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

Dover Home - 2 Mi to Delaware State University!
Dover Vacation Rental | 3BR | 1.5BA | Stairs Required | 1,240 Sq Ft
Dover Home - 2 Mi to Delaware State University!
9.2 out of 10, Wonderful, (5)
"We attended a program at the college "
Dover Home - 2 Mi to Delaware State University!
Charming Waterfront house with expansive views of the Chesapeake Bay and Sunsets
Outdoor dining
Charming Waterfront house with expansive views of the Chesapeake Bay and Sunsets
10.0 out of 10, Exceptional, (1)
"What a wonderful home, spacious just beautiful! But the view of the bay was everyone’s favorite, we spent 98% of the time outside only inside for eating and sleeping. The grandkids didn’t pick up and electronic device the entire time, they played basketball, fished, cornhole, counting boats. The only time a TV was turned on was to watch Big Blue Madness and the Kentucky/Vandy game (we’re from Kentucky). But if you like TV there is one in every room! This home is very well stocked with everything...
Charming Waterfront house with expansive views of the Chesapeake Bay and Sunsets
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
Newly remodeled 6 BR, 5.5 BA Waterfront with upper deck and private pier
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
10.0 out of 10, Exceptional, (48)
"The house was beautiful. The location was perfect. The owner was very responsive. 5 couples stayed in the house and we would all love to return. Thank you for everything!!"
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
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, (19)
"We stayed at this place for a family wedding at the nearby beach club. In addition to be a convenient location, the views from the house and property were stunning. The style inside the house was quite eclectic which gave it wonderful charm. Coming back at night gave us fits trying to find the driveway but that was a small price to pay for such a great house. "
Grasonville Home w/ Private Pool on the Water
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Exterior
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
9.8 out of 10, Exceptional, (8)
"Stayed here for a wedding was perfect for the group of 4 of us. Living room is bigger than it looks in the photos and the house was well kept/ clean. Host was great and responsive as well!"
The price is AED 735
AED 1,332 total
includes taxes & fees
25 Nov - 26 Nov
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
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
Kent Island Luxury Waterfront
Living area
Kent Island Luxury Waterfront
10.0 out of 10, Exceptional, (5)
"Such a beautiful property. . Wonderful experience. Love to come back again. House is way better than we expected. Gorgeous views and had an amazing experience of moonrise abd sunrise"
Kent Island Luxury Waterfront
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 989 total
includes taxes & fees
23 Nov - 24 Nov
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, (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
New! Stylish downtown home w/awesome outdoor area!
Living area
New! Stylish downtown home w/awesome outdoor area!
10.0 out of 10, Exceptional, (21)
"Great stay, clean and spacious. Lovely outdoor seating area. Convenient to the town of Stevensville, shopping and dining options, coffee house and great location for Kent Island and Annapolis. Loved the home and would definitely stay again! "
New! Stylish downtown home w/awesome outdoor area!
Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!
Pool
Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!
9.8 out of 10, Exceptional, (9)
"Our stay was amazing. The house is beautiful. The views and peaceful location were completely used. We had many fun game nights and dinners around the table, the kitchen easily provided many happy meals. The gas grill, the fire pit were easy to use. The kayaks were a lot of fun. Sitting on the dock enjoying the peaceful quiet mornings was rejuvenating. The pool chairs and umbrellas were really nice. A ping pong table in the garage was a ton of fun too. The extra fridge/freezer was handy and the...
Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!
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
Harbor View Haven | Waterfront w/ HOT TUB + Dock!
Welcome to Harbor View Haven- A luxurious getaway home with gorgeous views!
Harbor View Haven | Waterfront w/ HOT TUB + Dock!
10.0 out of 10, Exceptional, (15)
"My family enjoyed this house so much. The place is perfect for a relaxing gateway with so much peace and nature. Will definitely be back!"
Harbor View Haven | Waterfront w/ HOT TUB + Dock!
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!
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, (64)
"We enjoyed everything about the property."
Circa 1900 Home in the Heart of Historic Downtown Chestertown
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, (14)
"Rock Hall is the perfect little bay town and this property captures that same appeal. Spacious home with great outdoor space. Lovely neighborhood for walks and bike rides. Everything in home worked perfectly. We are certain to return. "
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!
River Front, Private Single Family Home
Marina
River Front, Private Single Family Home
10.0 out of 10, Exceptional, (8)
"The property is very well kept an up to date. Views out on the water are gorgeous. Very comfortable stay for my wife and I, along my parents and our parents 7 week old. Will be back. :) "
River Front, Private Single Family Home
Waterfront Millington Vacation Rental w/ Hot Tub!
Millington Vacation Rental | 7BR | 3BA | Stairs Required | 3,200 Sq Ft
Waterfront Millington Vacation Rental w/ Hot Tub!
10.0 out of 10, Exceptional, (1)
"I stayed at the Millington house with 8 friends and we had a great time getting away from the city and enjoying the quiet. The check-in process was seamless. The highlights were the hot tub, fire pit, and a surprise visit from the neighbor's dog, Lucy. We appreciated the details like board games and fire kit (with s'mores materials). Definitely would stay again!"
Waterfront Millington Vacation Rental w/ Hot Tub!
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!
Rock Hall Retreat w/ Balcony Near Park & Marina!
Rock Hall Vacation Rental | 3BR | 2.5BA | 1,564 Sq Ft | Steps Required
Rock Hall Retreat w/ Balcony Near Park & Marina!
2.0 star property
10.0 out of 10, Exceptional, (2)
"Family fishing trip in Rockhall. Great place, super clean and convenient. The location was close to everything we needed. Will definitely stay here again on next trip!"
Rock Hall Retreat w/ Balcony Near Park & Marina!
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 Church Hill

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
27 Nov - 28 Nov
First Floor Studio Apartment in Historic Chestertown
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, (22)
"The pictures dont do this rental house justice. It was very clean and wonderfully decorated. The seperate unit was ideal for my daughter and her family. The "
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
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
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.