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
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

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, (23 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 ￥10,722
￥19,722 total
includes taxes & fees
Aug 10 - Aug 11
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
9.6 out of 10, Exceptional, (119 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is ￥15,609
￥25,044 total
includes taxes & fees
Aug 11 - Aug 12
First Floor Studio Apartment in Historic Chestertown
Smart TV, books

3. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (31 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveler
The price is ￥35,476
￥55,522 total
includes taxes & fees
Aug 20 - Aug 21
Newly restored apartment in the heart of Chestertown
Interior

4. Cozy Room in Dover

Cozy Room in Dover
Dover
The price is ￥9,224
￥15,157 total
includes taxes & fees
Aug 11 - Aug 12
Cozy Room in Dover
Property grounds

5. 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 ￥56,704
￥86,336 total
includes taxes & fees
Sep 2 - Sep 3
Wren Retweet- Country Estate in Center of C’Town
Interior

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
9.8 out of 10, Exceptional, (10 reviews)
"The pictures were accurate. Our host communicated with us in a timely manner. Everything was as it said it was going to be everything in the house worked and made sense. We really enjoyed our stay. We definitely will be staying at this location again when we come in into Dover."
United States
Laura
The price is ￥17,344
￥27,585 total
includes taxes & fees
Sep 6 - Sep 7
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
TV, fireplace

7. 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 ￥28,948
￥44,368 total
includes taxes & fees
Aug 19 - Aug 20
Secluded Cottage in Middle of Chestertown
Exterior detail

8. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (61 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is ￥31,534
￥47,799 total
includes taxes & fees
Aug 9 - Aug 10
BAYSIDE BUNGALOW
Beach

9. 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, (28 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is ￥19,551
￥46,468 total
includes taxes & fees
Aug 10 - Aug 11
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
1 bedroom, WiFi, bed sheets

10. Turtle Cove Room

Turtle Cove Room
Kent County
The price is ￥22,137
￥27,471 total
includes taxes & fees
Aug 10 - Aug 11
Turtle Cove Room
Beach nearby

11. Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (26 reviews)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is ￥35,476
￥59,691 total
includes taxes & fees
Aug 30 - Aug 31
Waterfront Retreat with Private Dock and Beach
Property grounds

12. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (15 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is ￥56,761
￥96,100 total
includes taxes & fees
Aug 10 - Aug 11
Turnbridge Manor
Interior

13. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (12 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 ￥53,292
￥67,009 total
includes taxes & fees
Sep 2 - Sep 3
Family Retreat at Lansdowne Manor
Property grounds

14. 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 ￥25,148
￥30,922 total
includes taxes & fees
Aug 10 - Aug 11
Beachcomber Suite
Pool

15. Mini Aruba RV/Glamping Tent

Mini Aruba RV/Glamping Tent
Dover
10.0 out of 10, Exceptional, (6 reviews)
"My husband and I stayed for two nights. The oasis makes you feel like you’re vacationing in the Caribbean. The camper is clean and comfortable for two people. Everything was perfect and cannot wait to return!"
United States
Marleen M.
The price is ￥23,651
￥38,275 total
includes taxes & fees
Sep 6 - Sep 7
Mini Aruba RV/Glamping Tent
Dining

16. 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, (15 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 ￥39,418
￥66,017 total
includes taxes & fees
Aug 10 - Aug 11
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Smart TV

17. Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (4 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is ￥28,393
￥58,354 total
includes taxes & fees
Aug 25 - Aug 26
Bayside Cottage steps from Rock Hall Harbor
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

Comfort Inn & Suites Dover near Speedway

Comfort Inn & Suites Dover near Speedway

10/10 Excellent
"Overall our stay was nice and the staff was very helpful."
tamyra 2-night trip
Posted 16 hours ago
Comfort Inn & Suites Dover near Speedway

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?

Stay in the landmark Lighthouse!: Visitors like this Sudlersville vacation home rental. It offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the 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 Crumpton Auction, or get outside and enjoy nature at Betterton Beach. Rolphs Wharf Marina and Crow Farm and Vineyard 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.