Holiday houses in Chestertown

Find and book unique accommodation on Airbnb

Top-rated accommodation 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.

7–14 Aug

$374 NZD per night
Guest favourite

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.

2–9 Aug

$356 NZD 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.

28 Sep – 5 Oct

$573 NZD per night

Popular amenities for Chestertown accommodation

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 accommodation in Chestertown

Guest favourite

Casa particular in Chestertown

4.93 out of 5 average rating, 99 reviews

Red, White & Waterview Studio Apt with pool

27 Nov – 4 Dec

$247 NZD 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

15–22 Jan

$374 NZD per night
Guest favourite

Home in Chestertown

4.98 out of 5 average rating, 40 reviews

2 Beds, 2.5 Baths, Perfect Downtown Location

8–15 May

$356 NZD per night
Guest favourite

Home in Chestertown

4.88 out of 5 average rating, 25 reviews

Beautifully remodeled home in Historic Chestertown

24 Jun – 1 Jul

$333 NZD per night
Guest favourite

Apartment in Chestertown

5.0 out of 5 average rating, 44 reviews

Bright, new apartment in the heart of Chestertown

17–24 Jun

$535 NZD per night
Guest favourite

Home in Chestertown

5.0 out of 5 average rating, 23 reviews

125 High - Luxury Historical Brick Victorian

5–12 Feb

$644 NZD per night
Guest favourite

Home in Chestertown

5.0 out of 5 average rating, 75 reviews

River front cottage with private dock & water fun

5–12 Apr

$950 NZD per night
Guest favourite

Home in Chestertown

4.93 out of 5 average rating, 28 reviews

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

7–14 Oct

$1,195 NZD per night
Guest favourite

Home in Chestertown

5.0 out of 5 average rating, 35 reviews

Waterfront house with private dock & kayaks!

4–11 Dec

$477 NZD per night
Guest favourite

Home in Chestertown

5.0 out of 5 average rating, 14 reviews

Down by the River

14–21 Oct

$1,406 NZD per night
Guest favourite

Home in Chestertown

5.0 out of 5 average rating, 50 reviews

Lovely, Recently-Renovated Home in Chestertown

22–29 Oct

$343 NZD per night
Guest favourite

Home in Chestertown

5.0 out of 5 average rating, 23 reviews

Magnolia House ~Historic Downtown w/Private Garden

18–25 Dec

$870 NZD per night

Quick stats about accommodation in Chestertown

Total rentals

50 properties

Wi-Fi availability

50 properties include access to Wi-Fi

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