Church Hill Holiday Rentals

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Check prices for these dates

Tonight
12 Jul - 13 Jul
Tomorrow
13 Jul - 14 Jul
Next weekend
18 Jul - 20 Jul
In two weeks
25 Jul - 27 Jul

Holiday Rentals in Church Hill

Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets
Dining

Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

10.0 out of 10, Exceptional, (5)
"Relaxing and stunning location. Beautiful bay front property with stunning views of the bay. If you are looking for a quiet and peaceful getaway that involves wildlife sightings this is the perfect spot. Well equipped and roomy rental. Very clean too. "
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets
Cass-N-Reel Luxury Houseboat
Marina

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (30)
"We really enjoyed our stay. Looking forward to staying again!"
The price is HK$848
HK$2,172 total
includes taxes & fees
24 Jul - 25 Jul
Cass-N-Reel Luxury Houseboat
BAYSIDE BUNGALOW
Sauna

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (41)
"Beautiful, cozy cottage. So peaceful and pretty. Owners are on site and are great people. We have stayed here several times and look forward to coming back soon."
The price is HK$1,570
HK$2,363 total
includes taxes & fees
14 Jul - 15 Jul
BAYSIDE BUNGALOW
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (90)
"Very pretty location. Few minutes drive to town center."
The price is HK$777
HK$1,247 total
includes taxes & fees
17 Jul - 18 Jul
First Floor Studio Apartment in Historic Chestertown
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Outdoor dining

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

10.0 out of 10, Exceptional, (187)
"We all had wonderful stay at Love point! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Exterior

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

10.0 out of 10, Exceptional, (4)
"My kids and I absolutely loved our stay at the Outlook! So peaceful and relaxing. We spent a lot of time walking around the trails spotting deer and toads. We did a good amount of fishing on the dock, catching catfish. I hope to stay here again in the future."
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Waterfront Sunset Bayview: sleeps 6
Terrace/patio

Waterfront Sunset Bayview: sleeps 6

10.0 out of 10, Exceptional, (17)
"Loved the location, the property, and amenities. Would definitely stay again!"
The price is HK$3,917
HK$6,524 total
includes taxes & fees
2 Aug - 3 Aug
Waterfront Sunset Bayview: sleeps 6
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Smart TV, books

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (51)
"This was our second time staying at the property with our two kids and the accommodations continue to impress. We will happily stay again."
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Beach nearby, sun-loungers, beach towels

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

9.6 out of 10, Exceptional, (40)
"This is the second time my husband and I have stayed here. Despite a mixed bag of weather ranging from snow, rain, winds, and sunshine, the visit did not disappoint. We were still able to walk on the beach, view the resident bald eagle, immerse ourselves in the ever changing water views and visit surrounding towns.The house was warm and welcoming."
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC
Dining

Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC

9.8 out of 10, Exceptional, (12)
"We loved the property and the excellent way the owners took care of it"
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC
RELAX- Eastern Shore Creek Home
Smart TV, fireplace

RELAX- Eastern Shore Creek Home

10.0 out of 10, Exceptional, (2)
"Great property that is well kept. It is a short drive to several wonderful restaurants and an outlet shopping center."
RELAX- Eastern Shore Creek Home
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
1 bedroom, bed sheets

The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE

9.8 out of 10, Exceptional, (7)
"Located in a quite area and the host were incredible"
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
Waterfront Retreat with Private Dock and Beach
Beach

Waterfront Retreat with Private Dock and Beach

10.0 out of 10, Exceptional, (21)
"Everything about the place was great! Easy check in and super clean and homey feeling spot. Would recommend to anyone looking for a quiet and comfy place on the eastern shore. We will definitely be booking again if we come back to the area!"
The price is HK$1,766
HK$2,955 total
includes taxes & fees
14 Jul - 15 Jul
Waterfront Retreat with Private Dock and Beach
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Fridge, microwave, oven, stovetop

Secluded Waterfront Cottage on 200 acre farm near Queenstown

10.0 out of 10, Exceptional, (101)
"My family and I had a ball, enjoyed our time on the water and hanging out on the farm. "
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Fridge, microwave, stovetop, dishwasher

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

10.0 out of 10, Exceptional, (122)
"Nice big home with lots of room to be together"
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Terrace/patio

HGTV quality, private guest suite, country getaway with hot tub & fire pit

10.0 out of 10, Exceptional, (5)
"Was looking for an upscale beautiful place to stay for a family wedding. Found it! Tammy has tended to every detail at this VRBO. Gorgeous farmhouse chic. Very attentive to our texts. And always good to return to Centreville to see friends and family. "
The price is HK$1,547
HK$3,496 total
includes taxes & fees
15 Jul - 16 Jul
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Island Blue Getaway! Brand new charming family friendly Home on Kent Island MD
Interior

Island Blue Getaway! Brand new charming family friendly Home on Kent Island MD

10.0 out of 10, Exceptional, (6)
"Loved our stay in this beautiful home. We were in town for a wedding at the nearby Chesapeake Beach Club. It was so quick & easy to get there from the house. It was wonderful to have an entire house to get ready for the wedding rather than in a hotel room. The Hosts did a great job with providing everything you need in this home. Highly recommend this home!! Everything about it was amazing!!"
Island Blue Getaway! Brand new charming family friendly Home on Kent Island MD
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Beach

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

10.0 out of 10, Exceptional, (8)
"Perfection"
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Historic Downtown Garden Oasis with Private Patio
Property grounds

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (35)
"Lovely place to stay in downtown Chestertown. So close to walk to eating, shopping and events. Had many great amenities to make the stay comfortable. Host was very communicative and quick to respond. "
Historic Downtown Garden Oasis with Private Patio
Grasonville Home w/ Private Pool on the Water
Pool

Grasonville Home w/ Private Pool on the Water

10.0 out of 10, Exceptional, (21)
"Location was great for our stay"
Grasonville Home w/ Private Pool on the Water
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.
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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?

Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets: This holiday home rental outside of Church Hill is equipped with a patio, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms, as well as a kitchen with a dishwasher, a microwave and a coffee maker, so that you can cook with friends or family.

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 Hazel Miner Monument. 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.