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
$279 nightly
The price is $307 total per night from Jul 22 to Jul 23
$307 total
Jul 22 - Jul 23
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 ...
"Perfect location, pretty room and property. Staff were very helpful and friendly!"

Reviewed on Jun 17, 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
$621 nightly
The price is $683 total per night from Jul 23 to Jul 24
$683 total
Jul 23 - Jul 24
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
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd Cambridge MD
Fully refundableReserve now, pay when you stay
$292 nightly
The price is $331 total per night from Jun 28 to Jun 29
$331 total
Jun 28 - Jun 29
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 resort is beautiful and there are plenty of amenities! The staff was very courteous and helpful. Our room was clean and I felt very comfortable. My only recommendation is for Ironman Eagleman race. Please have more and bigger shuttles running so participants and family can get to race on time. ..."

Reviewed on Jun 20, 2026

Opens in a new windowHyatt Regency Chesapeake Bay
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 28 to Jun 29
$136 total
Jun 28 - Jun 29
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 ...
"A very enjoyable stay.. A nice prorty."

Reviewed on Jun 14, 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
$102 nightly
The price is $113 total per night from Jul 7 to Jul 8
$113 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 ...
"Did like convenience to Easter Shore shops and events and other islands. However, there was no view whatsoever but a dark outdoor hall, the toilet was built for a child, and the shower was tepid at best."

Reviewed on Jun 21, 2026

Opens in a new windowSt Michaels Inn
Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge

2.5 out of 5
2936 Ocean Gtwy Cambridge MD
Fully refundable
$122 nightly
The price is $136 total per night from Jul 13 to Jul 14
$136 total
Jul 13 - Jul 14
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will ...
"My stay here was the best as usual. I come here every year when my job has a conference and I like this hotel better than the host hotel. Staff is always friendly, professional and informative"

Reviewed on Jun 10, 2026

Opens in a new windowComfort Inn & Suites Cambridge
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 24 to Jun 25
$90 total
Jun 24 - Jun 25
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 ...
"Our room and bathroom were perfectly clean, and the bed was comfortable. The pool was closed and the breakfast was wanting. Staff was responsive."

Reviewed on Jun 21, 2026

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

Cambridge Inn

2 out of 5
2831 Ocean Gateway Cambridge MD
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $83 total per night from Jun 23 to Jun 24
$83 total
Jun 23 - Jun 24
Total with taxes and fees
A restaurant, free self parking, and express check-out are among this hotel's amenities. WiFi in public areas is free. Laundry facilities are provided for your ...
"Its good just choose non smoking 🚭"

Reviewed on Jun 16, 2026

Opens in a new windowCambridge Inn
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.
Get rates
Opens in a new windowThe Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
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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 $83. 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 537 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

The Tidewater Inn

The Tidewater Inn

5 out of 5
Posted 2 days ago
Travelocity Verified Review
"Gorgeous well appointed hotel. Perfect location and tons to explore while in the area. Highly recommended"
A verified traveler stayed at The Tidewater Inn
The Tidewater Inn

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