Church Hill Vacation Rentals

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Check prices for these dates

Tonight
Jul 23 - Jul 24
Tomorrow
Jul 24 - Jul 25
This weekend
Jul 25 - Jul 27
Next weekend
Aug 1 - Aug 3

Vacation Rentals in Church Hill

Cass-N-Reel Luxury Houseboat
Marina

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (31)
"We really enjoyed our stay. Looking forward to staying again!"
Cass-N-Reel Luxury Houseboat
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, (6)
"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
BAYSIDE BUNGALOW
Sauna

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (42)
"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 ￥29,320
￥44,288 total
includes taxes & fees
Jul 27 - Jul 28
BAYSIDE BUNGALOW
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, (52)
"I loved the property. The cottage was super clean, tidy and extremely relaxing. Super close to the water, & the views were spectacular. I went for the serenity to fly my drone and capture some great footage. And I certainly was not disappointed . Chris made the check in super easy, with great communication. I absolutely will return. 10 out of 10 rating."
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, (41)
"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
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, (188)
"We all had wonderful stay at Love point! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (91)
"Very pretty location. Few minutes drive to town center."
The price is ￥14,593
￥23,413 total
includes taxes & fees
Aug 4 - Aug 5
First Floor Studio Apartment in Historic Chestertown
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, (5)
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, (18)
"Loved the location, the property, and amenities. Would definitely stay again!"
The price is ￥65,838
￥113,144 total
includes taxes & fees
Aug 2 - Aug 3
Waterfront Sunset Bayview: sleeps 6
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
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 - 6 Guests
Smart TV, fireplace

RELAX- Eastern Shore Creek Home - 6 Guests

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 - 6 Guests
Waterfront Retreat with Private Dock and Beach
Beach

Waterfront Retreat with Private Dock and Beach

10.0 out of 10, Exceptional, (21)
"I stayed with 3 friends and it was lovely! The apartment was clean and tidy. The view was spectacular. The host was very communicative and kind leading up to and during our stay. There are great restaurants and things to do in the area as well. "
The price is ￥32,985
￥55,500 total
includes taxes & fees
Jul 27 - Jul 28
Waterfront Retreat with Private Dock and Beach
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, (8)
"Had a very comfortable stay here. Very clean and the towels to kill for (ha). Ms. Lynn kept in touch at all times. I would stay here again for sure."
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
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, (10)
"Perfection"
The price is ￥18,178
￥43,206 total
includes taxes & fees
Jul 27 - Jul 28
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
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, (123)
"Nice big home with lots of room to be together"
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
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, (7)
"This home was perfect for our 3 night stay. We came to spend time with our daughter who had moved to the area. The owners thought of everything and the little touches are what made this the perfect rental for our stay. Only downside was the weather did not allow us to enjoy the amazing views and cozy porches during our stay. Next time we visit with a group we will definitely stay here again!"
Island Blue Getaway! Brand new charming family friendly Home on Kent Island MD
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, (6)
"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 ￥28,895
￥65,283 total
includes taxes & fees
Jul 28 - Jul 29
HGTV quality, private guest suite, country getaway with hot tub & fire pit
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (43)
"This property was perfect for our trip. It was very clean, comfortable and feels like home. Description and photos on the website were accurate. The owners were very attentive and hospitable. This is definite a place I’ll return to."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
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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Top Church Hill Hotel Reviews

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

10/10 Excellent
"Great Experience !! "
James 3-night trip
Posted 12 hours ago
Hilton Garden Inn Kent Island Marina

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?

Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets: This vacation home near 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 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 a family-friendly sight such as Hazel Miner Monument. 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.