Default HTG hotel image

Sudlersville Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Sudlersville vacation rentals

Exterior

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 ￥10,668
￥17,793 total
includes taxes & fees
Sep 22 - Sep 23
Guest Suite for up to 2 in a Victorian on the Chester River
Property grounds

2. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (125 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is ￥15,531
￥24,919 total
includes taxes & fees
Sep 29 - Sep 30
First Floor Studio Apartment in Historic Chestertown
Interior

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 ￥14,119
￥24,167 total
includes taxes & fees
Sep 30 - Oct 1
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
TV, fireplace

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 ￥28,803
￥42,982 total
includes taxes & fees
Sep 23 - Sep 24
Secluded Cottage in Middle of Chestertown
Smart TV

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

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
The price is ￥34,514
￥49,057 total
includes taxes & fees
Oct 5 - Oct 6
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Beach

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 ￥18,480
￥44,823 total
includes taxes & fees
Sep 22 - Sep 23
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Property grounds

7. 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 ￥47,779
￥75,501 total
includes taxes & fees
Sep 29 - Sep 30
Wren Retweet- Country Estate in Center of C’Town
Pool

8. 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 ￥25,101
￥40,036 total
includes taxes & fees
Sep 28 - Sep 29
Mini Aruba RV/Glamping Tent
Property grounds

9. 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 ￥25,022
￥29,769 total
includes taxes & fees
Sep 28 - Sep 29
Beachcomber Suite
Beach nearby

10. Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (26 reviews)
"Everything was lovely! The dock was beautiful and the accommodations were comfortable.Thanks!"
United States
Max G.
The price is ￥27,454
￥47,359 total
includes taxes & fees
Oct 4 - Oct 5
Waterfront Retreat with Private Dock and Beach
1 bedroom, WiFi, bed sheets

11. Turtle Cove Room

Turtle Cove Room
Kent County
The price is ￥25,415
￥30,197 total
includes taxes & fees
Sep 28 - Sep 29
Turtle Cove Room
Dining

12. 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 ￥60,713
￥73,378 total
includes taxes & fees
Sep 23 - Sep 24
Family Retreat at Lansdowne Manor
Exterior detail

13. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (65 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is ￥31,376
￥49,521 total
includes taxes & fees
Sep 24 - Sep 25
BAYSIDE BUNGALOW
Microwave, oven, stovetop, dishwasher

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, (4 reviews)
"Host was great"
United States
mark o.
The price is ￥37,494
￥85,775 total
includes taxes & fees
Sep 22 - Sep 23
5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover
Smart TV

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 ￥33,415
￥64,189 total
includes taxes & fees
Sep 22 - Sep 23
Bayside Cottage steps from Rock Hall Harbor
Property grounds

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

Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
Galena
9.8 out of 10, Exceptional, (27 reviews)
"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.
Dining

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 ￥43,142
￥79,654 total
includes taxes & fees
Sep 22 - Sep 23
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Property grounds

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 ￥56,477
￥95,619 total
includes taxes & fees
Sep 22 - Sep 23
Turnbridge Manor
Coffee/tea maker, fridge, microwave, oven

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.
Spacious 5 Bedroom w/Pool, Patio and Theater
Luxury House, Multiple Bedrooms, Lake View | Laptop workspace, WiFi (free)

20. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
The price is ￥54,773
￥58,059 total
includes taxes & fees
Oct 4 - Oct 5
Bohemia Manor Farm
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Sudlersville Hotel Reviews

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

8/10 Good
"Unique location with a beachy feel. Comfortable with basic amenities. Communication with the lodge staff was very good as I checked in late and they sent me my room entry information. I would stay there again."
Jane 1-night trip
Posted 6 hours ago
The Lodge at Great Oak Landing

Find out more about Sudlersville

Search for holiday rentals in Sudlersville on Expedia! You can easily find your home rentals, villas, holiday apartments in Sudlersville using one of the methods below:

  • View our selection of featured holiday rentals in Sudlersville
  • Use the map to find apartments and other holiday homes in the Sudlersville neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Sudlersville while they last

Look no further and take a look at our great range of rental properties in Sudlersville!

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?

Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining: You might want to consider this vacation home rental near Sudlersville, which is located near the beach and has a patio, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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. 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.