Church Hill Vacation Rentals from AED 583: Search Short-Term Rentals

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Our top choices for Church Hill vacation rentals

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

1. Newly restored apartment in the heart of Chestertown

Chestertown

Anonymous traveler

AED 1,297 total

includes taxes & fees

5 Oct - 6 Oct

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

2. First Floor Studio Apartment in Historic Chestertown

Chestertown

"This property is delightful. It's very "beachy" and relaxing. There are lots of thoughtful amenities which made our stay smooth. The only thing I would mention is that the property is reached by a set of six stair steps, even though strictly speaking it is on the first floor of the house. That wasn't a problem for us. Other than that, we can highly recommend it. We thoroughly enjoyed our stay here. (My husband wants me to mention that he loved the bed and slept very well.)"

Charr

AED 583 total

includes taxes & fees

1 Oct - 2 Oct

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

3. Secluded Cottage in Middle of Chestertown

Chestertown

Amy D.

AED 1,006 total

includes taxes & fees

30 Sep - 1 Oct

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

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

Chestertown

Mandy D.

AED 1,768 total

includes taxes & fees

6 Oct - 7 Oct

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

5. 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.

AED 1,129 total

includes taxes & fees

6 Oct - 7 Oct

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

6. Family Retreat at Lansdowne Manor

Centreville

Emily C.

AED 1,015 total

includes taxes & fees

30 Sep - 1 Oct

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

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

Millington

Riley B.

AED 459 total

includes taxes & fees

30 Sep - 1 Oct

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

8. BAYSIDE BUNGALOW

Rock Hall

Diane V.

AED 1,159 total

includes taxes & fees

30 Sep - 1 Oct

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

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

Rock Hall

lisa p.

AED 1,079 total

includes taxes & fees

4 Oct - 5 Oct

A spacious living room with a leather sofa, a wooden coffee table, and a fireplace.

10. Bayside Cottage steps from Rock Hall Harbor

Rock Hall

Adam S.

AED 1,335 total

includes taxes & fees

30 Sep - 1 Oct

A dining area with a wooden table and chairs, beige curtains, and a ceiling light fixture.

11. Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Grasonville

Robin

AED 1,865 total

includes taxes & fees

30 Sep - 1 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.

12. Turnbridge Manor

Denton

Glenn S.

AED 2,114 total

includes taxes & fees

30 Sep - 1 Oct

A modern exterior with a black door, a metal staircase, and a lantern.

13. Cass-Away Luxury Houseboat

Grasonville

Jamie L.

A sandy beach with a wooden walkway leading to a calm lake, surrounded by dense green foliage.

14. Waterfront Retreat with Private Dock and Beach

Worton

Max G.

AED 1,101 total

includes taxes & fees

4 Oct - 5 Oct

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

15. 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.

AED 916 total

includes taxes & fees

1 Oct - 2 Oct

A modern kitchen with dark cabinets, a white countertop, and a large window.

16. Cass-N-Reel Luxury Houseboat

Grasonville

Danny B.

AED 954 total

includes taxes & fees

8 Oct - 9 Oct

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

17. Turtle Cove Room

Kent County

AED 838 total

includes taxes & fees

30 Sep - 1 Oct

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

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

Dover

Richard B.

AED 681 total

includes taxes & fees

6 Oct - 7 Oct

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Top Church Hill Hotel Reviews

Hyatt Place Kent Narrows & Marina

10/10 Excellent

"Best spot at Kent Narrows."

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

10/10 Excellent

"This is an excellent setting for my wife's 70th birthday, with three children, their spouses/significant others, and four dogs. The owner was congenial and extremely easy to work with and communicate with. The owner does not understate when saying that the house is well-furnished with what one would need for an extended stay, including spices, cooking oil, storage options, etc. The rooms are comfortable and spacious. The porches have beautiful and expansive views of the water, and the beach was so relaxing. the one issue that we had was with the locking mechanism to get in. We are older and our short-term memory is limited. There was a resulting bit of a dance to enter the code in a timely fashion into the lock to open it. It was helpful to have younger people who are digitally quicker. Otherwise, an excellent stay and we look forward to the next time we can stay."

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!""

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

10/10 Excellent

"We had a wonderful long weekend at the cottage. It is beautifully decorated and very clean. It was perfect for our needs. We spent our days boating on the upper bay (gorgeous weather) and evenings relaxing on the deck with a perfect view of the sunset and turkey point lighthouse. Thank you Chris and we would love to come back next season."

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. Newly restored apartment in the heart of Chestertown

2. First Floor Studio Apartment in Historic Chestertown

3. Secluded Cottage in Middle of Chestertown

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

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

6. Family Retreat at Lansdowne Manor

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

8. BAYSIDE BUNGALOW

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

10. Bayside Cottage steps from Rock Hall Harbor

11. Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

12. Turnbridge Manor

13. Cass-Away Luxury Houseboat

14. Waterfront Retreat with Private Dock and Beach

15. Beachcomber Suite

16. Cass-N-Reel Luxury Houseboat

17. Turtle Cove Room

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

Find vacation rentals that suit your style

Top Church Hill Hotel Reviews

Hyatt Place Kent Narrows & Marina

The Inn at Chesapeake Bay Beach Club

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

The Lodge at Great Oak Landing

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

Holiday Inn Express Annapolis East-Kent Island by IHG

Red Roof Inn & Suites Chestertown

Kent Island Resort

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Frequently asked questions

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