Find 4 Star Hotels in Chestertown, MD from $226

  • Upfront pricing

    Our total price for your stay includes taxes and fees
  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Our top choices for Chestertown 4-star hotels

1. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (512 reviews)
"Great property super friendly, helpful staff."
United States
scott
$204 nightly
The price is $226
Dec 9 - Dec 10
Total with taxes and fees
The Inn at Chesapeake Bay Beach Club

2. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (1,000 reviews)
"Staff was Great, Great Location. Nice Restaurant Bartender was great!"
United States
Donna
$215 nightly
The price is $245
Nov 23 - Nov 24
Total with taxes and fees
Annapolis Waterfront Hotel, Autograph Collection

3. Hudson house

Hudson house
4.0 star property
Canton
7.6 out of 10, Good, (5 reviews)
"The condo was really nice and clean"
United States
Thelma
Hudson house

4. Rooftop Patio w/ View: Baltimore Retreat

Rooftop Patio w/ View: Baltimore Retreat
4.0 star property
Canton
Rooftop Patio w/ View: Baltimore Retreat

Find out more about Chestertown

Chestertown Four Star Hotel Information

When you need to book a room with luxurious amazing amenities and the best rates, the 4 star hotels in Chestertown, Maryland are incredible options. Known for their extra perks, first-rate service, and fantastic locations, each of the Chestertown 4 star hotels offers the ultimate experience for globe-trotting travelers. Relax in your expertly designed room. Kick back with around-the-clock room service.

Get a good night’s sleep with the ultra-plush bedding, and freshen up in the morning with designer-inspired body products. It’s all available when you stay at one of the top book a four star hotels in Chestertown. What’s more, thanks to Expedia you might even score a cheap great deal on a 4 star hotel in Chestertown, Maryland, areas near the hottest attractions, so you can plan a sightseeing adventure and take advantage of unbeatable discounts in one fell swoop.

Whether you’re putting together a serene getaway or want to revel in the most vibrant entertainment district, 4 star Chestertown hotels offer everything your heart desires.

Frequently Asked Questions

How much does it cost to stay in a 4-star hotel in Chestertown?

With Expedia's handy filter tool, landing a terrific deal on a 4-star hotel in Chestertown just got easier. Start by entering your chosen arrival date and length of your getaway. Then list the results by price and choose a property that best matches your budget and style.

  • Search for the lowest price from $226

What's the difference between 5-star and 4-star hotels in Chestertown?

If you decide to vacation at a 4-star hotel in Chestertown, you'll typically find loads of conveniences to make sure you're comfortable, such as a restaurant, pool and gym. You can look forward to excellent service and upscale surroundings. Opt for a 5-star hotel and you'll have access to a few more bells and whistles — think on-site spas, around-the-clock concierge and opulent turndown services. You'll most likely get extra amenities and premium services at a 5-star stay, but both are fabulous options for luxury guests.

Does Chestertown have any 4-star all-inclusive resorts?

Finding your dream hotel in Chestertown is as easy as typing in your travel details and clicking on our "All inclusive" filter. Stay and play where almost everything is already taken care of like your accommodations, meals and activities, or go for a standard 4-star resort in or around this top destination.

Are there any 4-star casino hotels in Chestertown?

To find your perfect getaway in Chestertown, use our handy filter tool to refine your search. Offering resort-style amenities and an upmarket level of service, our 4-star casino hotels are a safe bet for a good time.

Explore a world of travel with Expedia