Chestertown Villas & Villa Rentals

Find villas near Chestertown - We found 165 exact matches

About Chestertown Villa on Hotala

In addition to hotels and resorts, Hotala has more than 165 villas near Chestertown. These rentals have all the luxury accoutrements to give you comfort, including amenities such as - private swimming pools, WIFI, spas, hot tubs, and more.

Hotala has a wide range of private villa rentals near Chestertown, and there are different options for families, friends, or even couples. These villas and resort villas come in unique styles or sizes that would definitely suit your needs.

Hotala offers expectational rental villas that are out of the ordinary and not found elsewhere, whether you are traveling on a beachfront, seaside, mountain, or any destination. Hotala is an all-in-one travel platform that matches you with the perfect rental villa in Chestertown for your dream vacation. Discover last minute and the best villa deals with Hotala

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Frequently Asked Questions About Chestertown Rental Villas

There are a lot of options in Chestertown. If you plan on staying in the Chestertown area, consider making a reservation for a few nights at one of these properties as these have been rated the top Villa Rentals in Chestertown:

At Hotala, the average rental fee for standard villas in Chestertown is $370 per night. Hotala has a large database of quality villas near Chestertown that are suitable for families, a romantic getaway, or a solo trip with single or multiple bedrooms.
Yes, here are the top villas rentals in Chestertown that are pet friendly:See all pet-friendly vacation rentals in Chestertown on Hotala
Most of our listed villas are suitable for families. The number of rooms varies, and you can check out the complete list of villas in Chestertown to find what works for you.
Based on the 2025 data from our Hotala site, there are more than 165 private swimming pools or villas with indoor pools in or near Chestertown.
There are 165 villas in or near Chestertown that have hot tubs. The most popular places to stay with hot tubs include:See all holiday vacation rentals in Chestertown on Hotala
Most definitely! There are many luxury villas in Chestertown. Use our search filter to discover all of our luxury villas, and choose the one that matches your taste. Sorting by price is another way to find the most expensive villas in Chestertown.