Church Hill Holiday Rentals

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Holiday Rentals in Church Hill

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (36)
"Waterview cottage is comfortable and very clean. The accommodations look new and we had good sleep. The kitchen has most of the necessary equipment for meal preparation. A baking sheet pan is needed. WiFi and Roku TV was excellent. The primary bedroom bed was so tall/high my wife could not get in or out of it. That necessitated sleeping in the 2 twins. Plus, one of the twins was missing the top mini mattress. The view is mostly of the neighborhood street, nearby homes and their roofs and a small...
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (52)
"My family of 4 stayed here. So many things to do outside-truly a good time. So many games and accessories to have an easy good time. Would definitely stay at this place again."
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (16)
"We have been coming to Rock Hall for years and have stayed at the cottage the last two times and we have really enjoyed it. We will be back again and we will stay at this cottage again. My husband loves the sauna. Bill and Hannah"
The price is NZ$444
per night
2 Jun - 3 Jun
BAYSIDE BUNGALOW
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Retreat Near Dover
10.0 out of 10, Exceptional, (1)
"This house was the perfect affordable option for a coaching staff taking a team to the DE sport complex. Way more affordable than the hotels in the area and definitely cleaner. Beautiful field view in the back yard that reminded us of home. Will definitely go back!"
The price is NZ$741
per night
3 Jun - 4 Jun
Retreat Near Dover
Eastern Shore beach cottage get-away
10.0 out of 10, Exceptional, (122)
"The cozy cottage is perfectly maintained and well equipped. The bay view is as advertised and lovely. The location in Rock Hall is ideal, quiet and convenient to everything. The property manager is responsive and informative. We had a great, relaxing getaway weekend and look forward to returning."
Eastern Shore beach cottage get-away
Entire Townhouse in Rock Hall
10.0 out of 10, Exceptional, (15)
"We have stayed in this neighborhood before on a previous visit, we enjoyed how quiet and friendly the neighborhood is. We will definitely visit again. The house is very, very clean, cozy, and well stocked with all the supplies you could possibly need. We enjoyed sitting out in the evenings and watching the stars!!! Thanks for making our visit complete!!!"
Entire Townhouse in Rock Hall
Coastal Kent Narrows Home on Bay
10.0 out of 10, Exceptional, (4)
"Very nice place to stay, right on the bay"
Coastal Kent Narrows Home on Bay
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
9.8 out of 10, Exceptional, (14)
"We really enjoyed our (much too short) stay at this waterfront gem!! The property was very clean, had all the amenities that we needed for our time away.... the only complaint is that we didn't have enough time to enjoy it all!! : ) thank you so much, we will be back!"
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
9.8 out of 10, Exceptional, (80)
"House was fine. Odd they did not provide sheets. Was difficult for folks who came from far away. But the house was lovely and we enjoyed our time there!!"
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
10.0 out of 10, Exceptional, (19)
"Cozy & elegant ☀️ a clean bright space."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Cass-N-Reel Luxury Houseboat
10.0 out of 10, Exceptional, (11)
"We enjoyed the property and the proximity to bars/restaurants. We enjoyed the view from the back porch and it is a nice place to relax. We would definitely recommend staying and look forward to booking another stay in the future."
The price is NZ$595
per night
5 Jun - 6 Jun
Cass-N-Reel Luxury Houseboat
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
10.0 out of 10, Exceptional, (110)
"This is a great place to chill out with spectacular water views. The home has lots of wonderful spaces to hang out, read, watch TV, and look at the spectacular view. We also had fabulous canoe and kayak paddles up Cox Creek and adjacent waterways. Thanks Scott and Harry!"
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
First Floor Studio Apartment in Historic Chestertown
9.8 out of 10, Exceptional, (59)
"This was the perfect place to rest our heads along our trip down the east coast. Very comfortable, clean and quiet. We made time to visit the beautiful town and I’m glad we did!"
The price is NZ$268
per night
11 Jun - 12 Jun
First Floor Studio Apartment in Historic Chestertown
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
10.0 out of 10, Exceptional, (3)
"Lark’s Nest was a cute little place! Very clean! The view from the patio was stunning, and if you’re a bird lover you will be in your glory! Bring your binoculars and sit on the deck and wait! House was well equipped with most everything you would need! Host was very quick to write back when asked a question! First time in this area and hopefully be back again in the future!"
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Grasonville Home w/ Private Pool on the Water
10.0 out of 10, Exceptional, (12)
"We were in town for a family wedding. The house was spotless, well-stocked and centrally located for our trip. We recommend the property and would come again!"
Grasonville Home w/ Private Pool on the Water
Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |
10.0 out of 10, Exceptional, (3)
"Wonderful rental home for our family with great pool and river view. Swimming every day in the pool was so much fun for everyone, kayaks, and paddle boards were great since we did not have to bring anything. Children fished every night on the dock. We played lots of games inside and out everyday and enjoyed the Nature all around to see, birds, deer, fish, frogs and small animals. Our family felt like they had their own getaway for a wonderful vacation. Thank you for everything."
Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |
Waterfront home with private pier is A Shore Thing
10.0 out of 10, Exceptional, (15)
"The home and it's location were fantastic. Very clean and well-appointed. We enjoyed the layout and the space, and the view of the water was amazing in the Fall (kaledscope of colors)! Communication with the host was easy and prompt. Highly recommend and we will be back!"
Waterfront home with private pier is A Shore Thing
Guest Suite for up to 2 in a Victorian on the Chester River
The price is NZ$204
per night
10 Jun - 11 Jun
Guest Suite for up to 2 in a Victorian on the Chester River
200 steps to the beach!
10.0 out of 10, Exceptional, (75)
"Great stay over Memorial Day weekend. Loved the location of the house...so close to the water and not crowded at all. We will definitely be back!"
200 steps to the beach!
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
10.0 out of 10, Exceptional, (28)
"I organized a large (15 person) bachelorette weekend at this property in early April. It is an absolutely gorgeous house and the host had a number of thoughtful touches - like extra firewood for the firepit, coffee supplies, and a bottle of bubbly for our bride! The beds were comfortable (even the twins!), which was lucky because one bedroom on the breakdown was not really usable, so a handful of guests relocated to one of the 'kid rooms.' We found Ashleigh very responsive both before and...
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Don't see what you're looking for?
See all available properties in Church Hill
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.

Other types of properties in Church Hill you may be interested in

Hyatt Place Kent Narrows & Marina
3.0 star property
9.4 out of 10, Exceptional, (313)
"We had a great time! Staff were friendly. There are a few nice restaurants within walkable distance. A fishing pier is next to it. A good place for a weekend getaway!"
The price is NZ$346
per night
10 Jun - 11 Jun
Hyatt Place Kent Narrows & Marina
Best Western Kent Narrows Inn
2.5 star property
8.0 out of 10, Very good, (1000)
"Unfortunately I fell in an extremely slippery bathtub. The apparently recently recoated tub surface combined with bath products containing argon oil combined to make the surface of the tub like ice. Our stay otherwise was quite pleasant."
The price is NZ$231
per night
10 Jun - 11 Jun
Best Western Kent Narrows Inn
Hilton Garden Inn Kent Island
3.0 star property
9.0 out of 10, Wonderful, (774)
"Hotel I had a wonderful stay bay front view was awesome. Hotel staff was very polite and professional. Very convenient location next to the Jetty one if my favorite spots with outside seating. Will stay again and would definitely recommend to everyone. "
The price is NZ$367
per night
13 Jun - 14 Jun
Hilton Garden Inn Kent Island
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Church Hill holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Church Hill. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Church Hill. Seeing all the best attractions is bound to make you fall in love with Church Hill. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Church Hill short-term rentals, that won’t be hard to do.

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?

Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.: This holiday home rental outside of Church Hill is located on the waterfront, and has a private balcony, a private garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

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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