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Top Woolford hotels

"Endless Summer" Waterfront on the Chesapeake Bay!

"Endless Summer" Waterfront on the Chesapeake Bay!

Woolford MD
An indoor pool is featured at this vacation home, along with laundry facilities and barbecue grills.
We had a great visit at “Endless Summer “. Everything was as advertised. House, pool and property were great. Enjoyed seeing eagles on the dock in the mornings. Communication with the host was timely and helpful.

Reviewed on Dec 30, 2025

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Opens in a new window"Endless Summer" Waterfront on the Chesapeake Bay!
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 ...
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

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Opens in a new window Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted
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.
Great host. Great house.Great location.This house is the best. Stay in a lot of VRBO houses and this one is at the top of our list.

Reviewed on Feb 24, 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
$371 nightly
The price is $408 total per night from Mar 17 to Mar 18
$408 total
Mar 17 - Mar 18
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
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd Cambridge MD
Fully refundableReserve now, pay when you stay
$228 nightly
The price is $259 total per night from Mar 23 to Mar 24
$259 total
Mar 23 - Mar 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 ...
The pools were warm and relaxing

Reviewed on Mar 9, 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
$169 nightly
The price is $186 total per night from Mar 17 to Mar 18
$186 total
Mar 17 - Mar 18
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. ...
The property was beautiful and we enjoyed the room, the bar and the restaurant for breakfast. It is also in a great location in a very walkable town area.

Reviewed on Mar 12, 2026

Opens in a new windowThe Tidewater Inn
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
$107 nightly
The price is $119 total per night from Apr 1 to Apr 2
$119 total
Apr 1 - Apr 2
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 ...
There was a terrible cigarette smell. We ended having to leave in middle of night because we could no longer stand it.

Reviewed on Mar 2, 2026

Opens in a new windowComfort Inn & Suites Lexington Park near Pax River
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street St. Michaels MD
$103 nightly
The price is $114 total per night from Mar 31 to Apr 1
$114 total
Mar 31 - Apr 1
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 ...
Continental breakfast was unavailable. When asked why breakfast was not available was told due to remodeling and that we should have been told when we checked in. Should have been informed long before check in! Bed was extremely uncomfortable, well past needing to be replaced.

Reviewed on Mar 12, 2026

Opens in a new windowSt Michaels 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
$71 nightly
The price is $79 total per night from Mar 17 to Mar 18
$79 total
Mar 17 - Mar 18
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 ...
It was short and the bathroom could have been a bit cleaner.

Reviewed on Mar 2, 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 $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 516 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

Quality Inn

Quality Inn

3 out of 5
Posted 23 hours ago
Travelocity Verified Review
"The room had a old smoke smell and was very old"
A verified traveler stayed at Quality Inn
Quality Inn

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