Vacation rentals in Church Hill

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Top-rated vacation rentals in Church Hill

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Farm stay in Chestertown

4.94 out of 5 average rating, 106 reviews

Outrange at Blue Heron Farm

Enjoy the peace and tranquillity at “Outrange,” Blue Heron Farm’s recently updated cabin. This unique and rustic 2 bedroom, 1 bath home was designed by architect Randy Wagner and built in 1978. Tucked away on a 126 acre fourth-generation organic waterfront farm, Outrange is a private getaway situated just 15 minutes from historic Chestertown. With views of the Chester River and access to the farm’s private dock, Outrange is a magical getaway for anyone that loves the beauty of the Eastern Shore.

Apr 12 – 19

R4,414 ZAR per night
Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 151 reviews

Historic house, near town center, pet friendly

Renovated 19th century home with all modern conveniences. First floor bedroom with private bath. Hi speed internet. Pets welcome! Located in the historic district of Chestertown, a 3 block walk from both Washington College and the C'town waterfront. 2 primary bedroom suites (one on the second floor has a king bed) 2 more bedrooms with queen beds. 1 loft which is connected to the a 2nd story bedroom has 2 twins. Fenced yard and over an acre of totally private gardens. Fire pit.

Dec 10 – 17

R6,638 ZAR per night
Guest favorite

Cabin in Chestertown

4.98 out of 5 average rating, 215 reviews

Rivershore Retreat

Escape to Maryland’s Eastern Shore where the pace of life is slower and nature surrounds you. Mid-century modern A-frame with artfully curated décor and a well-appointed kitchen has drop-dead gorgeous river views and its own waterfront and dock. The house sits on a large, private acre lot with plenty of room for kids to play. Short walk to downtown Chestertown with its Farmer’s Market, restaurants and galleries. A perfect get-away for artists, writers or families seeking a low-key vacation.

Apr 4 – 11

R5,846 ZAR per night

Popular amenities for Church Hill vacation rentals

Other great vacation rentals in Church Hill

Guest favorite

Farm stay in Centreville

4.96 out of 5 average rating, 51 reviews

3 bedroom home with pool and game room

Oct 1 – 8

R4,509 ZAR per night
Guest favorite

Home in Greensboro

4.95 out of 5 average rating, 44 reviews

Cozy 2 bedroom home on wooded private lane

Feb 5 – 12

R2,434 ZAR per night
Superhost

Guesthouse in Centreville

4.83 out of 5 average rating, 71 reviews

Centreville Cottage

Sep 12 – 19

R2,904 ZAR per night
Guest favorite

Apartment in Chestertown

4.92 out of 5 average rating, 95 reviews

Downtown Studio Apartment

Jan 4 – 11

R2,610 ZAR per night
Guest favorite

Guesthouse in Wye Mills

4.93 out of 5 average rating, 15 reviews

Adorable Lake Front 1BR Cottage-fully furnished!

Sep 23 – 30

R1,645 ZAR per night
Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 75 reviews

River front cottage with private dock & water fun

Apr 5 – 12

R9,799 ZAR per night
Guest favorite

Apartment in Dover

4.88 out of 5 average rating, 84 reviews

Cozy apartment in a quiet Amish country setting

Feb 1 – 8

R1,638 ZAR per night
Guest favorite

Home in Church Hill

4.94 out of 5 average rating, 47 reviews

Private Peaceful Waterfront House w/ Pool, Hot Tub

Mar 18 – 25

R12,110 ZAR per night
Guest favorite

Home in Chestertown

4.93 out of 5 average rating, 28 reviews

Harbor View Haven | Waterfront w/ HOT TUB + Dock!

Oct 7 – 14

R11,729 ZAR per night
Guest favorite

Cottage in Charlestown

4.98 out of 5 average rating, 43 reviews

Long Beach Cottage, (romantic couple’s getaway)

Nov 26 – Dec 3

R8,771 ZAR per night
Guest favorite

Apartment in Kent County

4.92 out of 5 average rating, 73 reviews

Furnished country apartment!

Oct 24 – 31

R1,881 ZAR per night
Guest favorite

Home in Millington

4.91 out of 5 average rating, 32 reviews

The Peaceful Getaway (with private pool & hot tub)

Jul 5 – 12

R8,169 ZAR per night

Destinations to explore