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Sudlersville Vacation Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

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, (26 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.
$118 nightly
The price is $125
Aug 11 - Aug 12
Total with taxes and fees
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.
$144 nightly
The price is $159
Aug 11 - Aug 12
Total with taxes and fees
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
$319 nightly
The price is $352
Aug 20 - Aug 21
Total with taxes and fees
Newly restored apartment in the heart of Chestertown
Interior

4. Cozy Room in Dover

Cozy Room in Dover
Dover
$94 nightly
The price is $96
Aug 15 - Aug 16
Total with taxes and fees
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.
$481 nightly
The price is $500
Sep 2 - Sep 3
Total with taxes and fees
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
$159 nightly
The price is $163
Sep 6 - Sep 7
Total with taxes and fees
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.
$272 nightly
The price is $282
Aug 19 - Aug 20
Total with taxes and fees
Secluded Cottage in Middle of Chestertown
Exterior detail

8. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (62 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
$260 nightly
The price is $276
Aug 11 - Aug 12
Total with taxes and fees
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.
$264 nightly
The price is $291
Aug 12 - Aug 13
Total with taxes and fees
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
$160 nightly
The price is $174
Aug 17 - Aug 18
Total with taxes and fees
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.
$343 nightly
The price is $379
Aug 30 - Aug 31
Total with taxes and fees
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.
$579 nightly
The price is $614
Aug 11 - Aug 12
Total with taxes and fees
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.
$365 nightly
The price is $404
Sep 2 - Sep 3
Total with taxes and fees
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.
$183 nightly
The price is $198
Aug 24 - Aug 25
Total with taxes and fees
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.
$217 nightly
The price is $223
Sep 6 - Sep 7
Total with taxes and fees
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
$400 nightly
The price is $424
Aug 11 - Aug 12
Total with taxes and fees
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.
$360 nightly
The price is $382
Sep 2 - Sep 3
Total with taxes and fees
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.
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Top Sudlersville Hotel Reviews

Bally's Dover Casino Resort

Bally's Dover Casino Resort

8/10 Good
"clean room, nice staff, fun"
Pamela 1-night trip
Posted less than an hour ago
Bally's Dover Casino Resort

Find out more about Sudlersville

Everything you need to know about Sudlersville vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Sudlersville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Sudlersville vacation 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 low season months. For more hustle and bustle, you may prefer to visit Sudlersville in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $159 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Sudlersville rentals

At Expedia, we put the best Sudlersville vacation 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 vacation.

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 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: Visitors like this Sudlersville vacation home rental. It 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 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.