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Church Hill Holiday Rentals

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Check prices for these dates

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

Our top choices for Church Hill holiday 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 HK$776
HK$1,246 total
includes taxes & fees
3 Aug - 4 Aug
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 HK$533
HK$981 total
includes taxes & fees
29 Jul - 30 Jul
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 HK$1,440
HK$2,190 total
includes taxes & fees
29 Jul - 30 Jul
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)
"Kitchen was fully stocked, apartment very clean, very nice host and parking was great"
United States
Tara K.
The price is HK$924
HK$2,232 total
includes taxes & fees
29 Jul - 30 Jul
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 HK$3,015
HK$4,524 total
includes taxes & fees
30 Jul - 31 Jul
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 HK$1,143
HK$1,421 total
includes taxes & fees
10 Aug - 11 Aug
Beachcomber Suite
WiFi, bed sheets

Turtle Cove Room

Turtle Cove Room
Kent County
The price is HK$1,101
HK$1,366 total
includes taxes & fees
10 Aug - 11 Aug
Turtle Cove Room
Exterior detail

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (59 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is HK$1,568
HK$2,377 total
includes taxes & fees
2 Aug - 3 Aug
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 HK$1,765
HK$2,969 total
includes taxes & fees
29 Jul - 30 Jul
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 HK$1,670
HK$3,209 total
includes taxes & fees
25 Aug - 26 Aug
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 HK$941
HK$1,454 total
includes taxes & fees
27 Aug - 28 Aug
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 HK$1,960
HK$3,283 total
includes taxes & fees
29 Jul - 30 Jul
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
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 HK$957
HK$3,355 total
includes taxes & fees
2 Aug - 3 Aug
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 HK$667
HK$3,458 total
includes taxes & fees
2 Aug - 3 Aug
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 HK$2,823
HK$4,780 total
includes taxes & fees
10 Aug - 11 Aug
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

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent
"Great location and nice staff!"
Amit 2-night trip
Posted 6 hours ago
Holiday Inn Express Annapolis East-Kent Island by IHG

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:

  • View our selection of featured holiday rentals in Church Hill
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  • Enter your travel dates to view the best deals on holiday rentals in Church Hill while they last

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

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?

Pool + Hot Tub + Pickleball | Waterfront: This highly rated holiday home rental in Church Hill is located on a river, and has a balcony, a garden and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

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.