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Find Oceanfront Hotels in Chestertown, MD from CA $182

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Top Chestertown Oceanfront Hotels

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Pool
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, 53 reviews
"My family of 4 stayed here. So many things to do outside-truly a good time. So many games and accessories to have an easy good time. Would definitely stay at this place again."
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Hidden gem with water and golf course views! Bike ride to downtown!
Smart TV, DVD player, table tennis, music library
Hidden gem with water and golf course views! Bike ride to downtown!
10.0 out of 10, Exceptional, 26 reviews
"Had a most relaxing time in a cute house with an ideal location. Was impressed with the cleanliness of the house and the ease with which we could locate items we needed thanks to an excellent labeling system."
Hidden gem with water and golf course views! Bike ride to downtown!
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
Property grounds
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
10.0 out of 10, Exceptional, 86 reviews
"Just returned from out two night stay at the Connor's waterfront home in Chestertown. It was FABULOUS. We were in this lovely historic town for a family wedding at Britland Manor, and were fortunate to find this charming, well appointed waterfront home. It was perfect for our family of 6 adults and a toddler, providing plenty of space both indoors and out, plus a well appointed kitchen. Unfortunately we didn't have time to use paddleboards, canoe or any of the other outdoor activities available,...
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
Harbor View Haven | Waterfront w/ HOT TUB + Dock!
Exterior
Harbor View Haven | Waterfront w/ HOT TUB + Dock!
10.0 out of 10, Exceptional, 8 reviews
"Could not recommend more highly. The house was as described, except for a prettier view that photos simply can’t do justice. The property was equipped with everything you would need to cook, work remotely, spend time on the water, or enjoy a cozy night in. Thank you so much for sharing your lovely home"
Harbor View Haven | Waterfront w/ HOT TUB + Dock!
Charming Chestertown Waterfront Cottage
Beach towels
Charming Chestertown Waterfront Cottage
10.0 out of 10, Exceptional, 59 reviews
"This is a great place to relax. The house had everything we needed and was very comfortable."
Charming Chestertown Waterfront Cottage
Quaint cottage with amazing sunset views to soak up nature
Beach
Quaint cottage with amazing sunset views to soak up nature
10.0 out of 10, Exceptional, 2 reviews
"We loved this cozy cabin. It was extremely clean and furnished with everything we needed. The beds were super comfortable, the sheets top quality and the towels were super thick. The house was just feet from the Chesapeake Bay snd Neely built wooden steps led us right down. To water’s edge. The neighborhood was very quiet. We will return for sure."
Quaint cottage with amazing sunset views to soak up nature
Private pier and pool at this waterfront Chestertown home
Aerial view
Private pier and pool at this waterfront Chestertown home
9.8 out of 10, Exceptional, 22 reviews
"We stayed at Peir Pleaseure for Washington college homecoming weekend. We had a BBQ by the pool for our son and his friends. We enjoyed the views of the Chester Riiver from the pier. The house was clean and easiliy accomodates 2 families ."
Private pier and pool at this waterfront Chestertown home
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
2 bedrooms, iron/ironing board, free WiFi, bed sheets
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
9.8 out of 10, Exceptional, 77 reviews
"We had a great stay and the property is well maintained. They had a lot of extras for our convenience such as toothbrushes, snacks, and more. The dock and view was beautiful and relaxing. We plan to come back soon!"
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
Exterior
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
9.8 out of 10, Exceptional, 19 reviews
"This is the second year we stayed there. We met with the agent to explain what we rented the home for. She agreed and we rented the property. This year, although she had my direct cell number, she left me a note on the island about everything she was disappointed in from the previous year—everything we discussed in person before renting the home. In addition, the first year, I spoke with her and shared some things that needed to be fixed in the home, and when we returned this year, none of the...
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
Langford Creek Estate | Waterfront w/ HOT TUB + Deck!
TV, fireplace
Langford Creek Estate | Waterfront w/ HOT TUB + Deck!
9.2 out of 10, Wonderful, 5 reviews
"The owners were very flexible with us and understanding when it came to a booking mistake on my end. The house is lovely and the property is absolutely gorgeous. The deck was picture perfect. Highly recommend for a getaway on the eastern shore!"
Langford Creek Estate | Waterfront w/ HOT TUB + Deck!
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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.

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Chestertown Oceanfront Hotels information

 

Oceanfront Hotels in Chestertown

21

Highest price
CA $182
Cheapest price
CA $182
Number of guest reviews
233
Total number of hotels in Chestertown
988

 

Frequently asked questions

What is Chestertown like for a seaside holiday?
Make your Chestertown getaway exceptional by staying somewhere with coastal views. Take a break from the beach and experience the university life in Chestertown.
What are some of the top hotels with ocean views in Chestertown?
Great Oak Manor is a B&B located on a private beach. It offers a private beach, spa services, a snack bar, free full breakfast, and free WiFi.
What are the highlights to see in Chestertown?
After checking into your accommodation of choice, you’ll probably want to venture out and explore. If you’re eager to check out the beaches, head to Betterton Beach or Earle Landing for some relaxation by the water. Experience the area’s university life, and make time for local attractions like Washington College and River Arts Chestertown. For even more to see and do, pay a visit to Rolphs Wharf Marina or Historical Society of Kent County Maryland.
Why should I choose an oceanview hotel for my Chestertown vacation?
Reward yourself with an oceanview hotel and enjoy great sea views during your trip to Chestertown. We make it simple to get the perfect hotel when you use the ocean view filter in the search results to narrow your search.

Recent Reviews in Chestertown
Expedia verified reviews

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

5/5 Excellent
Visit Annapolis and stay at this Hotel.
"Beautiful upscale accommodations. Within walking distance to everything you'll want to see and do. You want a view and a high level of service, then you'll pay for it. Loved the vallet setvice so quick and easy. That is the only option you have at this hotel. Downtown and Historic Annapolis are so pretty with lots of shops and eateries. Lots of taverns too if you travel with no kids. View of the Chesapeake Bay and Bridge. "
A verified traveller stayed at Annapolis Waterfront Hotel, Autograph Collection
Posted 6 days ago
Annapolis Waterfront Hotel, Autograph Collection