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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

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Opens in a new window Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
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 8 to Mar 9
$408 total
Mar 8 - Mar 9
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 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.
The accommodations were perfect. Lot's of room for everyone..it was very clean,kitchen was really stocked nicely with pots ,pans,utensils,coffee pots and all of the appliances were in good working order..the view was nice of the water,swing set and fire pit..weather didn't cooperate but really enjoyed ...

Reviewed on Feb 17, 2026

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Opens in a new windowThe Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
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 15 to Mar 16
$259 total
Mar 15 - Mar 16
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 spa was relaxing, my room was clean and roomy.

Reviewed on Mar 2, 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
$179 nightly
The price is $197 total per night from Mar 8 to Mar 9
$197 total
Mar 8 - Mar 9
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 staff. Comfortable space. Great food in Tavern.

Reviewed on Feb 18, 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
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $111 total per night from Apr 1 to Apr 2
$111 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
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $105 total per night from Mar 15 to Mar 16
$105 total
Mar 15 - Mar 16
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 ...
Although the staff at the front desk was nice and courteous and the room was in a good condition, it not very clean. Dirty Spots on the bedding and bad smell in the room.

Reviewed on Mar 2, 2026

Opens in a new windowSt Michaels Inn
Quality Inn

Quality Inn

2.5 out of 5
8523 Ocean Gtwy Easton MD
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $94 total per night from Mar 15 to Mar 16
$94 total
Mar 15 - Mar 16
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 ...
Friendly helpful staff

Reviewed on Mar 6, 2026

Opens in a new windowQuality 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 9 to Mar 10
$79 total
Mar 9 - Mar 10
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 522 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

5 out of 5
Posted 13 hours ago
Travelocity Verified Review
"Friendly helpful staff"
A verified traveler stayed at Quality Inn
Quality Inn

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