Book 5 Star Hotels in Chestertown
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Featured Chestertown 5 Stars Hotels
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
Oct 19 - Oct 20
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 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
$124 nightly
The price is $137 total per night
$137 total
Oct 14 - Oct 15
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
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
Free Cancellation
0.64 mi from city center
$98 nightly
The price is $108 total per night
$108 total
Nov 8 - Nov 9
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
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
2112b Emmorton Park Rd Edgewood MD
Free Cancellation
Reserve now, pay when you stay
20.67 mi from city center
$79 nightly
The price is $88 total per night
$88 total
Nov 2 - Nov 3
Total with taxes and fees
At La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A, guests have access to free WiFi in public areas, coffee in a common area, and laundry facilities. If you drive, put free parking to good use. The 24-hour front desk has staff always at the ready.
Breakfast included
Pet friendly
Hampton Inn Baltimore/White Marsh
8225 Town Center Drive Baltimore MD
Free Cancellation
Reserve now, pay when you stay
23.47 mi from city center
$102 nightly
The price is $117 total per night
$117 total
Oct 20 - Oct 21
Total with taxes and fees
Renovated in 2023, Hampton Inn Baltimore/White Marsh offers a gym, free WiFi in public areas, and a seasonal outdoor pool. Self parking is available for USD 4.10 per day. The 24-hour front desk has staff standing by to help with securing valuables and luggage storage. Additional amenities include coffee/tea in a common area, express check-in, and express check-out.
Pool
Breakfast 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
$70 nightly
The price is $81 total per night
$81 total
Oct 18 - Oct 19
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
5625 O'Donnell Street Baltimore MD
Free Cancellation
Reserve now, pay when you stay
25.92 mi from city center
$115 nightly
The price is $130 total per night
$130 total
Oct 18 - Oct 19
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 dry cleaning/laundry, tours or tickets, and luggage storage. Additional amenities include a hot tub, meeting rooms, and a conference center.
Pool
Hot Tub
Historic Inns of Annapolis
58 State Circle Annapolis MD
27.98 mi from city center
$119 nightly
The price is $136 total per night
$136 total
Nov 11 - Nov 12
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 concierge services, securing valuables, 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
Pendry Baltimore
1715 Thames St. Baltimore MD
Free Cancellation
Reserve now, pay when you stay
28.3 mi from city center
$409 nightly
The price is $481 total per night
$481 total
Nov 2 - Nov 3
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 $481
- Find the best-loved hotels through word-of-mouth advice when you check out over reviews by Orbitz travelers
- Choose from 1,098 5 star hotels in Chestertown!
Chestertown hotels essential information
Accommodation | 1,098 hotels |
|---|---|
Lowest Price | $80 |
Highest Price | $481 |
Popular hotels | Red Roof Inn & Suites Chestertown, The Lodge at Great Oak Landing, Comfort Inn & Suites Chestertown, La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh, Historic Inns of Annapolis, Best Western Plus Hotel & Conference Center, Pendry Baltimore, Hampton Inn Baltimore/White Marsh, La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A |
Recent Reviews
Historic Inns of Annapolis
5/5 Excellent
"We stayed here overnight so that we didn't have to travel from MoCo to Annapolis for an early morning conference. We stayed in the Maryland Inn, it was quaint, very clean, and cute. We really enjoyed the property, its location to the water and the conference. We'd definitely stay here again."
A verified traveler stayed at Historic Inns of Annapolis
Posted 5 hours ago
Best Western Plus Hotel & Conference Center
5/5 Excellent
"Oh my goodness thanks to all who made our stay so covenant and comfortable. I would definitely suggest a stay here if you are in the area. Kindest Regards"
A verified traveler stayed at Best Western Plus Hotel & Conference Center
Posted 6 hours ago