1. Driftwood Inn

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Chestertown, MD

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Driftwood Inn

1.3 (15 reviews)
InexpensiveHotels
Open • Open 24 hours

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10 years ago

Rude as hell, couldn't even get a price before I was hung up on, because i repeated my self more then once.

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Brampton Bed and Breakfast Inn

Brampton Bed and Breakfast Inn

(48 reviews)

$$$

Brampton 1860 is one of those rare places that actually delivers on the promise of escape. From the…read moremoment we arrived, the world outside faded away. We stayed in Marley's Cottage and it was incredible. The red door entrance from our parking space felt like stepping into a secret hideaway. Inside we had a fireplace, a tub on the screened back patio, and a porch swing where we enjoyed our morning coffee. It was private, quiet, and felt like our own little world. Breakfast in the Manor House was outstanding with fresh eggs from their own chickens, and the daily afternoon tea became one of our favorite parts of the day. We met other guests, enjoyed fresh pastries, and had great conversations with the owners, Dave and Hilari. They are warm, welcoming, and clearly passionate about both hospitality and preserving the history of this place. Talking with them about Brampton's story and their vision was a highlight of our stay. Definitely try their Steampot dinner! It's loaded with fresh local seafood and felt like a true taste of the Eastern Shore. The property itself is beautiful to walk with gardens, meadows, and wildlife everywhere. Evenings by the fire pit were relaxing and made even better by Squeaky, the inn's charismatic cat. Brampton 1860 is the perfect spot for a romantic getaway or just time to slow down and recharge. Just search 'Brampton 1860 Better Living' to see our full review with more photos and details from our stay.

My fiancé and I had a terrible experience with the Brampton Inn as we tried to arrange an elopement…read morepackage there. The transaction should have been simple and straightforward. We were trying to solidify the plan in April/May for a mid-October elopement along with a several night stay in one of the cottages. What we received was lazy communication and terrible customer service. Nina is the employee to steer clear of. She alibied her piss poor responsiveness by saying the Eastern Shore culture just moved at a very slow pace. It took three attempts to receive an error-free contract. We had questions about the photographer that went unanswered for weeks. After nearly a month of trying to lock in our dates and address some of the finer details we received an email from Nina suggesting that we seek out another photographer or another venue altogether if they weren't moving fast enough for us. We did just that, refusing to beg anyone to take our money. Then today, three months later, we received an email from Nina asking us if we'd like to proceed. I responded to her email telling her we made other arrangements and that I'd be leaving feedback online about our experience with her. Attention David and Hillary Rinehart (owners), Nina is poorly representing your establishment and costing you money and your reputation.

Quality Suites

Quality Suites

(15 reviews)

$$

Okay, I probably should have done this 5 weeks ago, because this is my 5th Thursday I have stayed…read morehere...LOL!!! I'm not staying here because its a fantastic wonderful experience, but because it is the best deal in town. The rooms are clean and the place is quiet. On top of that the WiFi is decent; It will support streaming video from NetFlix and it connects just fine to my university's on-line classroom environment. I have not experience what Paul says about smoke in a smokeless room. Randall is correct, there is no exercise room at this facility, but they do have an indoor swimming pool. Chestertown is a quaint little town to run through and if you start at College and run to Water street, then west to the park and come up Cross Street and left onto High Street, then right onto Morgnec Rd, and then right onto 213 and back to the college, its about 3.75 miles. They do advertise a hot breakfast, and I looked at it once....only once...and past it by. I'm not in the mood for flying saucer / Frisbee eggs and greasy sausage patties from Sysco Institutional Food Services. Oh yes, they do have the fresh hot waffle too. Along with that they have a toaster and an assortment of bread, English muffins, and cheap frozen bagels, as well as some fresh fruit. Instead I've been going to Ellen's for good coffee and a fresh BLT w fried egg on toast sandwich. One word: BACON!!!! Yum!!!! LOL!! While I would have liked a nicer hotel, and I doubt the Holiday Inn next door is much better, as Chestertown is far off the beaten path. Not exactly what you would call a tourism center. Washington college brings parents for visits. At the end of October will be Down Rigging of the Tall Ships in the Chester River.

The first room we stayed in was infested with ants by the window sill, so they let us move to…read moreanother room. While the second room had a hint of smoke (although a smokeless hotel), we stuck around since the Holiday Inn next store was completely booked. Service was decent though and the room was pretty clean. Good amenities.

Hyatt Place Kent Narrows & Marina - Double room

Hyatt Place Kent Narrows & Marina

(22 reviews)

We had a great stay here and enjoyed the water views from our room and elsewhere in the hotel. The…read moreroom was great and everyone was very nice. The customer service was perfect. It was nice to be walking distance to restaurants and the Tiki Bar too. Two highlights of our trip were a visit to the Chesapeake Bay Environmental Center and a sightseeing cruise from Coastal Cruises who were docked at the hotel!

I decided to stay at this hotel for one night for a staycation away from DC. I chose this hotel…read morespecifically for its driveabilty from DC and for its beautiful view. I arrived late on Sunday evening on a cold and rainy night around 945pm. I was quickly checked in by Paul and also received a free upgrade. He was extremely personable and provided great customer service! I went over to the bar and saw signage that had a cocktail and mocktail as a fundraiser for Breast Cancer awareness month. The bartender on duty was Jamie. She wasn't as friendly as Paul. It was clear that her shift was ending at 10pm and she was already mentally checked out. When I inquired about the mockatil, she seemed annoyed. My hands were full of my bags so I informed her that I was running up to my room to drop off my bags and then I would come back to get my drink. She repeatedly reminded me that she is closing at 10pm which was 15 minutes away and she would be in the stock room. I felt pressured to pre purchase my drink before I went up to ensure it was made. I was up and back in 3 minutes and got my drink but didn't like the interaction with the bartender. The bar schedule has them closing at midnight but it seems they may close early when business is slow. Luckily there are a couple of restaurants in walking distance that stay open a little later as well. Theroom was beautiful, spacious and comfy. The marina view was beautiful at night and during the day. They have a great gym at the hotel as well which I was able to use for a great workout. Breakfast also seemed to have a great variety but I just grabbed some oatmeal to go. I was allowed a late checkout time 2pm due to my status but I left at 11am and decided to go do some shopping at the outlets before heading back home. I definitely plan to come back and stay here again and try out the boat happy hours and other activities in the area.

Great Oak Landing Lodge & Restaurant - Other end of resto

Great Oak Landing Lodge & Restaurant

(16 reviews)

If you want to escape the city life, drive 1.5 hours from Washington, D.C. to this 1940 manor along…read morethe bay. Inside a mansion that feels like a scene out of the Great Gatsby, Great Oak Manor was my home for a one-night stay on a Sunday to Monday. Here's my experience. 1) Check-In: Once you roll up, a sign directs you to their grand entrance. Park your car, check in, and someone on staff moves your car to the parking lot. Check in is smooth and comes with an old school room key and a card to access the wine area where you can enjoy several kinds of white and red wines. 2) Rooms: There are twelve rooms and suites inside the manor and one carriage house attached in the newer addition to the manor. I stayed on the second floor in the Marmaduke room with views of the water. It's a spacious room with a comfortable king bed, plenty of storage, strong WiFi, outlets everywhere, an iron, robes, and toiletries like mouth wash. The room lets in natural light and the blinds keep the light out at night. 3) Property: The manor comes with a library with many good reads and games. There's a bar and a dining room run by an award-winning chef that creates delicious breakfast, lunch, and dinner for guests. There's a snack area with coffee, snacks, chocolate, wine, and more that's open 14/7. Outside is a large lawn with outdoor games, a hammock, a fire pit, chairs, and a private beach. It's a perfect place to watch the sunset. 4) Service: Everyone I interacted with was professional, friendly, and remembered your name and story. I felt like family. 5) Area: Chestertown is 15 minutes away with lots of history, stores, and restaurants to explore.

8.3.26 - I placed a reservation for 2 days Mon-Wed. I was so excited to be getting away even for a…read morecouple days with my daughter. I booked this reservation through Expedia. I was sent the confirmation that stated I would only be charged for the added cancelation fee and would pay the remaining balance at the site. Within 1 day, the Lodge had placed a hole of over $200 on my credit card - the one I was NOT going to use for my stay. I was without those funds over an entire weekend. When I contacted the site 1st thing this AM I was told to calm down. The person I spoke with said I had spoken with her a couple weeks ago - I had not - which tells me they are having this happen frequently. It's a shame because this could have been a great get-a-way for us. Reservation canceled. Money refunded. Buyer beware!

Driftwood Inn - hotels - Updated October 2026

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