Photo by Assya A

Search Chestertown Villa Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Chestertown Villas

Secluded Waterfront Retreat 2 bed 1 1/2 baths private guest house w Pool & Beach
Indoor pool

Secluded Waterfront Retreat 2 bed 1 1/2 baths private guest house w Pool & Beach

10.0 out of 10, Exceptional, (7)
Secluded Waterfront Retreat 2 bed 1 1/2 baths private guest house w Pool & Beach
Blake House Historic Estate with Private Inn
Relax by the pool surrounded by lush gardens and a classic two-story house.

Blake House Historic Estate with Private Inn

10.0 out of 10, Exceptional, (19)
"My family stayed at The Beach Club for our yearly vacation. In 6th"
Blake House Historic Estate with Private Inn
Stunning waterfront villa with indoor pool and kids swing set and play area.
Relax in the hot tub with a panoramic view of the lake.

Stunning waterfront villa with indoor pool and kids swing set and play area.

9.8 out of 10, Exceptional, (15)
"Wonderful location, lots to do, close to Chesapeake City, excellent host"
Stunning waterfront villa with indoor pool and kids swing set and play area.
Cozy Waterfront 3-bedroom villa with fitness/theater/game room, WiFi in Dundalk
Relax in the living area with a large sofa, coffee table, and flat-screen TV, plus a dining table and fireplace.

Cozy Waterfront 3-bedroom villa with fitness/theater/game room, WiFi in Dundalk

10.0 out of 10, Exceptional, (2)
"The property is clean, newly updated and spacious with an open concept floor plan. The A/C is more than adequate. The property is located on a picturesque inlet off of the bay with plenty of backyard space, a hot tub, decks with outdoor furniture and a game room downstairs."
Cozy Waterfront 3-bedroom villa with fitness/theater/game room, WiFi in Dundalk
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chestertown Hotel Reviews

The Inn at Henderson's Wharf, Ascend Hotel Collection

The Inn at Henderson's Wharf, Ascend Hotel Collection

10/10 Excellent
"Large, comfortable room."
Michael Paul 1-night trip
Posted 2 days ago
The Inn at Henderson's Wharf, Ascend Hotel Collection