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Compare 68 Vacation Homes in Cecilton 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
10.0 out of 10, Exceptional, (1)
Pet-Friendly Home on Chester River w/ Dock!
Waterfront house with amazing views. Top of the Chesapeake
December sunrise from the deck

Waterfront house with amazing views. Top of the Chesapeake

10.0 out of 10, Exceptional, (94)
"Cute, up-to-date house, peaceful location, beautiful views. Well supplied kitchen, including sharp knives! Excellent communication with owner – prompt and helpful. Fast internet. Could use more bathroom surface areas; a few more hooks to hang clothes and towels; and an additional umbrella or two outside for shade. My mom, sister, and I thoroughly enjoyed our stay."
Waterfront house with amazing views. Top of the Chesapeake
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
Beach

Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay

9.8 out of 10, Exceptional, (40)
"Very quaint and cute cottage really enjoyed sleeping on the porch , The sound of the waves because it was windy was so soothing. I felt We were on a sailboat."
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Outdoor dining

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

9.8 out of 10, Exceptional, (33)
"The house is cute and clean small house perfect for 9. Comfortable clean linens were provided. Easy to get to. Close to food and easy to get to University of Delaware. Host was easy to get in touch with. The only thing was no TV at all but we enjoyed our time."
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Historic home in the heart of Main Street- walkable to shops and restaurants
Exterior detail

Historic home in the heart of Main Street- walkable to shops and restaurants

10.0 out of 10, Exceptional, (9)
"We really enjoyed the property. The location was within walking distance to the downtown area providing many food and shopping options. We were in MD for a lacrosse tournament which was minutes away from the house. The house was recently renovated, clean and bright. We had more than enough space for our group of 8."
The price is AED 859
AED 1,692 total
includes taxes & fees
2 Dec - 3 Dec
Historic home in the heart of Main Street- walkable to shops and restaurants
Sweet Little Home Away From Home, North East, MD
Outdoor dining

Sweet Little Home Away From Home, North East, MD

10.0 out of 10, Exceptional, (4)
"My family enjoyed our stay at Angela's house in North East. The house was clean, beds were comfortable, kitchen had what we needed. We'd stay there again."
Sweet Little Home Away From Home, North East, MD
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, (35)
"This house had the most amazing views and was clean and tidy. It was perfect for us and the dogs. The yard was clean and mowed and provided plenty of room for frisbee play which is part of my german shepherd's job. The kitchen was very adequate for our needs! As expected, the upstairs bedrooms were "historic" and the staircase was steep also "historic". The showers were perfect. We had a great visit and would love to come back here!"
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Chesapeake City Quiet Overlook
Backyard looking from Ben Cardin trail and the C&D Canal

Chesapeake City Quiet Overlook

10.0 out of 10, Exceptional, (12)
"This home was absolutely magnificent! Location and scenery were wonderful. Just so much to keep our attention and kept us in awe. This was a family trip with siblings and soooo many wonderful memories were made. We are older now and it means more than ever before. Thank you to our host Jane who kept in touch and was so very attentive. Most gracious. We are already talking about going back. Cannot say enough it thank you from the bottom of our hearts.♥️"
Chesapeake City Quiet Overlook
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, (7)
"More than expected. Great locatiom. Everything. But hot chocolate pods provided. Loved it"
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
Spacious North East Home w/ Fenced Yard & Fire Pit
North East Vacation Rental | 5BR | 3BA | 1,990 Sq Ft | Stairs Required

Spacious North East Home w/ Fenced Yard & Fire Pit

10.0 out of 10, Exceptional, (6)
"This was a wonderful home. The amenities were great, the home was clean and the communication couldn't have been better. "
Spacious North East Home w/ Fenced Yard & Fire Pit
Tip Of The Town Fresh and New 3 Bedroom Nest
Exterior

Tip Of The Town Fresh and New 3 Bedroom Nest

9.8 out of 10, Exceptional, (7)
"Loved the convenience to the town of South East and Blue Elk Vineyard. The property was very clean. Having an EV charger was so helpful."
The price is AED 661
AED 1,339 total
includes taxes & fees
1 Dec - 2 Dec
Tip Of The Town Fresh and New 3 Bedroom Nest
Saybrook Hall | Pickleball + Pool + Hot Tub
Saybrook Hall - historical colonial home upgraded to an modern, amenity packed vacation destination!

Saybrook Hall | Pickleball + Pool + Hot Tub

Saybrook Hall | Pickleball + Pool + Hot Tub
Luxurious and spacious townhome with all necessary amenities awaits your stay.
Private kitchen

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

10.0 out of 10, Exceptional, (3)
"Great experience all around! "
Luxurious and spacious townhome with all necessary amenities awaits your stay.
The Riverside Oasis waterfront with hot tub

The Riverside Oasis waterfront with hot tub

10.0 out of 10, Exceptional, (1)
"We had a great weekend! The house was amazingly decorated. All the furnishings were comfy and soft. We loved it. There were plenty of games both indoor and outdoor to keep everyone busy. The views from pretty much every room were stunning. Can’t wait to come back!"
The Riverside Oasis waterfront with hot tub
Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!
Concord Point Lighthouse

Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!

9.6 out of 10, Exceptional, (55)
"Porch is filled with cobwebs. Steps inside need a lot of improvement. Inside was very clean, if dated. However I was pleased with the updated shower, refrigerator, kitchen. No tv made the down time lonely. Netflix did not work, nor did dvd player. For me I needed a much more closer bathroom on the second floor. Getting up 3 times a night to use bathroom & navigating those poorly constructed stairs was scary. I did not want to stay in the single bed right by front door. SUZANNE was very...
Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Pool

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

10.0 out of 10, Exceptional, (61)
"Great!"
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Waterfront Home & Dock, sleeps 8 Max. Eastern shore, Betterton Chestertown MD.
Front of House Facing the Water.

Waterfront Home & Dock, sleeps 8 Max. Eastern shore, Betterton Chestertown MD.

9.8 out of 10, Exceptional, (87)
"The house and location on Still Pond Maryland was great!! House was clean and tiddy. Caught perch, catfish and bass off their dock!! Area is beautiful and quiet! "
Waterfront Home & Dock, sleeps 8 Max. Eastern shore, Betterton Chestertown MD.
5-bedroom vacation home 5 minutes from historic Charlestown
A fall sunset from the deck.

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (135)
"we had a short stay but wished it was longer, the views from the house and peacefulness of the location were incredible"
The price is AED 1,319
AED 2,398 total
includes taxes & fees
2 Dec - 3 Dec
5-bedroom vacation home 5 minutes from historic Charlestown
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
Miscellaneous

Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

10.0 out of 10, Exceptional, (51)
"The house is roomy and was clean and well stocked."
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!
Welcome to Veazey Cove! This gorgeous blue pool and hot tub feature overlooking the lake and spacious backyard is a favorite of both kids and adults alike!

Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!

9.4 out of 10, Exceptional, (32)
"We had a great time in the pool, fishing off dock, paddle boarding, kayaking and swimming. The kids (5 under 8) loved playing in the bAsement."
Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!
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 Cecilton

First Floor Studio Apartment in Historic Chestertown
Back Yard

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (75)
"EasyvPeasy place."
The price is AED 360
AED 579 total
includes taxes & fees
28 Nov - 29 Nov
First Floor Studio Apartment in Historic Chestertown
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Beach

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (44)
"it being off season,very quiet. the people in the surrounding neighborhood were very friendly, we had a great time, ash and christine were awsome host. we will deffinately go back again!"
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Waterfront house with amazing views. Top of the Chesapeake
December sunrise from the deck

Waterfront house with amazing views. Top of the Chesapeake

10.0 out of 10, Exceptional, (94)
"Cute, up-to-date house, peaceful location, beautiful views. Well supplied kitchen, including sharp knives! Excellent communication with owner – prompt and helpful. Fast internet. Could use more bathroom surface areas; a few more hooks to hang clothes and towels; and an additional umbrella or two outside for shade. My mom, sister, and I thoroughly enjoyed our stay."
Waterfront house with amazing views. Top of the Chesapeake
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.