Book 5 Star Hotels in Chestertown
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Featured Chestertown 5 Stars Hotels
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
Free Cancellation
0.64 mi from city center
$106 nightly
The price is $118 total per night
$118 total
Jun 21 - Jun 22
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
Red Roof Inn & Suites Chestertown
160 Scheeler Rd Chestertown MD
Free Cancellation
Reserve now, pay when you stay
0.58 mi from city center
$72 nightly
The price is $80 total per night
$80 total
Jun 4 - Jun 5
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 TV in a common area, and a vending machine.
Pet friendly
Parking included
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd Chestertown MD
Free Cancellation
7.76 mi from city center
$145 nightly
The price is $161 total per night
$161 total
Jun 9 - Jun 10
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
Hilton Garden Inn Baltimore/White Marsh
5015 Campbell Boulevard Baltimore MD
Free Cancellation
Reserve now, pay when you stay
23.36 mi from city center
$102 nightly
The price is $117 total per night
$117 total
Jun 7 - Jun 8
Total with taxes and fees
At Hilton Garden Inn Baltimore/White Marsh, guests enjoy features like an indoor pool, a 24-hour gym, and free WiFi in public areas. If you drive, put free parking to good use. The front desk has multilingual staff standing by 24 hours a day to assist with securing valuables and dry cleaning/laundry. Other amenities at this family-friendly hotel include meeting rooms, a conference center, and a 24-hour business center.
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
4 Philadelphia Ct Rosedale MD
Free Cancellation
Reserve now, pay when you stay
24.05 mi from city center
$78 nightly
The price is $91 total per night
$91 total
Jun 14 - Jun 15
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 concierge services and securing valuables. Additional amenities include coffee/tea in a common area, express check-in, and express check-out.
Breakfast included
Pet friendly
Hampton Inn Baltimore/Glen Burnie
6617 Ritchie Hwy Glen Burnie MD
Free Cancellation
Reserve now, pay when you stay
29.11 mi from city center
$93 nightly
The price is $107 total per night
$107 total
Jun 21 - Jun 22
Total with taxes and fees
Guests of Hampton Inn Baltimore/Glen Burnie enjoy access to free WiFi in public areas, conference space, and a 24-hour business center. If you plan to drive, free parking is available. Multilingual staff at the front desk are standing by 24/7 to help with securing valuables, dry cleaning/laundry, and luggage storage. Additional amenities include coffee/tea in a common area, express check-out, and a TV in a common area.
Breakfast included
Pet friendly
Historic Inns of Annapolis
58 State Circle Annapolis MD
Free Cancellation
Reserve now, pay when you stay
27.98 mi from city center
$165 nightly
The price is $188 total per night
$188 total
Jun 8 - Jun 9
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 luggage storage, concierge services, and securing valuables. 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
80 Compromise St Annapolis MD
Free Cancellation
Reserve now, pay when you stay
27.93 mi from city center
$220 nightly
The price is $251 total per night
$251 total
Jun 7 - Jun 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 dry cleaning/laundry, securing valuables, and luggage storage. 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
Pendry Baltimore
1715 Thames St. Baltimore MD
Free Cancellation
Reserve now, pay when you stay
28.3 mi from city center
$359 nightly
The price is $422 total per night
$422 total
Jun 21 - Jun 22
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 dry cleaning/laundry, securing valuables, and luggage storage. 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
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 $80 to $422
- Find the best-loved hotels through word-of-mouth advice when you check out over reviews by Orbitz travelers
- Choose from 1,093 5 star hotels in Chestertown!
Chestertown hotels essential information
Accommodation | 1,093 hotels |
|---|---|
Lowest Price | $80 |
Highest Price | $422 |
Popular hotels | Comfort Inn & Suites Chestertown, Red Roof Inn & Suites Chestertown, The Lodge at Great Oak Landing, Historic Inns of Annapolis, Hampton Inn Baltimore/Glen Burnie, Annapolis Waterfront Hotel, Autograph Collection, Pendry Baltimore, Hilton Garden Inn Baltimore/White Marsh, La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh |
Recent Reviews
Red Roof Inn & Suites Chestertown
1/5 Terrible
"The staff at the front is very rude. Everytime I would go to the front I would have to say hello multiple times for somebody to come to the front to assist me. There was a guy on night shift with black glasses, would always say Jesus Christ or would mumble under his breath because it seemed like I was bothering him. The tv wasn’t working another night so I went to the front, and the lady told me it is what it is. This place is very unprofessional. The towels and washcloths were still dirty looking. Will not be back."
A verified traveler stayed at Red Roof Inn & Suites Chestertown
Posted 3 hours ago
