near Sudlersville, which is located on a river and has an outdoor pool, a fireplace, and a barbecue grill 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 you can immerse yourself in your vacation.

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 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.