Book Hotels in Woolford, MD

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Top Woolford hotels

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

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

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 ...
"Everyone enjoyed the pool, dock, beach,screened in porch. They have two refrigerators, bike helmets, toddler toilet seat, step stool on third floor. Bring room darkening shades for anyone who likes to sleep late. Two baby gates for the stairs were wonderful. Bring sand toys and water shoes for all. ..."

Reviewed on Sep 1, 2026

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Opens in a new window Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted
The Wildset

The Wildset

2.5 out of 5
209 N Talbot St St. Michaels MD
Fully refundableReserve now, pay when you stay
$262 nightly
The price is $288 total per night from Oct 5 to Oct 6
$288 total
Oct 5 - Oct 6
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 ...
"Great boutique hotel with a wonderful restaurant (Ruse). We stayed 3 nights and didn’t use our rental car until we checked out."

Reviewed on Sep 13, 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
$722 nightly
The price is $765 total per night from Sep 14 to Sep 15
$765 total
Sep 14 - Sep 15
Total with taxes and fees
This vacation home features a garden, laundry facilities, and barbecue grills.
"Anne was super responsive and helpful! The house is spacious, comfortable, with an extremely well stocked kitchen - plan to cook! We had our very first seafood broil ever, thanks to the equipment on hand. There are plenty of kayaks and a canoe, with easy access to the water. The screened in porch ..."

Reviewed on Aug 9, 2026

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
$660 nightly
The price is $726 total per night from Oct 6 to Oct 7
$726 total
Oct 6 - Oct 7
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’s so lovely and elegant I almost don’t want to tell people it’s there. Stunning, perfect in every way."

Reviewed on Sep 8, 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
$189 nightly
The price is $208 total per night from Sep 29 to Sep 30
$208 total
Sep 29 - Sep 30
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. ...
"⭐️⭐️⭐️⭐️⭐️ Wonderful Birthday Getaway! We had a wonderful stay at The Tidewater Inn for my spouse’s birthday weekend. Our room was clean, spacious, comfortable, and perfect for a relaxing getaway. The location is one of the best parts of the property...you’re within walking distance of historic sites, ..."

Reviewed on Sep 12, 2026

Opens in a new windowThe Tidewater 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
$68 nightly
The price is $75 total per night from Sep 14 to Sep 15
$75 total
Sep 14 - Sep 15
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 ...
"Just need a lot of maintenance ! Old structure ! Not tables for a decent breakfast! In the morning no front desk staff 😖"

Reviewed on Sep 13, 2026

Opens in a new windowDays Inn & Suites by Wyndham 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
$94 nightly
The price is $103 total per night from Oct 14 to Oct 15
$103 total
Oct 14 - Oct 15
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
$294 nightly
The price is $334 total per night from Sep 29 to Sep 30
$334 total
Sep 29 - Sep 30
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
Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge

2.5 out of 5
2936 Ocean Gtwy Cambridge MD
Fully refundable
$118 nightly
The price is $131 total per night from Oct 5 to Oct 6
$131 total
Oct 5 - Oct 6
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 ...
Opens in a new windowComfort Inn & Suites 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 $75. 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 536 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 Wildset

The Wildset

5 out of 5
Posted 4 hours ago
Travelocity Verified Review
"Great boutique hotel with a wonderful restaurant (Ruse). We stayed 3 nights and didn’t use our rental car until we checked out."
A verified traveler stayed at The Wildset
The Wildset

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