Church Hill Holiday Rentals

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Holiday Rentals in Church Hill

Cass-N-Reel Luxury Houseboat
10.0 out of 10, Exceptional, (42)
"Great location - very convenient to 50 and restaurants - very clean - greatly appreciated the water and potato chips"
United States
dewey b.
Cass-N-Reel Luxury Houseboat
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
10.0 out of 10, Exceptional, (16)
"I loved the welcome basket! This place was extremely clean and had all the amenities that we needed. Much larger in person than even in the pictures. Walkable to town! "
United States
Tracy S.
The price is AU$455
includes taxes & fees
21 Oct - 22 Oct
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
10.0 out of 10, Exceptional, (10)
"Kayaks were a great plus! Ideal spot for a small family with easy access to the the beautiful Chester River. Our grandchildren had a blast, visiting the pigs, chickens, and sheep that were within easy walking distance."
United States
Douglas N.
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Entire Townhouse in Rock Hall
10.0 out of 10, Exceptional, (32)
"House was exactly as advertised. Quite community. Close to shopping, dining and beach! "
United States
Karla M.
Entire Townhouse in Rock Hall
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
10.0 out of 10, Exceptional, (194)
"We had an amazing stay. The owner has literally thought of everything to make your stay the best experience! We had a range of ages in our family and everyone loved it. The beach was amazing."
United States
Jennifer C.
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (57)
"Lovely cottage, well-equipped, immaculately clean. "
United States
Mary
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (51)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is AU$432
includes taxes & fees
31 Oct - 1 Nov
BAYSIDE BUNGALOW
Spacious Victorian close to everything in RH - Wheelchair friendly. Sleeps 11
10.0 out of 10, Exceptional, (19)
"This charming house was perfect for my family to enjoy a few nights in Rock Hall. It had everything we needed and the owners even gave a warm welcome with snacks and local information to help make our stay more enjoyable. "
United States
KEVIN P.
Spacious Victorian close to everything in RH - Wheelchair friendly. Sleeps 11
Waterfront Retreat with Private Dock and Beach
10.0 out of 10, Exceptional, (24)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is AU$484
includes taxes & fees
23 Oct - 24 Oct
Waterfront Retreat with Private Dock and Beach
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (103)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
United States
Mary
The price is AU$248
includes taxes & fees
20 Oct - 21 Oct
First Floor Studio Apartment in Historic Chestertown
RELAX- Eastern Shore Creek Home - 6 Guests
10.0 out of 10, Exceptional, (5)
"Great property that is well kept. It is a short drive to several wonderful restaurants and an outlet shopping center."
United States
J E.
RELAX- Eastern Shore Creek Home - 6 Guests
WATERFRONT right on a BEACH
10.0 out of 10, Exceptional, (51)
"The property and the view provided us with an absolutely wonderful and relaxing getaway. Perfect for two couples and two little dogs to have the most enjoyable time. Home is comfortable and well stocked with necessities. Tracy is great to communicate with and very responsive. We would love to return sometime soon!"
United States
Sally P.
WATERFRONT right on a BEACH
High Tide Haven Suite
The price is AU$312
includes taxes & fees
20 Oct - 21 Oct
High Tide Haven Suite
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
9.8 out of 10, Exceptional, (51)
"This property was perfect for our trip. It was very clean, comfortable and feels like home. Description and photos on the website were accurate. The owners were very attentive and hospitable. This is definite a place I’ll return to."
United States
Lisa
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Serene Waterfront Cottage with dock and gorgeous views.
9.6 out of 10, Exceptional, (38)
"Nice place with everything I could want. Would stay there again!"
United States
Eric H.
Serene Waterfront Cottage with dock and gorgeous views.
Eastern shore beachfront cottage with stunning sunset views!
10.0 out of 10, Exceptional, (3)
"This property is stunning, from the views, to the accommodations and furnishing. Great location, easy access to town and amenities. The host is responsive, and incredibly kind. Highly recommend!!"
United States
Jessica J.
Eastern shore beachfront cottage with stunning sunset views!
Waterfront Home,Private Dock,Bring Boat,Eastern shore, Betterton,Chestertown
9.8 out of 10, Exceptional, (94)
"The properly is in great shape, clean and well provisioned. The flat back yard is perfect for yard games and when the tide is low, there a little private beach! The kids played in the sand and floated around Still Pound Creek all weekend. Loretta was an excellent host!"
United States
Adam H.
Waterfront Home,Private Dock,Bring Boat,Eastern shore, Betterton,Chestertown
Kent Island Waterfront Cottage
8.8 out of 10, Excellent, (11)
"My husband and I and our bunny stayed here the hottest week of the year for 4 nights and we were grateful to have been kept cool with no issues. The A/C in this unit has been well tested. The condo is secluded and private with all types of wildlife present. We saw deer, a black squirrel, a bunny, birds galore, etc. The unit was clean and cool when we checked in. Check-in was super easy as was check out. The pictures of this condo are 100% accurate. The view is so beautiful you won't want to...
United States
Patricia C.
Kent Island Waterfront Cottage
River Front, Private Single Family Home
10.0 out of 10, Exceptional, (21)
"This place was absolutely stunning, and such a great place for my friends and me to stay for a wedding weekend! The location, size, and amenities were wonderful (the hot tub was a hit). The host, Dave, was a clear and prompt communicator and made us feel very welcome. We would definitely stay here again and again!"
United States
Kaley G.
River Front, Private Single Family Home
Circa 1900 Home in the Heart of Historic Downtown Chestertown
10.0 out of 10, Exceptional, (75)
"Great house, will stay again in the future. "
United States
Gary N.
Circa 1900 Home in the Heart of Historic Downtown Chestertown
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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Top Church Hill Hotel Reviews

Find out more about Church Hill

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, 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 favourite 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 depend 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 per night. Entering your travel dates in the search wizard might find you 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?

240' Private Beachfront @Kent Island Love Point - Great for Large Groups: This holiday home rental outside of Church Hill is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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.