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Find 4 Star Hotels in Chestertown, MD from SAR 778

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Compare Chestertown 4 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Annapolis Waterfront Hotel, Autograph Collection
Exterior

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (779)
"there is no shower cap, "
The price is SAR 778
SAR 887 total
includes taxes & fees
29 Dec - 30 Dec
Annapolis Waterfront Hotel, Autograph Collection
The Inn at Chesapeake Bay Beach Club
Front of property - evening/night

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (370)
"This was the perfect weekend getaway spot. I booked this stay for my husband’s birthday and the staff was so nice when they learned of the occasion. They even gave him a complimentary piece of pie! (Even if it’s not your birthday, try the apple pie.) We will definitely be back. "
The price is SAR 781
SAR 962 total
includes taxes & fees
13 Jan - 14 January 2025
The Inn at Chesapeake Bay Beach Club
The Annapolis Inn
Room

The Annapolis Inn

4.0 star property
9.0 out of 10, Wonderful, (4)
"The Annapolis Inn exceed every expectation! The owners are absolutely fabulous. The property is gorgeous and exceptionally appointed. Alex is a gourmet chef who left us wanting more each breakfast. Joe is a tremendous story teller and you will want to sit for hours listening and conversing. Both are wonderful and kind humans who gave us their undivided attention and complete care. This was my first experience at a bed and breakfast and I am forever spoiled. You won’t find better accommodations...
The Annapolis Inn
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Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Chestertown.
Sagamore Pendry Baltimore

Sagamore Pendry Baltimore

1715 Thames St., Baltimore, MD
The price is SAR 1,187 per night from Jan 12 to Jan 13
SAR 1,187
SAR 1,549 total
includes taxes & fees
12 Jan - 13 January 2025
9.4/10 Exceptional! (984 reviews)
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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.

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Chestertown?
To book a 4-star hotel in Chestertown that’s within your budget, take advantage of Expedia’s filters. Take a look at the availability during your getaway dates and use our pricing filter to set your limit. You can also list your results by the most wallet-friendly option first.

  • Search for the lowest price from SAR 1,187

What's the difference between 5-star and 4-star hotels in Chestertown?
Offering a friendly traveler experience and upmarket décor, 4-star hotels are a terrific option for your Chestertown trip. These types of stays generally feature lots of handy amenities that make it easy to unpack and recharge — think complimentary bathrobes, pools and gyms. Or enjoy even more lavishness at a 5-star hotel designed to spoil you with high-end perks and amenities. Concierge assistance, complimentary toiletries and world-class dining are typically included at these plush retreats.
Does Chestertown have any 4-star all-inclusive resorts?
Finding vacation bliss in Chestertown is as easy as entering your travel details and selecting our “All inclusive” filter. Stay and play where just about everything is already taken care of like your accommodations, meals and activities, or choose a standard 4-star resort in or around this top destination.