Book 5 Star Hotels in Chestertown

Name: Pendry Baltimore
Price range: $459 total

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Aug 28 - Aug 29

Tonight

Aug 29 - Aug 30

Tomorrow night

Featured Chestertown 5 Stars Hotels

7.76 mi from city center

$124 nightly

$137 total

Aug 30 - Aug 31

Total with taxes and fees

Guests staying at The Lodge at Great Oak Landing enjoy access to a golf course, a 24-hour gym, and free WiFi in public areas. You can put free parking to good use if you drive. Other amenities at this beach lodge include a seasonal outdoor pool, coffee/tea in a common area, and laundry facilities.

Pool

Parking included

Free Cancellation

0.64 mi from city center

$107 nightly

$119 total

Sep 24 - Sep 25

Total with taxes and fees

Comfort Inn & Suites Chestertown features a gym, free WiFi in public areas, and a business center. If you drive, put free parking to good use. The 24-hour front desk has staff always at the ready. Additional amenities include a seasonal outdoor pool, coffee/tea in a common area, and a meeting room.

Pool

Breakfast included

Free Cancellation

Reserve now, pay when you stay

0.58 mi from city center

$70 nightly

$78 total

Aug 30 - Aug 31

Total with taxes and fees

Red Roof Inn & Suites Chestertown features free WiFi in public areas, coffee in a common area, and free newspapers. You can put free parking to good use if you drive. The 24-hour front desk has staff always at the ready. Additional amenities include laundry facilities, a fireplace in the lobby, and a vending machine.

Pet friendly

Parking included

Quality Inn & Suites Bel Air I-95 Exit 77A

Free Cancellation

Reserve now, pay when you stay

20.67 mi from city center

$64 nightly

$72 total

Aug 30 - Aug 31

Total with taxes and fees

Guests of Quality Inn & Suites Bel Air I-95 Exit 77A have access to free WiFi in public areas. Free parking is included with your stay. Front-desk staff are standing by 24/7 to assist with any requests.

Breakfast included

Parking included

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

Free Cancellation

Reserve now, pay when you stay

24.05 mi from city center

$70 nightly

$81 total

Sep 2 - Sep 3

Total with taxes and fees

Guests of La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh enjoy a gym, free WiFi in public areas, and a business center. Free parking is included with your stay. The 24-hour front desk has multilingual staff ready to assist with securing valuables and concierge services. Additional amenities include coffee/tea in a common area, express check-in, and express check-out.

Breakfast included

Pet friendly

Best Western Plus Hotel & Conference Center

Free Cancellation

Reserve now, pay when you stay

25.92 mi from city center

$107 nightly

$125 total

Sep 2 - Sep 3

Total with taxes and fees

Guests of Best Western Plus Hotel & Conference Center have access to an indoor pool, a gym, and free WiFi in public areas. There's free parking and a cruise ship terminal shuttle. The 24-hour front desk has multilingual staff ready to assist with concierge services, dry cleaning/laundry, and luggage storage. Additional amenities include a hot tub, meeting rooms, and a conference center.

Pool

Hot Tub

Free Cancellation

Reserve now, pay when you stay

27.98 mi from city center

$148 nightly

$169 total

Sep 27 - Sep 28

Total with taxes and fees

At Historic Inns of Annapolis, guests have access to a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is available for USD 50.00 per night, and there's also limo/town car service. The front desk has multilingual staff on hand 24/7 to help with securing valuables, luggage storage, and tours or tickets. Other amenities at this historic hotel include conference space, coffee/tea in a common area, and express check-in.

Pet friendly

Free WiFi

Annapolis Waterfront Hotel, Autograph Collection

Free Cancellation

Reserve now, pay when you stay

27.93 mi from city center

$215 nightly

$245 total

Sep 7 - Sep 8

Total with taxes and fees

Annapolis Waterfront Hotel, Autograph Collection offers a 24-hour gym, a rooftop terrace, and free WiFi in public areas. Valet parking is available for USD 39 per day. The 24-hour front desk has staff standing by to help with luggage storage, securing valuables, and concierge services. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include meeting rooms, conference space, and a 24-hour business center.

Pet friendly

Free WiFi

Free Cancellation

Reserve now, pay when you stay

28.3 mi from city center

$391 nightly

$459 total

Sep 28 - Sep 29

Total with taxes and fees

Guests of Pendry Baltimore enjoy a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is USD 65 per night if you plan to drive, or hop aboard the airport shuttle (available 24 hours) for USD 108.39 per vehicle one-way. The 24-hour front desk has staff standing by to help with securing valuables, luggage storage, and dry cleaning/laundry. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this luxury hotel include a business center, a seasonal outdoor pool, and a terrace.

Pool

Spa

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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.

Best 5 star hotels in Chestertown

Guarantee yourself a relaxing time when you book the best of the best: 5 star hotels in Chestertown. After all, treating yourself to the finer things is what vacations are about.

What are the criteria for a 5 star hotel?
5 star hotel requirements include distinctive services and amenities that surpass all others. These Chestertown hotels bring an incomparable degree of quality and attention to detail, with guest satisfaction being top priority. Your 5 star hotel should be dressed to impress, with design details like marble surfaces and hi-tech fixtures.

What amenities can I expect at a 5 star hotel?
Chestertown 5 star hotels and resorts typically offer luxury amenities such as:

Gourmet restaurant
Full-service fitness center with pool
Luxury spa
Welcome gifts upon arrival
Top-of-the-line beds and linens
Designer personal care products
Premium cable, free Wi-Fi and device docking stations

How do I find an amazing 5 star hotel?
Finding 5 star hotel deals in Chestertown with Orbitz is as easy as your stay will be. For the top-shelf vacation you deserve, we’ll help you choose the right hotel in the right place:

Search hotels by price, ranging from $72 to $459
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Choose from 1,098 5 star hotels in Chestertown!

Chestertown hotels essential information

Accommodation	1,098 hotels
Lowest Price	$72
Highest Price	$459
Popular hotels	The Lodge at Great Oak Landing, Comfort Inn & Suites Chestertown, Red Roof Inn & Suites Chestertown, Historic Inns of Annapolis, Pendry Baltimore, Annapolis Waterfront Hotel, Autograph Collection, Best Western Plus Hotel & Conference Center, La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh, Quality Inn & Suites Bel Air I-95 Exit 77A

Recent Reviews

4/5 Good

"The location of the hotel was awesome along with our balcony view. However you should not have to pay an additional $50 per day to park your car especially since the garage up the street is Therefore the guests are getting pentalized to park at the hotel . Additionally the front desk women were rude and condescending"

A verified traveler stayed at Annapolis Waterfront Hotel, Autograph Collection

Posted 3 days ago