Book 5 Star Hotels in Chesapeake Beach

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Oct 4 - Oct 5
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Featured Chesapeake Beach 5 Stars Hotels

Rod 'N' Reel Resort

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave, Chesapeake Beach, MD
Free Cancellation
Reserve now, pay when you stay
0.27 mi from city center
$169 nightly
The price is $185 total per night
$185 total
Oct 6 - Oct 7
Total with taxes and fees
Guests of Rod 'N' Reel Resort enjoy a marina, an indoor pool, and a 24-hour gym. The front desk is staffed 24/7 to help with securing valuables, tours or tickets, and luggage storage. Additional amenities include a sauna, meeting rooms, and conference space.
Pool
Spa
Quality Suites

Quality Suites

2.5 out of 5
11765 Business Park Dr, Waldorf, MD
Free Cancellation
Reserve now, pay when you stay
20.07 mi from city center
$85 nightly
The price is $94 total per night
$94 total
Oct 5 - Oct 6
Total with taxes and fees
Guests of Quality Suites enjoy a gym, free WiFi in public areas, and a meeting room. Free parking is included with your stay. The 24-hour front desk has staff standing by to help with dry cleaning or laundry, and answer any questions about the accommodations. Additional amenities include laundry facilities, a gift shop, and a vending machine.
Breakfast included
Parking included
The Wildset

The Wildset

2.5 out of 5
209 N Talbot St, St. Michaels, MD
Free Cancellation
Reserve now, pay when you stay
17.86 mi from city center
$239 nightly
The price is $263 total per night
$263 total
Oct 6 - Oct 7
Total with taxes and fees
The Wildset features free WiFi in public areas and a gift shop. If you drive, take advantage of free parking. Front-desk staff can help with concierge services, and provide local restaurant recommendations. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls.
Breakfast included
Pet friendly
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
17.92 mi from city center
$549 nightly
The price is $604 total per night
$604 total
Nov 3 - Nov 4
Total with taxes and fees
Inn at Perry Cabin features a golf course, a marina, and a full-service spa. If you drive, put free valet parking to good use. The 24-hour front desk has multilingual staff ready to assist with concierge services, luggage storage, and securing valuables. 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 an outdoor pool, a gym, and a sauna.
Pool
Hot Tub
Residence Inn by Marriott Waldorf

Residence Inn by Marriott Waldorf

3 out of 5
3020 Technology Place, Waldorf, MD
Free Cancellation
Reserve now, pay when you stay
21.12 mi from city center
$110 nightly
The price is $122 total per night
$122 total
Oct 19 - Oct 20
Total with taxes and fees
Residence Inn by Marriott Waldorf features a gym, free WiFi in public areas, and a conference center. Self parking is available for USD 12 per day. The 24-hour front desk has staff standing by to help with securing valuables and dry cleaning/laundry. Additional amenities include a 24-hour business center, a seasonal outdoor pool, and coffee/tea in a common area.
Pool
Breakfast included
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
Free Cancellation
18.34 mi from city center
$95 nightly
The price is $105 total per night
$105 total
Oct 6 - Oct 7
Total with taxes and fees
St Michaels Inn features free WiFi in public areas, a conference center, and a seasonal outdoor pool. If you decide to drive, there's free parking. Front-desk staff can help with tours or tickets, and provide local restaurant recommendations. Additional amenities include a computer station, a terrace, and laundry facilities.
Pool
Breakfast included
SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

3 out of 5
189 Admiral Cochrane Drive, Annapolis, MD
Free Cancellation
Reserve now, pay when you stay
19.27 mi from city center
$105 nightly
The price is $120 total per night
$120 total
Nov 2 - Nov 3
Total with taxes and fees
At SpringHill Suites by Marriott Annapolis, guests enjoy features like an indoor pool, a 24-hour gym, and free WiFi in public areas. Self parking is offered for USD 10.00 per day. Front-desk staff can answer questions 24/7, and assist with concierge services, luggage storage, and securing valuables. Additional amenities include a hot tub, conference space, and a 24-hour business center.
Pool
Hot Tub
Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG

2.5 out of 5
1 Womack Dr, Annapolis, MD
Free Cancellation
19.31 mi from city center
$97 nightly
The price is $111 total per night
$111 total
Oct 14 - Oct 15
Total with taxes and fees
Renovated in 2025, Candlewood Suites Annapolis by IHG offers a 24-hour gym, free WiFi in public areas, and a 24-hour business center. You can put free parking to good use if you drive. The 24-hour front desk has staff standing by to help secure valuables, and answer any questions about the accommodations. Additional amenities include coffee/tea in a common area, a computer station, and laundry facilities.
Pet friendly
Parking included
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3 out of 5
170 Admiral Cochrane Dr, Edgewater, MD
Free Cancellation
Reserve now, pay when you stay
19.33 mi from city center
$113 nightly
The price is $129 total per night
$129 total
Oct 19 - Oct 20
Total with taxes and fees
Sonesta ES Suites Annapolis features a 24-hour gym, free WiFi in public areas, and a 24-hour business center. Self parking is offered for USD 7 per night. The front desk is staffed 24/7 to help secure valuables, and answer any questions about the accommodations. Additional amenities include a seasonal outdoor pool, coffee/tea in a common area, and a meeting room.
Pool
Breakfast included
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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 Chesapeake Beach

Guarantee yourself a relaxing time when you book the best of the best: 5 star hotels in Chesapeake Beach. 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 Chesapeake Beach 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?
Chesapeake Beach 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 Chesapeake Beach 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 $94 to $604
  • Find the best-loved hotels through word-of-mouth advice when you check out over reviews by Orbitz travelers
  • Choose from 755 5 star hotels in Chesapeake Beach!

Chesapeake Beach hotels essential information

Accommodation
755 hotels
Lowest Price
$94
Highest Price
$604
Popular hotels
Rod 'N' Reel Resort, Sonesta ES Suites Annapolis, SpringHill Suites by Marriott Annapolis, St Michaels Inn, The Wildset, Candlewood Suites Annapolis by IHG, Inn at Perry Cabin, Quality Suites, Residence Inn by Marriott Waldorf

Recent Reviews

Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG

5/5 Excellent
"Clean and comfortable room."
A verified traveler stayed at Candlewood Suites Annapolis by IHG
Posted 6 days ago
Candlewood Suites Annapolis by IHG

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