Vacation rentals in Kingstown

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Kingstown

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

Guest favorite

Apartment in Chestertown

4.97 out of 5 average rating, 188 reviews

Quiet escape in center of town

Escape to a secluded, romantic studio hideaway in the middle of Chestertown. Private parking, and over 1 acre of gardens to call your own. Relax in front of the fire with views of gardens in every window. Kitchenette has extra large toaster oven, (can cook pizza and roast chicken), 2 burner hot plate, microwave, refrigerator, and Keurig/coffee makers. Comfortable king bed with luxury linens, kitchenette, and washer dryer. We also host ‘Wren Retweet”, a house in front of the carriage house.

Aug 2 – 9

R3,834 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.

Sep 28 – Oct 5

R5,846 ZAR per night
Guest favorite

Guest suite in Chestertown

4.99 out of 5 average rating, 126 reviews

Chestertown - Eastern Shore Getaway

"A little slice of Americana" (commented one of our guests) This century-old three-story home is in the beautiful historic district of Chestertown, which sits on the majestic, unspoiled Chester River, on Maryland's famous Eastern Shore. We are right across the street from Washington College and just blocks from the quaint ambiance of High Street. The commercial district is equally accessible, with banks, grocery and liquor stores, restaurants, and more, a few blocks up Washington Avenue.

Aug 19 – 26

R2,756 ZAR per night

Popular amenities for Kingstown vacation rentals

Stay near Kingstown's top sights

Fish Whistle23 locals recommend
98 Cannon Riverfront Grille9 locals recommend
Dollar General6 locals recommend
Chester River Packet Company12 locals recommend
Women In Need Inc3 locals recommend
Bohemia Trading Company4 locals recommend

Other great vacation rentals in Kingstown

Guest favorite

Guest suite in Chestertown

4.93 out of 5 average rating, 45 reviews

Historic Downtown Garden Oasis with Private Patio

Oct 7 – 14

R3,135 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

Home in Chestertown

4.96 out of 5 average rating, 69 reviews

Cozy 3-bedroom home w/ screened in porch & firepit

Jan 15 – 22

R3,761 ZAR per night
Guest favorite

Home in Chestertown

4.98 out of 5 average rating, 40 reviews

2 Beds, 2.5 Baths, Perfect Downtown Location

May 8 – 15

R3,507 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

Home in Chestertown

5.0 out of 5 average rating, 23 reviews

125 High - Luxury Historical Brick Victorian

Feb 5 – 12

R6,527 ZAR per night
Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 14 reviews

Down by the River

Oct 14 – 21

R15,147 ZAR per night
Guest favorite

Apartment in Chestertown

5.0 out of 5 average rating, 44 reviews

Bright, new apartment in the heart of Chestertown

Jun 17 – 24

R5,595 ZAR per night
Guest favorite

Home in Chestertown

4.88 out of 5 average rating, 25 reviews

Beautifully remodeled home in Historic Chestertown

Jun 24 – Jul 1

R3,387 ZAR per night
Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 23 reviews

Magnolia House ~Historic Downtown w/Private Garden

Dec 18 – 25

R8,894 ZAR per night
Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 19 reviews

In Town Chestertown Rancher (1 Block to College)

Jun 5 – 12

R4,296 ZAR per night
Guest favorite

Apartment in Chestertown

4.92 out of 5 average rating, 62 reviews

1-br apt in downtown Chestertown

Jun 10 – 17

R4,037 ZAR per night

Destinations to explore