Book Hotels in Woolford, MD

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Top Woolford hotels

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

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

Woolford
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 ...
"We enjoyed our stay in Woolford. The day was filled with fishing, swimming and boating. Thank you again for sharing your property with our family."

Reviewed on Aug 24, 2025

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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
$239 nightly
The price is $263 total per night from Oct 28 to Oct 29
$263 total
Oct 28 - Oct 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 ...
"Lovely property and friendly attentive staff. Appreciated the text updates with info and reminders of service options. Enjoyed the complimentary breakfast and smore option in the evenings. The ruse restaurant was also fantastic, had dinner there our first evening and thoroughly enjoyed it. The unique ..."

Reviewed on Oct 12, 2025

Opens in a new windowThe Wildset
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
$445 nightly
The price is $489 total per night from Nov 17 to Nov 18
$489 total
Nov 17 - Nov 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 ...
"Staff is outstanding in every aspect. Add upgrades to rooms in furniture and painting, add sugar free syrup and pancakes for breakfast. Tours and Toast were lovely."

Reviewed on Oct 17, 2025

Opens in a new windowInn at Perry Cabin
The Tidewater Inn

The Tidewater Inn

3 out of 5
101 E Dover St, Easton, MD
$179 nightly
The price is $197 total per night from Nov 2 to Nov 3
$197 total
Nov 2 - Nov 3
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. ...
"Nice hotel. Food in the restaurant was excellent"

Reviewed on Oct 15, 2025

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
$184 nightly
The price is $209 total per night from Oct 29 to Oct 30
$209 total
Oct 29 - Oct 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 ...
"Very professionally cleaned. Safe."

Reviewed on Oct 15, 2025

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 refundable
$92 nightly
The price is $102 total per night from Oct 29 to Oct 30
$102 total
Oct 29 - Oct 30
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 ...
"Price was far below others in the area. Accommodations were clean, bed was fine, it met my needs."

Reviewed on Oct 13, 2025

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
$125 nightly
The price is $139 total per night from Oct 29 to Oct 30
$139 total
Oct 29 - Oct 30
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 ...
"Breakfast choices very nice. Room clean, comfy, beautiful view. Staff very pleasant"

Reviewed on Oct 18, 2025

Opens in a new windowSolomons Inn Resort & Marina
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 Oct 29 to Oct 30
$94 total
Oct 29 - Oct 30
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 ...
"Everything was clean; staff friendly; breakfast great"

Reviewed on Oct 14, 2025

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, Rt.50 East, Cambridge, MD
Fully refundableReserve now, pay when you stay
$72 nightly
The price is $80 total per night from Oct 23 to Oct 24
$80 total
Oct 23 - Oct 24
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 ...
"Everything was clean. Well-designed interior. Good security and lighting. Ample parking. Nice breakfast."

Reviewed on Sep 28, 2025

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 $80. 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 530 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

Solomons Inn Resort & Marina

Solomons Inn Resort & Marina

5 out of 5
Posted 4 days ago
Travelocity Verified Review
"Breakfast choices very nice. Room clean, comfy, beautiful view. Staff very pleasant "
A verified traveler stayed at Solomons Inn Resort & Marina
Solomons Inn Resort & Marina

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