Church Hill Holiday Rentals from €146: Search Short-Term Rentals

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Our top choices for Church Hill holiday 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.

includes taxes & fees

12 Oct - 13 Oct

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.

includes taxes & fees

12 Oct - 13 Oct

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

Riley B.

A deck with outdoor furniture, a potted plant, and a house in the background.

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.

includes taxes & fees

19 Oct - 20 Oct

A living room with a fireplace, patterned furniture, a coffee table, and a bookshelf.

5. Secluded Cottage in Middle of Chestertown

Chestertown

Amy D.

includes taxes & fees

9 Nov - 10 Nov

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

6. Family Retreat at Lansdowne Manor

Centreville

Emily C.

includes taxes & fees

12 Oct - 13 Oct

A hallway with wooden flooring, a door on the right, and a window at the end.

7. Wren Retweet- Country Estate in Center of C’Town

Chestertown

Mandy D.

includes taxes & fees

9 Nov - 10 Nov

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

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

Rock Hall

lisa p.

includes taxes & fees

12 Oct - 13 Oct

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

9. BAYSIDE BUNGALOW

Rock Hall

Diane V.

includes taxes & fees

12 Oct - 13 Oct

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

10. 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.

includes taxes & fees

9 Nov - 10 Nov

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

11. Turtle Cove Room

Kent County

includes taxes & fees

9 Nov - 10 Nov

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

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

Dover

Richard B.

includes taxes & fees

20 Oct - 21 Oct

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.

includes taxes & fees

13 Oct - 14 Oct

A house with a covered porch, a grill, and a propane tank in the yard.

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

Betterton

includes taxes & fees

20 Oct - 21 Oct

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Top Church Hill Hotel Reviews

The Inn at Chesapeake Bay Beach Club

10/10 Excellent

"Had an amazing stay here. The room was spotlessly clean from top to bottom. The linens were fresh, the bathroom was pristine, and everything felt completely sanitized. It’s rare to find a property that pays such close attention to detail. Fantastic housekeeping service!"

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

10/10 Excellent

"The house was perfect for a 50th reunion with high school friends. Plenty of room to spread out, the grounds are gorgeous and pet friendly! Our host was quick to respond to any questions. The location is convenient, lots of fun things in the area, winery around the corner! Not far from Annapolis, hope to come again soon."

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

10/10 Excellent

"Property was incredibly clean, comfortable, and exactly as described. The host was absolutely wonderful—very pleasant and incredibly easy to reach. Whenever we sent a text, her response was incredibly fast, which made our stay completely stress-free. We had a great time and would definitely stay here again!""

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, 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 €146 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?

Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*: This holiday home rental outside of Church Hill is located on a river, and has an outdoor pool, a fireplace and a BBQ 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 that you can immerse yourself in your holiday.

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.

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Check prices for these dates

Our top choices for Church Hill holiday 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