"Nice clean place and priced good. Plenty of mirrors, plenty of counter space, many tv channels even Christian based ones and comfortable bed.
The room needs up dating since damage area on ceiling and corner location rug worn spot.
I felt safe as a solo, could check in late and close to historic Chestertown.
I would come again."
"Nice clean place and priced good. Plenty of mirrors, plenty of counter space, many tv channels even Christian based ones and comfortable bed.
The room needs up dating since damage area on ceiling and corner location rug worn spot.
I felt safe as a solo, could check in late and close to historic Chestertown.
I would come again."
"Enjoyable stay. All was as advertised. The host was very helpful when asked for information. Location was wonderful, very central in the old part of town. We had a great time!"
"Enjoyable stay. All was as advertised. The host was very helpful when asked for information. Location was wonderful, very central in the old part of town. We had a great time!"
"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...
"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...
"The property was stunning. The rooms were very comfortable and the bathroom had all you need. We also really appreciated the drinks and free salted chocolate chip cookies. They were delicious. The inn keepers were and their dogs were a highlight for us.
The breakfast was also absolutely delicious. Definitely would recommend this I"
"The property was stunning. The rooms were very comfortable and the bathroom had all you need. We also really appreciated the drinks and free salted chocolate chip cookies. They were delicious. The inn keepers were and their dogs were a highlight for us.
The breakfast was also absolutely delicious. Definitely would recommend this I"
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.
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.
Colonial charm meets Chesapeake Bay beauty in this historic waterfront town where 18th-century buildings house art galleries and boutiques. Rent kayaks to explore the Chester River or time your visit for the Downrigging Weekend Festival when tall ships transform the harbor.
Inside the building it was clean, quiet and nice. In the back parking lot, it was very dirty. The grounds surrounding the lot was littered with trash and debris. One person looked to be sleeping in his car. I did appreciate the very bright lighting in that lot. A small clean up of the back lot would make a big difference in first impressions!!
Inside the building it was clean, quiet and nice. In the back parking lot, it was very dirty. The grounds surrounding the lot was littered with trash and debris. One person looked to be sleeping in his car. I did appreciate the very bright lighting in that lot. A small clean up of the back lot would make a big difference in first impressions!!
The staff is friendly and helpful. The pool is refreshing, and I love the benches overlooking the waters and jetty from which you can view a lot of nature. There is always complimentary coffee and tea and apples available as well as filtered water. The best for me is that the property is on the Cross Island Trail so I can enjoy a walk/run or bike ride (you can rent bikes) to Terrapin Nature Park on the other side of Kent Island. It's also a short walk to a handful of great restaurants. We look...
The staff is friendly and helpful. The pool is refreshing, and I love the benches overlooking the waters and jetty from which you can view a lot of nature. There is always complimentary coffee and tea and apples available as well as filtered water. The best for me is that the property is on the Cross Island Trail so I can enjoy a walk/run or bike ride (you can rent bikes) to Terrapin Nature Park on the other side of Kent Island. It's also a short walk to a handful of great restaurants. We look...
Lovely room, comfy bed, great bathroom! Only complaint was that it was SO hot in the room and it was challenging to adjust that even after receiving instructions. Breakfast and coffee was excellent!
Lovely room, comfy bed, great bathroom! Only complaint was that it was SO hot in the room and it was challenging to adjust that even after receiving instructions. Breakfast and coffee was excellent!
Reyna
Reviewed February 15, 2025Reviewed February 15, 2025
Everything was excellent! Clean room, comfortable bed, friendly and helpful staff. We also enjoyed the pool and the on-site restaurant. Chef Dave’s cooking was delicious, we would go back for dinner even if we weren’t staying there!
Everything was excellent! Clean room, comfortable bed, friendly and helpful staff. We also enjoyed the pool and the on-site restaurant. Chef Dave’s cooking was delicious, we would go back for dinner even if we weren’t staying there!
The property was immaculate! The room we stayed (Chase suite) was gorgeous!!
The staff were so wonderful and helpful and the location was perfect. Loved everything about this property
The property was immaculate! The room we stayed (Chase suite) was gorgeous!!
The staff were so wonderful and helpful and the location was perfect. Loved everything about this property
MARA
Reviewed October 31, 2026Reviewed October 31, 2026
I stayed here for a quick overnight and did not utilize many of the amenities however, the staff was incredibly kind overall and with tips on dinner. This place is historic, which is a nice way of saying old but classic. Don’t expect a huge room, the photos portray the room accurately. Some things were a little rickety, but everything was clean. Overall I recommend this if you’re solo or a couple looking for a place as you enjoy the bay.
I stayed here for a quick overnight and did not utilize many of the amenities however, the staff was incredibly kind overall and with tips on dinner. This place is historic, which is a nice way of saying old but classic. Don’t expect a huge room, the photos portray the room accurately. Some things were a little rickety, but everything was clean. Overall I recommend this if you’re solo or a couple looking for a place as you enjoy the bay.
We like how close it is to the shopping center, but that it's in a quieter area. This was our second time there and the cleanliness of the bathroom was a little disappointing but otherwise it was good.
We like how close it is to the shopping center, but that it's in a quieter area. This was our second time there and the cleanliness of the bathroom was a little disappointing but otherwise it was good.
Stay here with two friends. The room was very clean and the beds comfortable. There is an indoor that looked nice though we did not use it. The Front desk guy on checkin was very friendly and helpful
Stay here with two friends. The room was very clean and the beds comfortable. There is an indoor that looked nice though we did not use it. The Front desk guy on checkin was very friendly and helpful
Heather
Reviewed January 18, 2025Reviewed January 18, 2025
Very nice hotel. One breakfast complaint: As with so many hotels, no sense of what tea-drinkers want. A wide selection of flavored "teas" (which are not actually teas), but no simple, normal tea, such as an English Breakfast Tea. This may seen like nit-picking, but it isn't to tea drinkers. You would never treat coffee drinkers this way.
Very nice hotel. One breakfast complaint: As with so many hotels, no sense of what tea-drinkers want. A wide selection of flavored "teas" (which are not actually teas), but no simple, normal tea, such as an English Breakfast Tea. This may seen like nit-picking, but it isn't to tea drinkers. You would never treat coffee drinkers this way.
For a budget-friendly escape in nature, look no further than our cheap cabins in Chestertown. Wake up in the morning to the sweet sound of birds chirping from one of our cozy retreats priced from $70 to $444 per night.
These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best family cabins near Chestertown?
Treat the youngsters to their best vacation yet in one of our Chestertown family cabins. Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay is a top pick. It comes with loads of amenities to make you and your gang feel right at home, including a meal delivery service and a travel crib. Or you can create some marvelous new memories together at Country Coziness - Lancaster County Private Cabin. A deck and a toaster are some of the conveniences to take advantage of here.
What are the best river cabins near Chestertown?
Spend your days kicking back near the water and your evenings listening to it trickling past at a river cabin near Chestertown. Leading our list is Cabin - - Picturesque Wooded Property With Unique Tiny House. This riverside property comes with on-site watersports and outdoor furniture. Or, spend your break at Cabin - Vintage Waterfront A Frame - Hideaway On The Bay. Along with its picturesque location, highlights here include on-site watersports and a firepit.
What are the best cabins with pools near Chestertown?
Put on your swimwear and enjoy a relaxing dip whenever the mood strikes when you select one of our cabin rentals with a pool. Country Coziness - Lancaster County Private Cabin is a favorite. A swimming pool and a patio are some of the other amenities that'll help make your stay comfortable. Or you can spend your getaway at Amazing Getaway: Enjoy Our Cozy Log Cabins On The Chesapeake Bay. As well as a lovely pool, this cabin comes with a swimming pool and a patio.
What are some great Chestertown cabins?
When you want to spend your vacation surrounded by nature but don't feel like roughing it, a cabin is a smart choice. Escape to Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay. This top pick comes with a firepit, a fireplace and more. Alternatively, experience comfort and outdoor fun at the same time at Pet - Friendly Lakeview Cabin W. A deck and a dock are among this retreat's amenities.
What are the best weekend cabin rentals in Chestertown?
Whether you're planning a mini break with your other half or your close friends, we'll help you locate the perfect weekend cabin getaway. One of our favorites? Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay. Featuring a patio and a firepit, you'll adore being close to nature here. Country Coziness - Lancaster County Private Cabin is another good place where you can hit pause on life. Enjoy a few nights at this escape which offers a swimming pool and a patio.
Can I find log cabins in Chestertown?
Begin your day with a hot coffee in your cozy log cabin and then go shore fishing and boating. Sound like your dream vacation? Head for 1850 Historic Log Cabin. Another relaxing retreat offering ample charm and comforts is Log Cabin In Townsend Delaware. Close-by activities like stand-up paddle boarding and shore fishing will add to the good times here.
What are the top things to see and do in Chestertown?
If you're looking to do some sightseeing around Chestertown, don't miss Washington College. Feeling adventurous? Pick up a car rental and find your way to attractions a little farther out, including Rolphs Wharf Marina. There's an amazing world to enjoy beyond your comfortable cabin!
Why should I book a cabin in Chestertown?
Affordability, outdoor activities, rustic charm — there's no end of good reasons to choose a Chestertown cabin. Leave behind the clamor of the concrete jungle and rise with the sound of songbirds and wildlife. There's so much adventure just around the corner too. Whether you're vacationing with family members, friends or your sweetheart, you'll discover the perfect rental cabin on Expedia.
What are the top nature cabins in Chestertown?
Our nature cabins in Chestertown come in many shapes and budgets, but there's one thing they all share — unparalleled access to the great outdoors. Cabin - - Picturesque Wooded Property With Unique Tiny House is a magnet for nature lovers. Amenities such as a spa tub and a firepit only make it more appealing. Whether you want to get your feet moving or just put them up, do it at Cabin - Vintage Waterfront A Frame - Hideaway On The Bay. Another great option, it comes with on-site watersports and a patio.