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Church Hill Vacation Rentals

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Church Hill vacation rentals

Property grounds

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (118 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is ￥16,209
￥26,007 total
includes taxes & fees
Aug 3 - Aug 4
First Floor Studio Apartment in Historic Chestertown
Exterior

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

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.8 out of 10, Exceptional, (23 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
The price is ￥11,134
￥20,480 total
includes taxes & fees
Aug 10 - Aug 11
Guest Suite for up to 2 in a Victorian on the Chester River
TV, fireplace

Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
The price is ￥30,061
￥45,727 total
includes taxes & fees
Jul 29 - Jul 30
Secluded Cottage in Middle of Chestertown
Beach

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

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (27 reviews)
"This is an excellent cute little bungalow close to the beautiful town of Rock Hall. My wife and I enjoyed this very clean and neat place to stay while we enjoyed visiting our family. The host keeps everything very well kept on this property for his visitors! Highly recommend!!"
United States
DEAN
The price is ￥19,287
￥46,433 total
includes taxes & fees
Jul 29 - Jul 30
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Property grounds

Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"The house was lovely, very comfortable and hosts were very responsive! We will be back for another stay. "
United States
Diana S.
The price is ￥62,951
￥94,446 total
includes taxes & fees
Jul 30 - Jul 31
Wren Retweet- Country Estate in Center of C’Town
Property grounds

Beachcomber Suite

Beachcomber Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"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...
United States
Lisa E.
The price is ￥23,872
￥29,665 total
includes taxes & fees
Aug 10 - Aug 11
Beachcomber Suite
WiFi, bed sheets

Turtle Cove Room

Turtle Cove Room
Kent County
The price is ￥22,988
￥28,527 total
includes taxes & fees
Aug 3 - Aug 4
Turtle Cove Room
Exterior detail

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (60 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is ￥32,746
￥49,636 total
includes taxes & fees
Jul 29 - Jul 30
BAYSIDE BUNGALOW
Beach nearby

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (26 reviews)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is ￥36,839
￥61,985 total
includes taxes & fees
Aug 4 - Aug 5
Waterfront Retreat with Private Dock and Beach
Smart TV

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (4 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is ￥28,653
￥59,529 total
includes taxes & fees
Jul 29 - Jul 30
Bayside Cottage steps from Rock Hall Harbor
Interior

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

Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
Dover
9.8 out of 10, Exceptional, (9 reviews)
"Woodland Hideaway was just that! A nice place to hideaway after hot and busy days. The place was clean, kitchen well stocked and the whole unit was quiet. It was located in a nice subdivision with lots of trees and beautiful flowers. It was the first trip my husband and I took our dog and it was a great place for the dog, quiet with lots of places for his daily walks. Thank you Kara!"
United States
Melanie
The price is ￥19,648
￥30,847 total
includes taxes & fees
Aug 13 - Aug 14
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
Dining

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

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (15 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
The price is ￥40,933
￥68,554 total
includes taxes & fees
Jul 29 - Jul 30
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
House (3 Bedrooms) | Interior

Dover Home Base: 3 Mi to Motor Speedway!

Dover Home Base: 3 Mi to Motor Speedway!
3.0 star property
Dover
The price is ￥19,987
￥70,091 total
includes taxes & fees
Aug 2 - Aug 3
Dover Home Base: 3 Mi to Motor Speedway!
TV, computer monitors

Dover Home Base: 3 Mi to Motor Speedway!

Dover Home Base: 3 Mi to Motor Speedway!
Dover
9.0 out of 10, Wonderful, (7 reviews)
"Great property in a quiet neighborhood. Owner communicated easily and effectively. "
United States
Patrick C.
The price is ￥13,917
￥72,197 total
includes taxes & fees
Aug 2 - Aug 3
Dover Home Base: 3 Mi to Motor Speedway!
Property grounds

Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (15 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is ￥58,943
￥99,794 total
includes taxes & fees
Aug 10 - Aug 11
Turnbridge Manor
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

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent
"We liked all that the hotel offered"
robert 1-night trip
Posted 2 hours ago
The Inn at Chesapeake Bay Beach Club

Find out more about Church Hill

Search for holiday rentals in Church Hill on Expedia! You can easily find your home rentals, villas, holiday apartments in Church Hill using one of the methods below:

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Look no further and take a look at our great range of rental properties in Church Hill!

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?

Pool + Hot Tub + Pickleball | Waterfront: This highly rated vacation home rental in Church Hill is located on a river and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub.

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.