Church Hill Vacation Rentals from $150: Search Short-Term Rentals

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Our top choices for Church Hill vacation rentals

A house with a swimming pool, surrounded by a fence, and two red umbrellas.

1. First Floor Studio Apartment in Historic Chestertown

Chestertown

John R.

$136 nightly

Nov 16 - Nov 17

Total with taxes and fees

A spacious living area with a dining table, sofa, and a kitchen in the background.

2. Newly restored apartment in the heart of Chestertown

Chestertown

Susan A.

$304 nightly

Nov 11 - Nov 12

Total with taxes and fees

A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

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

Millington

Quinton

$110 nightly

Nov 11 - Nov 12

Total with taxes and fees

A kitchen with a wooden island, built-in cabinets, and a window providing a view of the outdoors.

4. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Chestertown

"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...

Miriam G.

$254 nightly

Nov 16 - Nov 17

Total with taxes and fees

A kitchen with wooden cabinets, a dining table, and a refrigerator.

5. Family Retreat at Lansdowne Manor

Centreville

Emily C.

$264 nightly

Nov 11 - Nov 12

Total with taxes and fees

A building with a gabled roof and a circular vent on the roof.

6. BAYSIDE BUNGALOW

Rock Hall

Diane V.

$272 nightly

Nov 11 - Nov 12

Total with taxes and fees

A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

7. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Rock Hall

lisa p.

$256 nightly

Nov 12 - Nov 13

Total with taxes and fees

A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

8. Turtle Cove Room

Kent County

Jennifer M.

$176 nightly

Nov 23 - Nov 24

Total with taxes and fees

A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

9. Beachcomber Suite

Kent County

"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...

Lisa E.

$189 nightly

Nov 23 - Nov 24

Total with taxes and fees

A deck with a view of a marina, including boats and docks.

10. Cass-N-Reel Luxury Houseboat

Grasonville

Yamilet

$232 nightly

Nov 12 - Nov 13

Total with taxes and fees

A room with a wooden bench, a vase with flowers, and a door leading to an outdoor area with trees.

11. Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

Dover

Richard B.

$143 nightly

Nov 29 - Nov 30

Total with taxes and fees

A two-story house with a porch, two windows, and a door.

12. Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD

Denton

Dallas S.

$320 nightly

Dec 1 - Dec 2

Total with taxes and fees

A backyard with a small waterfall, rocks, and a pond with lily pads. There are two blue chairs and a black pot near the waterfall.

13. Turnbridge Manor

Denton

Jessica H.

$576 nightly

Dec 1 - Dec 2

Total with taxes and fees

A kitchen with wooden cabinets, a stove, and a dining table with chairs.

14. Family Friendly Cozy 3 Bedroom Duplex

Grasonville

$293 nightly

Nov 24 - Nov 25

Total with taxes and fees

A wooden staircase leading to a beach with a clear view of the sea.

15. Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

Betterton

$317 nightly

Nov 30 - Dec 1

Total with taxes and fees

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Top Church Hill Hotel Reviews

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent

"Staff was very friendly."

Quality Inn Grasonville near Kent Island

10/10 Excellent

"Staff was friendly and helpful, The room was clean and quiet. The breakfast area was clean and coffee and tea available 24 hours a day. Was a very pleasant stay. There is a Denny’s in easy walking distance but no other restaurants were within convenient walking distance."

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

10/10 Excellent

"Betty Ann was amazing to partner with. The space was beautiful, sunsets did not disappoint and we loved being on the water for over 3 weeks! The community members we encountered were so kind and welcoming. Would highly recommend anyone who wants a relaxing, beautiful space to get away! Looking forward to our next stay already"

240' Private Beachfront @Kent Island Love Point - Great for Families

10/10 Excellent

"To have this amount of waterfront property to include two small beach areas with a circular walking path to and from the house is truly unique. The sunrises over the Chester River are beautiful. The view of water from all three levels is stunning. Very tranquil. The firepit with an abundance of firewood was enjoyed by all. The house has lots of character, and was well stocked with everything you need for an enjoyable stay. Communication with Hal was great from start to finish. Would highly recommend to others."

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 $150 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.

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?

Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*: This vacation home near Church Hill is located on a river and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

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.

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Check prices for these dates

Our top choices for Church Hill vacation rentals

1. First Floor Studio Apartment in Historic Chestertown

2. Newly restored apartment in the heart of Chestertown

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

4. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

5. Family Retreat at Lansdowne Manor

6. BAYSIDE BUNGALOW

7. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

8. Turtle Cove Room

9. Beachcomber Suite

10. Cass-N-Reel Luxury Houseboat

11. Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

12. Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD

13. Turnbridge Manor

14. Family Friendly Cozy 3 Bedroom Duplex

15. Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

Find vacation rentals that suit your style

Top Church Hill Hotel Reviews

Holiday Inn Express Annapolis East-Kent Island by IHG

Hilton Garden Inn Kent Island Marina

The Inn at Chesapeake Bay Beach Club

Quality Inn Grasonville near Kent Island

The Lodge at Great Oak Landing

Comfort Inn & Suites Chestertown

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

Kent Island Resort

240' Private Beachfront @Kent Island Love Point - Great for Families

Find out more about Church Hill

Frequently asked questions

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