Book 5 Star Hotels in Woolford
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Featured Woolford 5 Stars Hotels
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Woolford MD
0.39 mi from city center
Guests staying at this vacation home have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Woolford MD
2.78 mi from city center
At this vacation home, guests have access to an outdoor pool, a sauna, and a hot tub. Staff members can answer questions about accommodations, and also provide concierge services. Other amenities at this beach vacation home include an arcade/game room, laundry facilities, and local meal delivery service.
Pool
Hot Tub
Hyatt Regency Chesapeake Bay
100 Heron Blvd Cambridge MD
Free Cancellation
Reserve now, pay when you stay
8.35 mi from city center
$197 nightly
The price is $224 total per night
$224 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
Hyatt Regency Chesapeake Bay features a private beach, a golf course, and a marina. A stay here includes free parking. Multilingual staff at the front desk are standing by 24/7 to help with luggage storage, tours or tickets, 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 beach resort include a full-service spa, 2 outdoor pools, and an indoor pool.
On private beach
Pool
Comfort Inn & Suites Cambridge
2936 Ocean Gtwy Cambridge MD
Free Cancellation
Reserve now, pay when you stay
8.63 mi from city center
$105 nightly
The price is $117 total per night
$117 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
Guests of Comfort Inn & Suites Cambridge have access to an indoor pool, a 24-hour gym, and free WiFi in public areas. If you decide to drive, there's free parking. The front desk is staffed 24/7 to help with luggage storage, and answer any questions about the accommodations. Additional amenities include meeting rooms, a business center, and a computer station.
Pool
Breakfast included
St Michaels Inn
1228 S Talbot Street St. Michaels MD
Free Cancellation
18.44 mi from city center
$93 nightly
The price is $103 total per night
$103 total
Jan 11 - Jan 12, 2026
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
Solomons Inn Resort & Marina
155 Holiday Dr. P.O. Box 1099 Solomons MD
Free Cancellation
Reserve now, pay when you stay
19 mi from city center
$119 nightly
The price is $132 total per night
$132 total
Dec 30 - Dec 31
Total with taxes and fees
Guests of Solomons Inn Resort & Marina have access to an outdoor pool, a gym, and a sauna. There's free parking and an airport shuttle. The front desk has multilingual staff on hand 24/7 to help with concierge services, securing valuables, and dry cleaning/laundry. Additional amenities include free WiFi in public areas, an outdoor tennis court, and meeting rooms.
Pool
Breakfast included
The Wildset
209 N Talbot St St. Michaels MD
Free Cancellation
Reserve now, pay when you stay
19.82 mi from city center
$209 nightly
The price is $230 total per night
$230 total
Dec 28 - Dec 29
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
308 Watkins Ln St. Michaels MD
20.02 mi from city center
$574 nightly
The price is $632 total per night
$632 total
Dec 30 - Dec 31
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 securing valuables, concierge services, 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 an outdoor pool, a gym, and a sauna.
Pool
Hot Tub
The Tidewater Inn
101 E Dover St Easton MD
Free Cancellation
Reserve now, pay when you stay
19.67 mi from city center
$179 nightly
The price is $197 total per night
$197 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
Guests of The Tidewater Inn enjoy features like a full-service spa, free WiFi in public areas, and meeting rooms. If you drive, take advantage of free parking. Front-desk staff can answer questions 24/7, and assist with securing valuables, luggage storage, and concierge services. Other amenities at this spa hotel include a conference center, a business center, and coffee/tea in a common area.
Spa
Parking included
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 Woolford
Guarantee yourself a relaxing time when you book the best of the best: 5 star hotels in Woolford. 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 Woolford 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?
Woolford 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 Woolford 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 $103 to $632
- Find the best-loved hotels through word-of-mouth advice when you check out over reviews by Orbitz travelers
- Choose from 515 5 star hotels in Woolford!
Woolford hotels essential information
Accommodation | 515 hotels |
|---|---|
Lowest Price | $103 |
Highest Price | $632 |
Popular hotels | The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks, Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock, Hyatt Regency Chesapeake Bay, Inn at Perry Cabin, Solomons Inn Resort & Marina, The Tidewater Inn, St Michaels Inn, Comfort Inn & Suites Cambridge, The Wildset |
Recent Reviews
Solomons Inn Resort & Marina
5/5 Excellent
"The staff was very friendly and helpful checking in and out. They were able to answer any questions I had and provided wonderful feedback. They property is very convenient to some shops and a short walk to the island. "
A verified traveler stayed at Solomons Inn Resort & Marina
Posted 12 days ago
