Book Hotels in Woolford, MD

Start date: Check-in selected.
To Date
End date: Check-out

Cabins, apartments, houseboats! We offer comfortable & private vacation rentals

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Filter by

Guest rating
Guest rating
Star rating
Payment type
Payment type
Property type
Property type
Neighborhood
Neighborhood
Traveler experience
Traveler experience
Popular locations
Popular locations
Meal plans available
Meal plans available
Amenities
Amenities
Accessibility
Accessibility

Top Woolford hotels

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

Woolford MD
This vacation home features an outdoor pool and a hot tub. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available ...
The home is in a stunning location, and was perfect for our family gathering over the Thanksgiving holiday. Everything you need for a relaxing, enjoyable getaway is provided in this home, and we’d absolutely stay there again!

Reviewed on Dec 1, 2025

Get rates
Opens in a new window Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
The Wildset

The Wildset

2.5 out of 5
209 N Talbot St St. Michaels MD
Fully refundableReserve now, pay when you stay
$209 nightly
The price is $230 total per night from Jan 28 to Jan 29
$230 total
Jan 28 - Jan 29
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 ...
Clean rooms, great staff, awesome restaurant on site called Ruse & right in downtown.

Reviewed on Jan 21, 2026

Opens in a new windowThe Wildset
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.
Comfortable house near Cambridge for a three day stay. Would stay again!

Reviewed on Dec 14, 2025

Get rates
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
$477 nightly
The price is $525 total per night from Feb 27 to Feb 28
$525 total
Feb 27 - Feb 28
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 ...
We had a great stay, hotel was very clean and food was great

Reviewed on Jan 3, 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
$179 nightly
The price is $197 total per night from Jan 28 to Jan 29
$197 total
Jan 28 - Jan 29
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. ...
Beautiful historic but with nice mix-in of modern hotel. Friendly, professional staff. Great location. My wife and I had a fantastic stay.

Reviewed on Jan 13, 2026

Opens in a new windowThe Tidewater 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
$211 nightly
The price is $240 total per night from Feb 2 to Feb 3
$240 total
Feb 2 - Feb 3
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 ...
I LOVED IT AS DID MY KIDS!!!!!

Reviewed on Jan 21, 2026

Opens in a new windowHyatt Regency Chesapeake Bay
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
$103 nightly
The price is $114 total per night from Jan 28 to Jan 29
$114 total
Jan 28 - Jan 29
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 ...
The location

Reviewed on Jan 19, 2026

Opens in a new windowSt Michaels Inn
Solomons Inn Resort & Marina

Solomons Inn Resort & Marina

2.5 out of 5
155 Holiday Dr. P.O. Box 1099 Solomons MD
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $126 total per night from Feb 1 to Feb 2
$126 total
Feb 1 - Feb 2
Total with taxes and fees
This hotel features an outdoor pool, an outdoor tennis court, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public ...
Everything was great just need better outlets and b8gger fridge

Reviewed on Jan 19, 2026

Opens in a new windowSolomons Inn Resort & Marina
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
$71 nightly
The price is $79 total per night from Jan 28 to Jan 29
$79 total
Jan 28 - Jan 29
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 ...
The room was nice

Reviewed on Dec 31, 2025

Opens in a new windowDays Inn & Suites by Wyndham Cambridge
Don't see what you're looking for?
See all available properties in Woolford
View all properties
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 $79. 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 517 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

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

5 out of 5
Posted 5 days ago
Travelocity Verified Review
"I LOVED IT AS DID MY KIDS!!!!! "
A verified traveler stayed at Hyatt Regency Chesapeake Bay
Hyatt Regency Chesapeake Bay

Explore More Ways to Travel with Travelocity