Compare Chestertown Villas

Featured Villas in Chestertown

Guests staying at this villa can enjoy an indoor pool, barbecue grills, and a garden.

Pool

Kitchen

Blake House Historic Estate with Private Inn

$3,344 nightly

$3,483 total

Jul 30 - Jul 31

Total includes taxes and fees

At this villa, guests have access to a gym, laundry facilities, and barbecue grills. This smoke-free villa also has a garden.

Pool

Kitchen

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

Guests staying at this vacation home enjoy a gym, an arcade/game room, and laundry facilities. This family-friendly vacation home also has a garden.

Kitchen

Washer

Guests of this villa enjoy features like an indoor pool, a hot tub, and an arcade/game room. Other amenities at this family-friendly villa include laundry facilities and barbecue grills.

Pool

Hot Tub

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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.

Hotel Options in Chestertown

Comfort Inn & Suites Chestertown

150 Scheeler Road, Chestertown, MD

$111 nightly

$124 total

Aug 17 - Aug 18

Total includes taxes and fees

8.4/10 Very Good! (778 reviews)

Red Roof Inn & Suites Chestertown

160 Scheeler Rd, Chestertown, MD

$68 nightly

$76 total

Jul 23 - Jul 24

Total includes taxes and fees

7.2/10 Good! (374 reviews)

The Lodge at Great Oak Landing

22170 Great Oak Landing Rd, Chestertown, MD

$147 nightly

$163 total

Jul 20 - Jul 21

Total includes taxes and fees

7.8/10 Good! (53 reviews)

Luxury Villas

Book luxury villas in Chestertown
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in Chestertown. Villas, with their thoughtful layout and elegant décor, let you travel in style. They come in a variety of sizes and offer a great experience, whether you’re traveling on your own or with a group of friends. Orbitz has fantastic deals on villas in Chestertown, so book one now. You’ll feel like a million bucks before you even check in.

Spacious luxury villas in Chestertown
You won’t have a problem finding your own space in Chestertown. If you’re traveling in a group, go for a three-bedroom or larger villa; separate bedrooms can make it that much easier to keep the peace, especially when you’re all staying in one house. You can also explore Chestertown on your own and use a one-bedroom villa as your home base.

A top-end villa experience in Chestertown rivals that of a luxury resort. Float in a swimming pool with an elaborate mosaic bottom, work out in your own gym, and let the daily housekeeping staff clean up after you while a private chef whips up one delicious meal after another. This is the life!

Chestertown Villas essential information

Accommodation	4 Villas
Lowest Price	$76
Highest Price	$3,483
Popular accommodation	Secluded Waterfront Retreat 2 bed 1 1/2 baths private guest house w Pool & Beach, Blake House Historic Estate with Private Inn, Cozy Waterfront 3-bedroom villa with fitness/theater/game room, WiFi in Dundalk, Stunning waterfront villa with indoor pool and kids swing set and play area.