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Check prices for these dates

Next weekend
31 Jan - 2 Feb
In two weeks
7 Feb - 9 Feb
In one month
21 Feb - 23 Feb
In two months
21 Mar - 23 Mar

Compare 98 Vacation Homes in Sudlersville with updated reviews, rates, and availability.

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Terrace/patio

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

10.0 out of 10, Exceptional, (46)
"We had a wonderful time. The home is absolutely fabulous! We are already talking about when we can return. Peaceful and restorative, just what we needed. "
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Newly remodeled 6 BR, 5.5 BA Waterfront with upper deck and private pier

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

10.0 out of 10, Exceptional, (51)
"We really enjoyed everything, location and house was really great. I think neighbors should be more understanding, that it is a vacation property so some sounds should be expected."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Pet-Friendly Home on Chester River w/ Dock!
Chestertown Vacation Rental | 4BR | 4.5BA | 6 Steps Required | 3,232 Sq Ft

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.0 out of 10, Wonderful, (2)
"no kettle no cutting board"
Pet-Friendly Home on Chester River w/ Dock!
Cozy 5 bedroom house with attached guest suite
Exterior

Cozy 5 bedroom house with attached guest suite

Cozy 5 bedroom house with attached guest suite
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Waterfront with private pier and great views

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

10.0 out of 10, Exceptional, (24)
"Very nice house to stay for the holiday. Perfect layout. Great communication with the owners. View gorgeous. "
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
BAYSIDE BUNGALOW
Exterior detail

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (33)
"The bay cottage's porch was a perfect spot to enjoy a bottle of wine and snacks provided by the thoughtful hosts. Clever decor , furnishings, and sauna made our stay special and warm. Had crab dinner viewing sunset over the bay at dockside suggested by hosts. we hope to return. "
The price is AED 643
AED 981 total
includes taxes & fees
25 Jan - 26 Jan
BAYSIDE BUNGALOW
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!
Exterior

Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!

10.0 out of 10, Exceptional, (18)
"Good location."
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!
RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING
Living area

RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING

7.4 out of 10, Good, (3)
"About a 10 minute walk to main street, 15-20 to the Marinas. The house is cute, has a nice common room, and the bed was comfy."
RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Betterton Beachhouse - historic Buena Vista, overlooking the Chesapeake Bay

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

9.6 out of 10, Exceptional, (36)
"We had a great time at the house with friends from our apartment building and neighborhood for the long Thanksgiving weekend. Debbie and Bob had everything we needed to cook with, the porch overlooking the Bay was amazing, and the living room, TV room and dining room were all used frequently. We also played games, and had a nice fire in the portable fire pit outside. Weather got coooold but the house was always warm and cozy. It was a really fun stay. The bedrooms were great, too. They've taken...
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Waterfront family resort Lodge with private pier, game room and bar
The Twin Ponds Lodge sits on over 7 acres of private waterfront property.

Waterfront family resort Lodge with private pier, game room and bar

9.8 out of 10, Exceptional, (24)
"The property was excellent for a large group. We was there for a Sailing Regatta on the lake in front of the house. The perfect house for groups."
Waterfront family resort Lodge with private pier, game room and bar
Grasonville Home w/ Private Pool on the Water
Grasonville Vacation Rental | 3BR | 2BA | Stairs Required for Access

Grasonville Home w/ Private Pool on the Water

9.8 out of 10, Exceptional, (20)
"We started an annual tradition to rent this house with friends. Love the property, beautiful views and great location. Making great memories that will last a lifetime. Thank you for allowing us to use your beautiful home! :)"
Grasonville Home w/ Private Pool on the Water
200 steps to the beach!
Cottage style house

200 steps to the beach!

10.0 out of 10, Exceptional, (85)
"I enjoyed my stay. I've stayed in the house before."
200 steps to the beach!
Private Yard: Pet-Friendly Home in Dover
Dover Vacation Rental | 3BR | 2.5BA | 2,900 Sq Ft | Stairs Required for Access

Private Yard: Pet-Friendly Home in Dover

10.0 out of 10, Exceptional, (12)
"Quiet location, clean and big. "
Private Yard: Pet-Friendly Home in Dover
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Front Porch

Circa 1900 Home in the Heart of Historic Downtown Chestertown

10.0 out of 10, Exceptional, (65)
"Great space. Cozy fireplace. Well appointed house. Perfect location, we walked everywhere."
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
Master bedroom.. King-size bed and en-suite bathroom.

Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

10.0 out of 10, Exceptional, (8)
"This home had to have been the most perfect VRBO we have stayed in. The home was clean, comfortable, stocked with amenities that made the stay incredibly pleasant and in a fantastic location. We particularly enjoyed the built in speakers in the dining room. I would highly recommend this home for a visit to Chestertown. "
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
Right in the center of everywhere in Dover
Game room

Right in the center of everywhere in Dover

8.0 out of 10, Very Good, (3)
"Everything was nice enough space for everyone to sleep comfortably."
Right in the center of everywhere in Dover
Gorgeous Creek Side Ranch-Style Estate With Dock

Gorgeous Creek Side Ranch-Style Estate With Dock

9.8 out of 10, Exceptional, (6)
"We were in town for a family wedding and throughly enjoyed our stay at this beautiful house. The property is gorgeous and the house has everything you need to make your stay enjoyable. We will definitely be back when visiting family in the area. "
Gorgeous Creek Side Ranch-Style Estate With Dock
Your perfect Maryland escape awaits!
Room

Your perfect Maryland escape awaits!

10.0 out of 10, Exceptional, (4)
"Property was as described and according to photos. Children’s toys only consisted of card games, and there was no children’s dinnerware which was listed as provided. Kitchen was not well stocked, as there were no baking supplies and we needed to use the oven. Beds were comfortable and there was ample bedding, pillows, blankets, and towels. There was ample parking. Ceiling fans were amazingly quiet and appreciated in each room. Was difficult to use showers only for children’s baths. Property...
Your perfect Maryland escape awaits!
Langford Creek Estate | Waterfront w/ HOT TUB + Deck!
Welcome to Langford Creek Estate- a beautiful waterfront estate with an extensive amenity list!

Langford Creek Estate | Waterfront w/ HOT TUB + Deck!

9.2 out of 10, Wonderful, (5)
"The owners were very flexible with us and understanding when it came to a booking mistake on my end. The house is lovely and the property is absolutely gorgeous. The deck was picture perfect. Highly recommend for a getaway on the eastern shore!"
Langford Creek Estate | Waterfront w/ HOT TUB + Deck!
Brand New, Waterfront House on Beautiful Fairlee Creek
Terrace/patio

Brand New, Waterfront House on Beautiful Fairlee Creek

Brand New, Waterfront House on Beautiful Fairlee Creek
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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Other property types in Sudlersville

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Terrace/patio

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

10.0 out of 10, Exceptional, (46)
"We had a wonderful time. The home is absolutely fabulous! We are already talking about when we can return. Peaceful and restorative, just what we needed. "
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Newly remodeled 6 BR, 5.5 BA Waterfront with upper deck and private pier

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

10.0 out of 10, Exceptional, (51)
"We really enjoyed everything, location and house was really great. I think neighbors should be more understanding, that it is a vacation property so some sounds should be expected."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Waterfront with private pier and great views

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

10.0 out of 10, Exceptional, (24)
"Very nice house to stay for the holiday. Perfect layout. Great communication with the owners. View gorgeous. "
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
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.