Book Hotels in Woolford, MD

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Top Woolford hotels

The Wildset

The Wildset

2.5 out of 5
209 N Talbot St St. Michaels MD
Fully refundableReserve now, pay when you stay
$249 nightly
The price is $274 total per night from Jul 6 to Jul 7
$274 total
Jul 6 - Jul 7
Total with taxes and fees
A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self ...
"So happy we decided to stay here instead of the Perry in. Much more updated and relaxed. Staff was great."

Reviewed on Jun 12, 2026

Opens in a new windowThe Wildset
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln St. Michaels MD
$603 nightly
The price is $663 total per night from Jul 12 to Jul 13
$663 total
Jul 12 - Jul 13
Total with taxes and fees
This luxury hotel features a golf course, a full-service spa, and a marina. Families will appreciate complimentary bicycles, kid-friendly dining, and in-room ...
"It was a wonderful stay. The rooms were clean, the staff helpful and the food marvelous. I intend to visit again!"

Reviewed on Jun 8, 2026

Opens in a new windowInn at Perry Cabin
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford MD
This vacation home features a garden, laundry facilities, and barbecue grills.
"Really comfortable house, plenty of space. Lovely surroundings for a low-key quiet getaway. *Note, the nearby general store has closed permanently as of 30Apr2026"

Reviewed on May 19, 2026

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Opens in a new windowThe Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd Cambridge MD
Fully refundableReserve now, pay when you stay
$334 nightly
The price is $379 total per night from Jun 17 to Jun 18
$379 total
Jun 17 - Jun 18
Total with taxes and fees
This smoke-free resort features a private beach, a golf course, and a full-service spa. Bring the family and enjoy the children's club, mini golf, and children's ...
"The hotel was very nice enjoyed my stay."

Reviewed on Jun 8, 2026

Opens in a new windowHyatt Regency Chesapeake Bay
The Tidewater Inn

The Tidewater Inn

3 out of 5
101 E Dover St Easton MD
Fully refundableReserve now, pay when you stay
$179 nightly
The price is $197 total per night from Jun 15 to Jun 16
$197 total
Jun 15 - Jun 16
Total with taxes and fees
This traditional hotel features a full-service spa and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. ...
"Loved everything about this beautiful hotel."

Reviewed on Jun 9, 2026

Opens in a new windowThe Tidewater Inn
Hilton Garden Inn Solomons

Hilton Garden Inn Solomons

3 out of 5
13100 Dowell Road Solomons MD
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $136 total per night from Jun 25 to Jun 26
$136 total
Jun 25 - Jun 26
Total with taxes and fees
This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public ...
"24 hour gym appreciated! Nice outdoor pool- wasn’t open yet."

Reviewed on Jun 4, 2026

Opens in a new windowHilton Garden Inn Solomons
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street St. Michaels MD
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $121 total per night from Jul 7 to Jul 8
$121 total
Jul 7 - Jul 8
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of ...
"Clean old-fashioned hotel. Breakfast on weekdays was cold cereal & toast--apparently the weekends are much better. Good bed & everything worked."

Reviewed on Jun 10, 2026

Opens in a new windowSt Michaels Inn
Quality Inn

Quality Inn

2.5 out of 5
8523 Ocean Gtwy Easton MD
Fully refundable
$101 nightly
The price is $111 total per night from Jul 5 to Jul 6
$111 total
Jul 5 - Jul 6
Total with taxes and fees
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 2 conference rooms, free WiFi in public areas, and express ...
"We were traveling with a large, heavy piece of medical equipment; staff were so helpful in unloading and reloading it from our car. We appreciated having a room convenient to parking. The breakfast was better than most. The room was quiet and comfortable."

Reviewed on Jun 9, 2026

Opens in a new windowQuality Inn
Days Inn & Suites by Wyndham Cambridge

Days Inn & Suites by Wyndham Cambridge

2.5 out of 5
2917 Ocean Gateway Cambridge MD
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $90 total per night from Jun 15 to Jun 16
$90 total
Jun 15 - Jun 16
Total with taxes and fees
The hotel doesn't skimp on freebies - guests receive free continental breakfast and free self parking. Traveling on business? Take advantage of the 24-hour business ...
"I booked a room for my friend and they decided to sleep in their car because there was debris on the bed linen, a random big flying around and the plumbing wasn’t working properly. I was so embarrassed for having her stay there. I wish I could get my money back!"

Reviewed on Jun 12, 2026

Opens in a new windowDays Inn & Suites by Wyndham Cambridge
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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.

Frequently asked questions

What are the top kid-friendly hotels in Woolford?
From carefully considered amenities to extra room to move, kid-friendly hotels come with features that can help turn a standard family vacation into an incredible one. These Woolford properties make getting away with youngsters a cinch: Your crew will enjoy their time at The Retreat - The Perfect Ambiance!. A playground and animal viewing activities are among the things that help make this property a sought-after option. Alternatively, spend your Woolford escape at Waterfront Getaway with Dock. Take advantage of a playground, animal viewing activities and more here.
Where can I find cheap hotels in Woolford?
At Travelocity you'll find really nice hotels in Woolford at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Woolford rather than in Woolford. We may find you even better rates, too.
How do I find the best Woolford hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Woolford then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Woolford?
The cheapest hotel in Woolford is $90. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Woolford?
There are 534 hotels in Woolford on Travelocity.
What are the best hotels in Woolford?
Woolford has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Woolford for you!
When is the best time to visit Woolford?
If you want the joy of a fun-filled trip in peak season, visit Woolford during May, June and July. If you'd prefer the peace of off-season, book a stay during quieter months, such as November, December and January.
When is the cheapest time to stay in Woolford?
Based on historic data is usually the cheapest month to visit Woolford. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Woolford?
There are multiple hotels in Woolford that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Woolford. We have plenty of kid-friendly hotels in Woolford to choose from on Travelocity!
Why book a hotel in Woolford through Travelocity?
Because we have the top hotels in Woolford! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Woolford on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Woolford hotel reviews by fellow wanderers

Days Inn & Suites by Wyndham Cambridge

Days Inn & Suites by Wyndham Cambridge

1 out of 5
Posted 7 hours ago
Travelocity Verified Review
"I booked a room for my friend and they decided to sleep in their car because there was debris on the bed linen, a random big flying around and the plumbing wasn’t working properly. I was so embarrassed for having her stay there. I wish I could get my money back!"
A verified traveler stayed at Days Inn & Suites by Wyndham Cambridge
Days Inn & Suites by Wyndham Cambridge

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