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Compare 95 Vacation Homes in Sudlersville with updated reviews, rates, and availability.

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!
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, (23)
"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
Luxurious and spacious townhome with all necessary amenities awaits your stay.
Interior

Luxurious and spacious townhome with all necessary amenities awaits your stay.

10.0 out of 10, Exceptional, (4)
"Great experience all around! "
Luxurious and spacious townhome with all necessary amenities awaits your stay.
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.
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.

9.8 out of 10, Exceptional, (50)
" We ( a group of 16 women) enjoyed having our annual retreat at Nauti or Knot. We stayed for a weekend and the accommodations could not have been better! The bedrooms and bathrooms were wonderful. The living room was able to sit 16 comfortably and the dining room table was big enough for all of us to have dinner together. This is an excellent house!! Our only complaint and it’s minor is that the freezer door was really hard to open."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Waterfront Paradise on the Eastern Shore of Chesapeake Bay
Beach

Waterfront Paradise on the Eastern Shore of Chesapeake Bay

10.0 out of 10, Exceptional, (62)
"Bigger, nicer and newer than it looks in the pics; a pleasant surprise. Great location, we’d go again. "
Waterfront Paradise on the Eastern Shore of Chesapeake Bay
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, (16)
"We had an annual girls trip at this property last weekend and it was perfect and as described! The local food recommendations were on point and the house was clean and well stocked with all we needed. Thank you for opening your home to us!"
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!
Spacious Victorian close to everything in RH - Wheelchair friendly. Sleeps 11
The Elbourne House. Named for the Elbourne family that owned and lived here.

Spacious Victorian close to everything in RH - Wheelchair friendly. Sleeps 11

10.0 out of 10, Exceptional, (11)
"We came for the annual sailboat Race to Rock Hall. We had two sailing teams sharing the house and everyone enjoyed themselves. We’ll be back next year"
Spacious Victorian close to everything in RH - Wheelchair friendly. Sleeps 11
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
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.
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 997 total
includes taxes & fees
30 Dec - 31 Dec
BAYSIDE BUNGALOW
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
Stay in the landmark Lighthouse!
Exterior

Stay in the landmark Lighthouse!

10.0 out of 10, Exceptional, (95)
"We had a combination work/vacation, and the Lighthouse was perfect for both. We highly recommend this unusually designed, spacious, comfortable, and beautifully located house. I saw eagles, herons, and other amazing birds; the sunrise and sunset was lovely (a rainbow at sunrise -- magical!) and the three of us had a great time with lots of room to hang out and have some time apart. Don't hesitate! I will stay here again."
Stay in the landmark Lighthouse!
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!
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
Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully
Pool

Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

10.0 out of 10, Exceptional, (5)
"The house and property were wonderful. Right on the river with all you need. Fantastic stay, great communication, would love to return again!"
Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully
Adorable two-bedroom retreat close to Easton, Denton, Centreville
Outdoor dining

Adorable two-bedroom retreat close to Easton, Denton, Centreville

10.0 out of 10, Exceptional, (16)
"Beautiful property with lots of thoughtful details. "
Adorable two-bedroom retreat close to Easton, Denton, Centreville
River Front, Private Single Family Home
Marina

River Front, Private Single Family Home

10.0 out of 10, Exceptional, (10)
"Beautiful and it was located close to my daughter and her family. It is close to shopping both food and outlets. The morning view of the water was so relaxing and beautiful while having a cup of coffee. There was plenty of room for 4 adults and two kids. I will definitely stay here again. "
River Front, Private Single Family Home
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!
Main Bedroom King - 3rd floor

Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!

10.0 out of 10, Exceptional, (13)
"We booked this home for the Waterman’s Triathlon Weekend. My wife was racing and I like to have a location close to the event so we don’t have to worry about driving/parking/commuting the morning of and this location was EXACTLY what we were looking for! This home was clean, spacious and homey! We had plenty of room for both of us to work remotely for a full day, great lounging living room and the garage access was a great perk as it gave us space to store all of my wife’s triathlon gear for...
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!
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 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, (23)
"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
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.
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.

9.8 out of 10, Exceptional, (50)
" We ( a group of 16 women) enjoyed having our annual retreat at Nauti or Knot. We stayed for a weekend and the accommodations could not have been better! The bedrooms and bathrooms were wonderful. The living room was able to sit 16 comfortably and the dining room table was big enough for all of us to have dinner together. This is an excellent house!! Our only complaint and it’s minor is that the freezer door was really hard to open."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
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.