Church Hill Vacation Rentals from AED 552: 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.

AED 552 total

includes taxes & fees

16 Nov - 17 Nov

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.

AED 1,231 total

includes taxes & fees

15 Nov - 16 Nov

A person sitting on a wooden deck by a calm body of water, surrounded by greenery.

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

Millington

Quinton

AED 428 total

includes taxes & fees

18 Nov - 19 Nov

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.

AED 1,016 total

includes taxes & fees

20 Nov - 21 Nov

An outdoor patio with a brick wall, a grill, and metal chairs.

5. Family Retreat at Lansdowne Manor

Centreville

Emily C.

AED 1,073 total

includes taxes & fees

15 Nov - 16 Nov

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

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

Rock Hall

lisa p.

AED 1,072 total

includes taxes & fees

21 Nov - 22 Nov

A house with a front porch, a pathway leading to the entrance, and a bicycle parked outside.

7. BAYSIDE BUNGALOW

Rock Hall

Diane V.

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

8. Cass-N-Reel Luxury Houseboat

Grasonville

Yamilet

AED 943 total

includes taxes & fees

15 Nov - 16 Nov

An aerial view of a property with a large house surrounded by lush greenery, a driveway, and a road nearby.

9. Turtle Cove Room

Kent County

Jennifer M.

AED 703 total

includes taxes & fees

23 Nov - 24 Nov

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.

AED 755 total

includes taxes & fees

23 Nov - 24 Nov

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

11. Family Friendly Cozy 3 Bedroom Duplex

Grasonville

AED 1,145 total

includes taxes & fees

24 Nov - 25 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.

AED 556 total

includes taxes & fees

29 Nov - 30 Nov

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

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

Denton

Dallas S.

AED 1,281 total

includes taxes & fees

1 Dec - 2 Dec

A two-story house with a gabled roof, a front porch, and a flag.

14. Turnbridge Manor

Denton

Jessica H.

AED 2,305 total

includes taxes & fees

1 Dec - 2 Dec

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

AED 1,263 total

includes taxes & fees

30 Nov - 1 Dec

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Top Church Hill Hotel Reviews

Holiday Inn Express Annapolis East-Kent Island by IHG

8/10 Good

"Helpful staff, nice location on the river"

Hyatt Place Kent Narrows & Marina

10/10 Excellent

"We stayed in a room with two queens and a balcony facing the water. Gorgeous view. Room was exceptionally clean, spacious and had everything we needed. Staff was very friendly when we arrived at check in, personable and informative. The breakfast buffet was massive, had many options. Next door to the hotel, was a delicious restaurant, the Fisherman's Inn. Will definitely stay again!"

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."

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

7. BAYSIDE BUNGALOW

8. Cass-N-Reel Luxury Houseboat

9. Turtle Cove Room

10. Beachcomber Suite

11. Family Friendly Cozy 3 Bedroom Duplex

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

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

14. Turnbridge Manor

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

Hyatt Place Kent Narrows & Marina

The Inn at Chesapeake Bay Beach Club

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

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Frequently asked questions

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