Church Hill Vacation Rentals

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Dec 9 - Dec 10
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Dec 12 - Dec 14
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Dec 19 - Dec 21

Our top choices for Church Hill vacation rentals

Exterior
Guest Suite for up to 2 in a Victorian on the Chester River

Apartment in Millington

9.6 out of 10, Exceptional, (19)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
$118 nightly
The price is $125
Dec 10 - Dec 11
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
Property grounds
First Floor Studio Apartment in Historic Chestertown

Apartment in Chestertown

9.6 out of 10, Exceptional, (108)
"Amazing and neat and very private "
United States
Alexander M.
$144 nightly
The price is $159
Dec 10 - Dec 11
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Outdoor dining
Chesapeake Bay Harbor View in a central location to events/restaurants

Vacation Home in Rock Hall

2.5 star property
10.0 out of 10, Exceptional, (2)
"House was clean, great location. Furniture needs a little updating but overall our stay was great! Would definitely stay here again."
United States
Todd W.
$257 nightly
The price is $272
Dec 10 - Dec 11
Total with taxes and fees
Chesapeake Bay Harbor View in a central location to events/restaurants
Outdoor dining
BAYSIDE BUNGALOW

Vacation Home in Rock Hall

10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
$260 nightly
The price is $276
Dec 17 - Dec 18
Total with taxes and fees
BAYSIDE BUNGALOW
Property grounds
Turnbridge Manor

Vacation Home in Denton

9.8 out of 10, Exceptional, (12)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
$613 nightly
The price is $650
Dec 29 - Dec 30
Total with taxes and fees
Turnbridge Manor
Beach
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Apartment in Rock Hall

10.0 out of 10, Exceptional, (17)
"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.
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Beach
Waterfront Retreat with Private Dock and Beach

Apartment in Worton

10.0 out of 10, Exceptional, (25)
"If you’re looking for a relaxing scenic getaway as a couple or a family …this retreat is it! The views from the dock were amazing and it was very peaceful. The kids loved playing on the sandy beach area by the dock! We also explored some beach areas nearby. The place was beautiful and perfect for our family of 4! The hosts were great and very helpful!"
United States
Andrea M.
$282 nightly
The price is $311
Dec 10 - Dec 11
Total with taxes and fees
Waterfront Retreat with Private Dock and Beach
Exterior
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Vacation Home in Grasonville

9.6 out of 10, Exceptional, (12)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
$395 nightly
The price is $419
Dec 10 - Dec 11
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Terrace/patio
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Vacation Home in Centreville

10.0 out of 10, Exceptional, (8)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
United States
Renee P.
$420 nightly
The price is $445
Dec 15 - Dec 16
Total with taxes and fees
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Terrace/patio
High Tide Haven Suite

Vacation Home in Kent County

$195 nightly
The price is $202
Dec 10 - Dec 11
Total with taxes and fees
High Tide Haven Suite
Property grounds
New! Stylish downtown home w/awesome outdoor area!

Vacation Home in Stevensville

9.8 out of 10, Exceptional, (26)
"The house was spacious, clean, and in a great location. The owners were available, and easy to communicate with."
United States
Marjorie N.
$502 nightly
The price is $532
Dec 25 - Dec 26
Total with taxes and fees
New! Stylish downtown home w/awesome outdoor area!
Terrace/patio
Grandma’s Cottage will wrap around you like a warm hug

Cottage in Betterton

$393 nightly
The price is $417
Jan 1 - Jan 2, 2026
Total with taxes and fees
Grandma’s Cottage will wrap around you like a warm hug
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

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

10/10 Excellent
"We stayed overnight, coming to meet some people for a business meeting. Monica at the front desk provided great customer service and was extremely helpful in accommodating us. "
Anthony 1-night trip
Posted 2 days ago
Hilton Garden Inn Kent Island Marina

Find out more about Church Hill

Everything you need to know about Church Hill vacation rentals

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

Church Hill vacation 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 low season months. For more hustle and bustle, you may prefer to visit Church Hill in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $159 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Church Hill rentals

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

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Church Hill?

Yes, we give you a choice of vacation rentals near the most popular sights in Church Hill, or you can choose a more remote option if you want a relaxing place to stay. Church Hill is known for its wineries.

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

240' Private Beachfront @Kent Island Love Point - Great for Large Groups: This vacation home near Church Hill is located on the beach and has a fireplace, a patio, and a barbecue grill 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 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 a family-friendly sight such as Crumpton Auction. Cassinelli Winery and Vineyards and Rolphs Wharf Marina are a couple of places you'll find in the larger area.

What are vacation rentals like in Church Hill?

Vacation rentals are private accommodations you can book for a couple days or more in Church Hill. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a vacation rental can offer a sense of privacy away from public hotel elevators and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for small groups.