Find Oceanfront Hotels in Chestertown, MD from CA $457

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Check availability on Chestertown Oceanfront Hotels

Tonight
Apr 2 - Apr 3
Tomorrow
Apr 3 - Apr 4
This weekend
Apr 3 - Apr 5
Next weekend
Apr 10 - Apr 12

Our top choices for Chestertown hotels with an ocean view

Premium bedding, down comforters, pillowtop beds, in-room safe

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (914 reviews)
"Great waterfront room with roomy balcony. Gym was nice also. Can't wait for the var and restaurants to open."
United States
Douglas
The price is CA $401
CA $457 total
includes taxes & fees
Apr 12 - Apr 13
Annapolis Waterfront Hotel, Autograph Collection
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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Find out more about Chestertown

Discover top Chestertown attractions

Chestertown, Maryland, offers a charming blend of history, culture, and outdoor activities that will delight any traveller. Start your journey by exploring the historic district, where cobblestone streets are lined with beautifully preserved 18th-century buildings. The Chestertown Tea Party Festival, held annually, commemorates the town's pivotal role in the American Revolution and is a lively celebration with parades, crafts, and local cuisine. For nature enthusiasts, the nearby Sassafras Natural Resources Management Area presents a stunning backdrop for hiking and birdwatching, showcasing the region's diverse ecosystems. Art lovers will appreciate the Chestertown Arts League, which hosts a variety of exhibitions and workshops, providing an insight into local talent. Additionally, a relaxing cruise along the Chester River allows you to soak in the area’s picturesque scenery while learning about its rich maritime history. When it comes to accommodation, consider staying near the waterfront, where boutique hotels offer not only comfort but also stunning views of the river. Imagine enjoying a morning coffee while watching boats glide by, or taking a leisurely stroll along the waterfront, followed by a gourmet meal at a nearby restaurant. Chestertown seamlessly combines a quaint, community spirit with activities, making it a perfect spot for a memorable family getaway.

Find the best oceanfront hotels and resorts in Chestertown

For those seeking a picturesque getaway in Chestertown, Maryland, these hotels offer stunning ocean views and a serene atmosphere, perfect for unwinding by the water.

The Lodge at Great Oak Landing

  • Why it's great for scenic vacations: The Lodge at Great Oak Landing is an ideal retreat for travelers, an excellent guest review rating of 8.2. With breathtaking marina and water views, guests can indulge in the beauty of the Chesapeake Bay right from their accommodations. The lodge also features direct beach access, ensuring that travelers can easily enjoy sun-soaked days by the water's edge.
  • Other amenities: Guests will appreciate the array of recreational options, including a shared secured pool with sun loungers and a private sandy beach for relaxation. For active travelers, the lodge offers 24-hour fitness facilities, a golf course onsite, and beach volleyball for some friendly competition. Additional conveniences include self-parking, a mini-refrigerator in rooms, and beach umbrellas for those sunny days by the shore.
  • Nearby attractions: Kinnairds Point Drive - 19.6 km, Still Pond Station Park - 24.5 km

Top Chestertown Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

6/10 Okay
"All restaurants onsite were not open! We had to order from a restaurant nearby but it really was not set up properly for room service. We had to go there to order and pickup and they were not really sure of the process for hotel guests so we just paid with a separate CC. Breakfast was essentially not available and we had to go to town to pickup breakfast as well. The heat in our room did not work for the first day and night! The hotel knew they had a situation going on but did not say anything to us in advance and the hotel was sold-out.At first they suggested a space heater but then another supervisor came on duty and told us those were not premitted - and we could understand why. It was fixed by our second night. We were told we would get a credit toward the first night but we did not?"
Nancy 2-night trip
Posted 4 days ago
Annapolis Waterfront Hotel, Autograph Collection

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 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 Main Beach for some relaxation by the water. Experience the area's university life, and make time for local attractions like Washington College and Historical Society of Kent County Maryland. For even more to see and do, pay a visit to Rolphs Wharf Marina or Northern Chesapeake Bay.
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.

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