Holiday Rentals in Woolford

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Holiday Rentals in Woolford

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

9.8 out of 10, Exceptional, (74)
"We sought a large home for a special family birthday, with multiple bedrooms, roomy eating and living areas, and water access for recreation. This house met all our requirements and more. Our grandchildren, from teen to preschool, loved the multiple kayaks, the crab traps, roasting marshmallows at the fire pit, swimming in the heated pool, finding oyster shells along the shoreline. We visited Annapolis for a sail and sightseeing, even though it meant driving back over the Bay bridge, and we...
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

9.4 out of 10, Exceptional, (20)
"The house was very nice, the host was very responsive! The outside was nice, only down side lots of mosquitos but that’s expected. "
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

9.6 out of 10, Exceptional, (120)
"Always a great stay at the John Bruff house! Location is perfect, great view of the harbor and even saw a free concert in the park!!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

10.0 out of 10, Exceptional, (179)
"Cottage was just as pictured. Lots of character and charm. Host, Brett was easy to work with and very helpful!"
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.6 out of 10, Exceptional, (15)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is €340
includes taxes & fees
13 Oct - 14 Oct
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (258)
"It is a perfect spot to relax and enjoy the water. We will book again if we are back that way. "
Family and Pet-Friendly, Waterfront with Pier

Walk to Everything House

10.0 out of 10, Exceptional, (83)
"Clean and nice place to stay"
Walk to Everything House

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (187)
"Excellent accommodations. Comfortable, good location.One way you could improve is to furnish wash cloths and hand towels. "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

10.0 out of 10, Exceptional, (12)
"Really nice property. Relaxing weekend. Stayed here with my daughter for two nights. We had a great time. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Dollhouse in Central Historic St Michaels

9.6 out of 10, Exceptional, (54)
"This is a lovely historic home that is close to town. It's nicely decorated, has a screened deck out back, and makes for a comfortable stay."
Dollhouse in Central Historic St Michaels

6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

10.0 out of 10, Exceptional, (16)
"Gorgeous views and location. "
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

Bay view from Calvert Cliffs, Solomons Island & State Park nearby

10.0 out of 10, Exceptional, (55)
"Such a beautiful place to stay. Had absolutely everything you could need. Comfy beds and tons of space. Definitely recommend staying here!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby

Waterfront Solomons Apartment

9.2 out of 10, Wonderful, (12)
"Very clean, awesome location and amazing hosts!! "
The price is €221
includes taxes & fees
8 Oct - 9 Oct
Waterfront Solomons Apartment

Cozy Cottage with access to and partially obstructed views of the bay.

9.2 out of 10, Wonderful, (28)
"Property was cozy and clean. Owners left lights on for us knowing we had a late arrival. Would definitely stay again. "
Cozy Cottage with access to and partially obstructed views of the bay.

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (79)
"We had a very nice stay and enjoyed the quiet environment and the amenities of the property. Lots of great area for walking. "
Waterfront Cottage in Beautiful Hoopers Island

Waterfront Wildlife Retreat on the Patuxent River

10.0 out of 10, Exceptional, (171)
"We went here just for a little weekend getaway for my boyfriend, his brother, his brother’s girlfriend and their kids. We had the absolute best time, such a nice getaway even if it was only for 3 days. The view of the bay from the house is gorgeous and everything was perfect. I will be recommending this stay to anyone I can! "
Waterfront Wildlife Retreat on the Patuxent River

Harbor View Suite Talbot County License Number STRN-25-58

10.0 out of 10, Exceptional, (31)
"The room and location were perfect. Very clean and comfortable space to stay and right in the heart of town. "
Harbor View Suite Talbot County License Number STRN-25-58

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

9.8 out of 10, Exceptional, (7)
"Great House "
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

9.8 out of 10, Exceptional, (43)
"Wonderful home in excellent location!!"
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

10.0 out of 10, Exceptional, (26)
"Wow, what a homerun of a vacation house - it had everything we needed and more. We had the best time and hope to be back soon."
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
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.
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Top Woolford Hotel Reviews

Find out more about Woolford

Find out more about Woolford

Everything you need to know about Woolford holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Woolford holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Woolford holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Woolford holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Woolford. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Woolford holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Woolford holiday rentals we have selected for you start as low as €221 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Woolford rentals

At Expedia, we put the best Woolford holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Woolford rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Woolford holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Woolford. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Woolford?

Yes, there are holiday rentals close to the most popular sights in Woolford, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Woolford has to offer?

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock: This highly rated holiday home rental in Woolford is located on the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Woolford?

With 6 Expedia holiday rentals, you're guaranteed to find just the right place for your Woolford stay.

What can I see and do in Woolford?

Blackwater National Wildlife Refuge and Woods Island are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Harriet Tubman Underground Railroad National Historical Park and Harriet Tubman Museum and Educational Center.

What’s a holiday rental in Woolford like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Woolford. Holiday rentals provide amenities such as hot tubs, fire pits and patios so your stay will be comfortable. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from shared hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a small group gathering.