Book Hotels in Woolford, MD

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Top Woolford hotels

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.
"Lots of space for our group! Had a great sunroom where our kids all played. It was clean and we also appreciated how much was provided in the kitchen."

Reviewed on Oct 12, 2026

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

Inn at Perry Cabin

5 out of 5
308 Watkins Ln St. Michaels MD
$435 nightly
The price is $479 total per night from Dec 9 to Dec 10
$479 total
Dec 9 - Dec 10
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 ...
"Beautiful property but rooms in need of some updates. (Dirty carpets, moldy curtains). Beds very comfortable!For $1200 a night with no amenities, it was a disappointment but was a fun trip!"

Reviewed on Oct 18, 2026

Opens in a new windowInn at Perry Cabin
The Tidewater Inn

The Tidewater Inn

3 out of 5
101 E Dover St Easton MD
Fully refundableReserve now, pay when you stay
$165 nightly
The price is $181 total per night from Nov 23 to Nov 24
$181 total
Nov 23 - Nov 24
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. ...
"Best stop on the Eastern Shore!"

Reviewed on Nov 5, 2026

Opens in a new windowThe Tidewater Inn
Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge

2.5 out of 5
2936 Ocean Gtwy Cambridge MD
Fully refundable
$114 nightly
The price is $126 total per night from Nov 17 to Nov 18
$126 total
Nov 17 - Nov 18
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 ...
"The property was very clean and smelled amazing. The staff was very friendly and accommodating. Thank you"

Reviewed on Nov 10, 2026

Opens in a new windowComfort Inn & Suites Cambridge
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
$87 nightly
The price is $96 total per night from Nov 24 to Nov 25
$96 total
Nov 24 - Nov 25
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 ...
Opens in a new windowSt Michaels Inn
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd Cambridge MD
Fully refundableReserve now, pay when you stay
$169 nightly
The price is $192 total per night from Nov 23 to Nov 24
$192 total
Nov 23 - Nov 24
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 ...
Opens in a new windowHyatt Regency Chesapeake Bay
Baymont by Wyndham Easton

Baymont by Wyndham Easton

2.5 out of 5
8523 Ocean Gtwy Easton MD
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $88 total per night from Nov 19 to Nov 20
$88 total
Nov 19 - Nov 20
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 ...
Opens in a new windowBaymont by Wyndham Easton
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
$76 nightly
The price is $84 total per night from Nov 15 to Nov 16
$84 total
Nov 15 - Nov 16
Total with taxes and fees
The hotel doesn't skimp on freebies - guests receive free on-the-go breakfast and free self parking. Traveling on business? Take advantage of the 24-hour business ...
Opens in a new windowDays Inn & Suites by Wyndham Cambridge
Comfort Inn & Suites Lexington Park near Pax River

Comfort Inn & Suites Lexington Park near Pax River

2.5 out of 5
21885 Three Notch Rd Lexington Park MD
Fully refundable
$107 nightly
The price is $119 total per night from Nov 26 to Nov 27
$119 total
Nov 26 - Nov 27
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour ...
Opens in a new windowComfort Inn & Suites Lexington Park near Pax River
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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 $84. 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 523 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

Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge

5 out of 5
Posted 15 hours ago
Travelocity Verified Review
"The property was very clean and smelled amazing. The staff was very friendly and accommodating. Thank you"
A verified traveler stayed at Comfort Inn & Suites Cambridge
Comfort Inn & Suites Cambridge

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