★★★★ 4-Star Luxury Hotel

Great Oak Manor

Chestertown  ·  United States  ·  10568 Cliff Road Chestertownmaryland 21620

4.8 376 guest reviews

About Great Oak Manor — Luxury Boutique Hotel in Chestertown

Great Oak Manor is an exceptional 4-star hotel in Chestertown, United States. Guests enjoy a distinctive experience combining world-class facilities including bar, concierge, fly fishing, and more with the personalised warmth that defines great boutique hospitality.

Guest Reviews 4.8 / 5

Brenda Gill
★★★★★ Apr 2025

The Great Oak Manor offers an exquisite blend of luxury, comfort, and charm. I have stayed at The Manor several times, and the experience has always been relaxing and rejuvenating. From the moment you arrive, the warm, welcoming ambiance greets you, and the attentive staff makes you feel right at home. The food is a highly curated gastronomic experience. I've never eaten an average meal here. I highly recommend you give it a try.

Matt Laken
★★★★★ Jul 2025

My wife and I went here for our recent BABYMOON. It was THE BEST! Our first evening we were greeting by a team featuring Brielle and Calin, a tremendous duo capable of satisfying even your most lavish of requests. A+++ Experience. Throughout our stay... We had THE MOST DELICIOUS dinner @ the Manor, made with the freshest of ingredients, presented in the most beautiful fashion. We enjoyed two breakfasts on site, both fresh and wonderful. We loved basking by the fire pits enjoying the magnificent grounds and sunsets/sunrises, we ventured to their private beach, another remarkable site to behold. Brielle and Calin, the nicest, kindest humans, looking out and thinking of everything you might need during your stay made it the most accommodating and great experience from check in to check out. The house is exquisite, the rooms are spacious and lavish, the grounds are kept up to perfection, we had THE BEST extended vacation here. Highly recommend, WILL return!

John Wasilisin
★★★★★ Mar 2025

This was our first visit to Great Oak Manor and we absolutely loved it! Starting with our phone call for a reservation with Corrine (who was lovely) to our arrival and weekend stay, we could not have felt more welcomed. Corrine, young Werten and Calin made us feel at home, and Mr. Werten (owner) was a pleasure to talk to. The morning breakfasts were delicious and the bar offers a wonderful way to ease into the evening. The grounds are lovely and the views of the Chesapeake Bay are terrific. We look forward to our next visit!