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
Reserve now, pay when you stay
0.64 mi from city center
$113 nightly
The price is $125 total per night
$125 total
Aug 10 - Aug 11
Total includes 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
Aug 10 - Aug 11
Total includes 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 vending machine, and a fireplace in the lobby.
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
$147 nightly
The price is $163 total per night
$163 total
Aug 5 - Aug 6
Total includes 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
Quality Inn & Suites Bel Air I-95 Exit 77A
2112a Emmorton Park Road, Edgewood, MD
Free Cancellation
Reserve now, pay when you stay
20.67 mi from city center
$59 nightly
The price is $66 total per night
$66 total
Sep 2 - Sep 3
Total includes 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
4 Philadelphia Ct, Rosedale, MD
Free Cancellation
Reserve now, pay when you stay
24.05 mi from city center
$78 nightly
The price is $90 total per night
$90 total
Aug 10 - Aug 11
Total includes 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
Historic Inns of Annapolis
58 State Circle, Annapolis, MD
Free Cancellation
Reserve now, pay when you stay
27.98 mi from city center
$143 nightly
The price is $163 total per night
$163 total
Aug 10 - Aug 11
Total includes 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, concierge services, and luggage storage. 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
27.95 mi from city center
$220 nightly
The price is $251 total per night
$251 total
Aug 10 - Aug 11
Total includes 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, luggage storage, 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
Sagamore Pendry Baltimore
1715 Thames St., Baltimore, MD
28.3 mi from city center
$395 nightly
The price is $464 total per night
$464 total
Sep 1 - Sep 2
Total includes taxes and fees
Guests of Sagamore 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
Courtyard by Marriott Baltimore Downtown/McHenry Row
1803 Porter Street, Baltimore, MD
Free Cancellation
Reserve now, pay when you stay
28.55 mi from city center
$125 nightly
The price is $147 total per night
$147 total
Aug 10 - Aug 11
Total includes taxes and fees
Guests of Courtyard by Marriott Baltimore Downtown/McHenry Row enjoy a gym, free WiFi in public areas, and meeting rooms. If you drive, put free parking to good use. The 24-hour front desk has staff standing by to help with dry cleaning/laundry and securing valuables. Additional amenities include a computer station, a free grocery shopping service, and express check-in.
Parking included
Free WiFi
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 $66 to $464
- Find the best-loved hotels through word-of-mouth advice when you check out over reviews by Orbitz travelers
- Choose from 1,078 5 star hotels in Chestertown!
Chestertown hotels essential information
Accommodation | 1,078 hotels |
|---|---|
Lowest Price | $66 |
Highest Price | $464 |
Popular hotels | Comfort Inn & Suites Chestertown, Red Roof Inn & Suites Chestertown, The Lodge at Great Oak Landing, Historic Inns of Annapolis, Sagamore Pendry Baltimore, Annapolis Waterfront Hotel, Autograph Collection, Quality Inn & Suites Bel Air I-95 Exit 77A, Courtyard by Marriott Baltimore Downtown/McHenry Row, La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh |
Recent Reviews
Red Roof Inn & Suites Chestertown
5/5 Excellent
"Great service "
A verified traveler stayed at Red Roof Inn & Suites Chestertown
Posted 2 days ago
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