Are there any 5-star vacation rentals in Chestertown?

You won't find any 5-star vacation rentals in Chestertown on our site, but there are a range of other highly rated options worth checking out. Scan through our vacation rentals in Chestertown to book the best place for your getaway.

Somewhere over the rainbow... Terrific view on the plane back to the North.

Find 5 Star Hotels in Chestertown, MD from $241

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Compare Chestertown 5 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Seasonal outdoor pool, cabanas (surcharge), pool umbrellas

"A fantastic hotel. Great location, pool, services, food, and rooms. One of our best hotel stays in years."

$407 nightly

Oct 20 - Oct 21

Total with taxes and fees

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Explore similar 4-star hotels

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

Annapolis Waterfront Hotel, Autograph Collection

80 Compromise St, Annapolis, MD

$212 nightly

$241 total

Nov 2 - Nov 3

Total with taxes and fees

8.8/10 Excellent! (868 reviews)

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Pool Spa Hot tub Breakfast included Waterpark

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.

Learn more about Chestertown

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.

See all hotels in Chestertown

Top Chestertown Hotel Reviews

Sagamore Pendry Baltimore

10/10 Excellent

"Absolutely great stay"

Find out more about Chestertown

Indulge your every desire on your upcoming getaway. After all, you love the finer things in life, both at home and when you book a getaway. You'll join the multitudes of vacationers who have made Chestertown so popular in the last year. There's no reason to delay a getaway to Chestertown any longer. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Book one of Expedia's luxurious 5-star hotels in Chestertown and get ready to enjoy the getaway of a lifetime. You deserve the great vacation you're dreaming about.

5-Star Hotels in Chestertown

You can expect superior customer service from your hotel. Michelin-starred restaurants, concierges, and in-room spa sessions are all at the ready. You're sure to find exactly the accommodation you need. You'll be pleased to note that the hotels in Chestertown offer great customer service, averaging 3.8 in our ranking system, setting you up for a truly relaxing getaway. How do you want to relax? A reflexology treatment that will leave you feeling refreshed and alive? 24-hour room service, so you can order that berry tart in the wee hours of the morning? A full-body massage to help your cares fall away?

But you aren't going to spend your entire vacation in your room, of course. Don't worry. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. Whatever you plan to do, the 5-star hotels in Chestertown are the perfect place to relax after a busy day. Ready to learn more? Plenty of visitors recommend this location.

Your Getaway Starts Today

The results are in, and Chestertown 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. Expedia can help you land a great deal on accommodation. Your great getaway is just a mouse-click away. Select one of the 5-star hotels in Chestertown today and soothe yourself in the lap of luxury tomorrow.

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Chestertown?

How much you pay for a 5-star hotel in Chestertown depends on factors like when you plan to go and the length of your stay. An insider tip for bagging the best deal? Use our pricing filters to check out all of the available hotels for your preferred dates.

Search for the lowest price per night from $241

What makes a hotel 5 stars in Chestertown?

In Chestertown, a hotel must offer a certain number of upscale amenities to be rated 5 stars. These can include on-site gyms, gourmet restaurants, saunas and spas, complimentary luxury toiletries, premium bedding and more. What also sets 5-star hotels apart is their outstanding service. You'll enjoy things like in-room massages, nightly turn-down services and concierge services. Some may also offer special touches like welcome gifts.

Are there any 5-star all-inclusive resorts in Chestertown?

Our filters are the best way to narrow down what you're looking for. Select "5-star" and "All inclusive" to see the most luxurious properties in Chestertown where your meals, lodging, entertainment and activities are included in the price. At these escapes, your trip is pure leisure from the moment you put down your suitcase.

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