Vacation rentals in Chestertown

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Top-rated vacation rentals in Chestertown

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

Guest favourite

Home in Chestertown

4.94 out of 5 average rating, 127 reviews

CHESAPEAKE SUNSETS

Escape to a quaint bayside cottage with sweeping views of the Chesapeake. Relax and enjoy beautiful sunsets from the bayside sundeck, screened porch or from the comfort of your home. Less than 2 miles to the seasonal Shanty Bar at Tolchester Marina featuring live music, dining and its own beach. One mile from a private community boat ramp to launch your water toys. 800 sq ft 2 bedroom 1 bath house is on Maryland’s Eastern Shore less than 2 hours from Washington, Baltimore and Philadelphia.

Aug. 6 – 13

$304 CAD per night
Guest favourite

Home in Chestertown

5.0 out of 5 average rating, 150 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

$501 CAD per night
Guest favourite

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

$466 CAD per night

Popular amenities for Chestertown vacation rentals

Stay near Chestertown's top sights

Fish Whistle23 locals recommend
Luisa's Cucina Italiana27 locals recommend
Procolino's Pizza15 locals recommend
ACME Markets13 locals recommend
98 Cannon Riverfront Grille9 locals recommend
Uncle Charlie's Bistro15 locals recommend

Other great vacation rentals in Chestertown

Guest favourite

Casa particular in Chestertown

4.93 out of 5 average rating, 99 reviews

Red, White & Waterview Studio Apt with pool

Nov. 26 – Dec. 3

$200 CAD per night
Guest favourite

Home in Chestertown

4.96 out of 5 average rating, 69 reviews

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

Jan. 14 – 21

$302 CAD per night
Guest favourite

Home in Chestertown

4.98 out of 5 average rating, 40 reviews

2 Beds, 2.5 Baths, Perfect Downtown Location

May 8 – 15

$289 CAD per night
Guest favourite

Apartment in Chestertown

5.0 out of 5 average rating, 44 reviews

Bright, new apartment in the heart of Chestertown

Dec. 2 – 9

$324 CAD per night
Guest favourite

Home in Chestertown

4.88 out of 5 average rating, 25 reviews

Beautifully remodeled home in Historic Chestertown

Jun. 27 – Jul. 4

$271 CAD per night
Guest favourite

Home in Chestertown

5.0 out of 5 average rating, 23 reviews

125 High - Luxury Historical Brick Victorian

Aug. 6 – 13

$523 CAD per night
Guest favourite

Home in Chestertown

5.0 out of 5 average rating, 75 reviews

River front cottage with private dock & water fun

Apr. 5 – 12

$772 CAD per night
Guest favourite

Home in Chestertown

4.93 out of 5 average rating, 28 reviews

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

Oct. 7 – 14

$959 CAD per night
Guest favourite

Home in Chestertown

5.0 out of 5 average rating, 35 reviews

Waterfront house with private dock & kayaks!

Dec. 4 – 11

$386 CAD per night
Guest favourite

Home in Chestertown

5.0 out of 5 average rating, 14 reviews

Down by the River

Oct. 13 – 20

$1,143 CAD per night
Guest favourite

Home in Chestertown

5.0 out of 5 average rating, 50 reviews

Lovely, Recently-Renovated Home in Chestertown

Oct. 22 – 29

$278 CAD per night
Guest favourite

Home in Chestertown

5.0 out of 5 average rating, 23 reviews

Magnolia House ~Historic Downtown w/Private Garden

Dec. 18 – 25

$707 CAD per night

Quick stats about vacation rentals in Chestertown

Total rentals

50 properties

Wifi availability

50 properties include access to wifi

Rentals with dedicated workspaces

20 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

30 properties are a good fit for families

Total number of reviews

2.4K reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. Maryland
  4. Kent County
  5. Chestertown