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Top Holiday Rentals in Church Hill

Beach nearby, sun-loungers
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (36)
"Waterview cottage is comfortable and very clean. The accommodations look new and we had good sleep. The kitchen has most of the necessary equipment for meal preparation. A baking sheet pan is needed. WiFi and Roku TV was excellent. The primary bedroom bed was so tall/high my wife could not get in or out of it. That necessitated sleeping in the 2 twins. Plus, one of the twins was missing the top mini mattress. The view is mostly of the neighborhood street, nearby homes and their roofs and a small...
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Pool | Outdoor pool
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (52)
"Beautiful and huge property. Paddling in the river was great!"
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Fridge, microwave, coffee/tea maker, toaster
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (16)
"We have been coming to Rock Hall for years and have stayed at the cottage the last two times and we have really enjoyed it. We will be back again and we will stay at this cottage again. My husband loves the sauna. Bill and Hannah"
The price is £216
per night
29 May - 30 May
BAYSIDE BUNGALOW
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Private kitchen
Retreat Near Dover
10.0 out of 10, Exceptional, (1)
"This house was the perfect affordable option for a coaching staff taking a team to the DE sport complex. Way more affordable than the hotels in the area and definitely cleaner. Beautiful field view in the back yard that reminded us of home. Will definitely go back!"
The price is £365
per night
3 Jun - 4 Jun
Retreat Near Dover
Sun-loungers
Eastern Shore beach cottage get-away
10.0 out of 10, Exceptional, (122)
"The cozy cottage is perfectly maintained and well equipped. The bay view is as advertised and lovely. The location in Rock Hall is ideal, quiet and convenient to everything. The property manager is responsive and informative. We had a great, relaxing getaway weekend and look forward to returning."
Eastern Shore beach cottage get-away
Fridge, microwave, oven, stovetop
Entire Townhouse in Rock Hall
10.0 out of 10, Exceptional, (15)
"We have stayed in this neighborhood before on a previous visit, we enjoyed how quiet and friendly the neighborhood is. We will definitely visit again. The house is very, very clean, cozy, and well stocked with all the supplies you could possibly need. We enjoyed sitting out in the evenings and watching the stars!!! Thanks for making our visit complete!!!"
Entire Townhouse in Rock Hall
Smart TV
Coastal Kent Narrows Home on Bay
10.0 out of 10, Exceptional, (4)
"Very nice place to stay, right on the bay"
The price is £281
per night
29 May - 30 May
Coastal Kent Narrows Home on Bay
Interior
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
9.8 out of 10, Exceptional, (14)
"We really enjoyed our (much too short) stay at this waterfront gem!! The property was very clean, had all the amenities that we needed for our time away.... the only complaint is that we didn't have enough time to enjoy it all!! : ) thank you so much, we will be back!"
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Property grounds
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
9.8 out of 10, Exceptional, (80)
"House was fine. Odd they did not provide sheets. Was difficult for folks who came from far away. But the house was lovely and we enjoyed our time there!!"
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
Fridge, microwave, oven, stovetop
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
10.0 out of 10, Exceptional, (19)
"Was very warm and cozy home and right on the water with beach you can easily access"
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Exterior
Cass-N-Reel Luxury Houseboat
10.0 out of 10, Exceptional, (11)
"We enjoyed the property and the proximity to bars/restaurants. We enjoyed the view from the back porch and it is a nice place to relax. We would definitely recommend staying and look forward to booking another stay in the future."
The price is £292
per night
5 Jun - 6 Jun
Cass-N-Reel Luxury Houseboat
Beach
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
10.0 out of 10, Exceptional, (110)
"This is a great place to chill out with spectacular water views. The home has lots of wonderful spaces to hang out, read, watch TV, and look at the spectacular view. We also had fabulous canoe and kayak paddles up Cox Creek and adjacent waterways. Thanks Scott and Harry!"
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Property grounds
First Floor Studio Apartment in Historic Chestertown
9.8 out of 10, Exceptional, (59)
"This was the perfect place to rest our heads along our trip down the east coast. Very comfortable, clean and quiet. We made time to visit the beautiful town and I’m glad we did!"
The price is £132
per night
29 May - 30 May
First Floor Studio Apartment in Historic Chestertown
Fridge, microwave, oven, stovetop
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
10.0 out of 10, Exceptional, (3)
"Lark’s Nest was a cute little place! Very clean! The view from the patio was stunning, and if you’re a bird lover you will be in your glory! Bring your binoculars and sit on the deck and wait! House was well equipped with most everything you would need! Host was very quick to write back when asked a question! First time in this area and hopefully be back again in the future!"
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Pool
Grasonville Home w/ Private Pool on the Water
10.0 out of 10, Exceptional, (12)
"We were in town for a family wedding. The house was spotless, well-stocked and centrally located for our trip. We recommend the property and would come again!"
Grasonville Home w/ Private Pool on the Water
Property grounds
Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |
10.0 out of 10, Exceptional, (2)
"Everything was wonderful & we didn't want to leave! What a Gem! Thank you!"
Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |
Fridge, microwave, oven, stovetop
Waterfront home with private pier is A Shore Thing
10.0 out of 10, Exceptional, (15)
"The home and it's location were fantastic. Very clean and well-appointed. We enjoyed the layout and the space, and the view of the water was amazing in the Fall (kaledscope of colors)! Communication with the host was easy and prompt. Highly recommend and we will be back!"
Waterfront home with private pier is A Shore Thing
Exterior
Guest Suite for up to 2 in a Victorian on the Chester River
The price is £101
per night
30 May - 31 May
Guest Suite for up to 2 in a Victorian on the Chester River
Interior
200 steps to the beach!
10.0 out of 10, Exceptional, (74)
"Just what we needed! I did a 3 day get-a-way with my husband and 3 year old. It was perfect. The house was very cute, clean, and had everything we needed. You cannot beat the location!"
200 steps to the beach!
Balcony
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
10.0 out of 10, Exceptional, (28)
"I organized a large (15 person) bachelorette weekend at this property in early April. It is an absolutely gorgeous house and the host had a number of thoughtful touches - like extra firewood for the firepit, coffee supplies, and a bottle of bubbly for our bride! The beds were comfortable (even the twins!), which was lucky because one bedroom on the breakdown was not really usable, so a handful of guests relocated to one of the 'kid rooms.' We found Ashleigh very responsive both before and...
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Don't see what you're looking for?
See all available properties in Church Hill
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.

Other types of properties in Church Hill you may be interested in

Terrace/patio
Hyatt Place Kent Narrows & Marina
3.0 star property
9.4 out of 10, Exceptional, (312)
"The property has great views of the water front, the marina, access to nearby restaurants, and shopping. They also provide transportation to the nearby restaurants via golf cart. Hotel staff is friendly and helpful. They offer breakfast in the morning. The property is well maintained also. I will definitely stay here again."
The price is £162
per night
4 Jun - 5 Jun
Hyatt Place Kent Narrows & Marina
Exterior
Best Western Kent Narrows Inn
2.5 star property
8.0 out of 10, Very good, (1000)
"Unfortunately I fell in an extremely slippery bathtub. The apparently recently recoated tub surface combined with bath products containing argon oil combined to make the surface of the tub like ice. Our stay otherwise was quite pleasant."
The price is £111
per night
3 Jun - 4 Jun
Best Western Kent Narrows Inn
Terrace/patio
Hilton Garden Inn Kent Island
3.0 star property
9.0 out of 10, Wonderful, (773)
"Hotel I had a wonderful stay bay front view was awesome. Hotel staff was very polite and professional. Very convenient location next to the Jetty one if my favorite spots with outside seating. Will stay again and would definitely recommend to everyone. "
The price is £167
per night
4 Jun - 5 Jun
Hilton Garden Inn Kent Island
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.

Everything you need to know about Church Hill holiday rentals

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

Church Hill holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Church Hill. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Church Hill holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Church Hill holiday rentals we have selected for you start as low as £101 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Church Hill rentals

At Expedia, we put the best Church Hill holiday 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 Church Hill 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 Church Hill holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Church Hill. 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 holiday rentals in Church Hill?

Yes, there are holiday rentals close to the most popular sights in Church Hill, or you can select a more secluded option if you're looking for a relaxing stay. Church Hill is known for its wineries.

What are some of the best holiday rentals that Church Hill has to offer?

Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.: This holiday home rental outside of Church Hill is located on the waterfront, and has a private balcony, a private garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

What can I see and do in Church Hill?

Explore the area and cultural attractions such as Church Hill Theatre, or visit one of the family-friendly sights such as Crumpton Auction. Cassinelli Winery and Vineyards and Rolphs Wharf Marina are a couple of places you'll find in the wider area.

What are holiday rentals like in Church Hill?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Church Hill. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have everything you need. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for family trips.

Recent reviews of Church Hill properties
Expedia verified reviews

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

5/5 Excellent
"The property has great views of the water front, the marina, access to nearby restaurants, and shopping. They also provide transportation to the nearby restaurants via golf cart. Hotel staff is friendly and helpful. They offer breakfast in the morning. The property is well maintained also. I will definitely stay here again."
A verified traveller from Newark stayed at Hyatt Place Kent Narrows & Marina
Posted 4 days ago
Hyatt Place Kent Narrows & Marina