Woolford Holiday Rentals

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Check prices for these dates

Tonight
13 Dec - 14 Dec
Tomorrow
14 Dec - 15 Dec
Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec

Our top choices for Woolford holiday rentals

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The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Holiday Home in Woolford

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
9.6 out of 10, Exceptional, (21)
"This property is beautiful and perfect for large groups. There is plenty of room and very inviting. We had a great time!"
United States
Shannon T.
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Outdoor pool, a heated pool
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

Holiday Home in Woolford

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
9.8 out of 10, Exceptional, (75)
"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."
United States
Linda S.
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Sun-loungers, beach towels
Soul Oasis - home on the Chesapeake Bay

Cottage in Lusby

Soul Oasis - home on the Chesapeake Bay
9.8 out of 10, Exceptional, (38)
"Great stay. Teresa was very helpful, the house is fun, and the location is great - nice place to visit."
United States
Samuel W.
The price is HK$973
HK$2,186 total
includes taxes & fees
16 Dec - 17 Dec
Soul Oasis - home on the Chesapeake Bay
Terrace/patio
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Holiday Home in Cambridge

Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28
10.0 out of 10, Exceptional, (80)
"Great for 10 adults and 4 grandchildren!"
United States
Phil S.
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28
Exterior detail
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cottage in Cambridge

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
10.0 out of 10, Exceptional, (16)
"Well equipped and super clean; great place!"
United States
Steve S.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Property grounds
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Cottage in Fishing Creek

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.
10.0 out of 10, Exceptional, (51)
"Nice "
United States
Henry
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.
Property grounds
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Cottage in Downtown St. Michaels

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (125)
"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!!"
United States
Meghan K.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Outdoor pool
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

Holiday Home in Cambridge

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
9.8 out of 10, Exceptional, (7)
"Wow! What an incredible property and house. We were a group of families with small kids, and it was heaven for them playing in the pool, on the dock, on the playground, and in the expansive yard. Lots of beautiful sunsets on the patio for the grown-ups too. We never had to leave. Can't recommend highly enough. "
United States
Lea F.
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
Interior
Beautiful Waterfront Retreat in Cambridge!

Holiday Home in Cambridge

Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (50)
"Beautiful place! Loved all the activities, will return in the future! Our family and friends had a blast! Thank you so much!!"
United States
Karen L.
The price is HK$1,261
HK$2,904 total
includes taxes & fees
18 Dec - 19 Dec
Beautiful Waterfront Retreat in Cambridge!
Dining
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Cabin in Port Republic

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
10.0 out of 10, Exceptional, (181)
"We thoroughly enjoyed our stay in this kitschy, cool, rustic cabin with a million-dollar view. Communing with the ospreys, hummingbirds and the bald eagle who perched numerous times on a nearby tree was an added bonus. And, the owner may be the most friendly/helpful we’ve ever rented from. We hope to be back some day. Thanks!"
United States
Brennan H.
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Exterior
Family and Pet-Friendly, Waterfront with Pier

Cottage in Cambridge

Family and Pet-Friendly, Waterfront with Pier
10.0 out of 10, Exceptional, (265)
"The property, house and amenities were exactly as described. Absolutely gorgeous views second only to the hospitality extended by Rob and Clarissa!"
United States
Tom K.
Family and Pet-Friendly, Waterfront with Pier
Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Holiday Home in Downtown St. Michaels

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (45)
"Perfect location, everything as advertised. Highly recommend "
United States
Glen H.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Exterior
Modern Flat in the Heart of St. Michaels – Walk Everywhere

Apartment in Downtown St. Michaels

Modern Flat in the Heart of St. Michaels – Walk Everywhere
9.8 out of 10, Exceptional, (57)
"Such a beautiful space in a perfect location! We were able to walk to everything — shops, restaurants, farmers market, waterfront, etc! Highly recommend!"
United States
Paige R.
Modern Flat in the Heart of St. Michaels – Walk Everywhere
Exterior
250 ACRE ESTATE ON CHESAPEAKE BAY, SLEEPS 40 W-AC VACATIONS, WEDDINGS] REUNIONS!

Holiday Home in Church Creek

250 ACRE ESTATE ON CHESAPEAKE BAY, SLEEPS 40 W-AC VACATIONS, WEDDINGS] REUNIONS!
250 ACRE ESTATE ON CHESAPEAKE BAY, SLEEPS 40 W-AC VACATIONS, WEDDINGS] REUNIONS!
Marina
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Cottage in Downtown St. Michaels

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (126)
"Prime location! "
United States
Cindy V.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Dining
Short drive to Downtown Cambridge | Private Dock | Pool | 16.5 Acres | Guest Hou

Holiday Home in Cambridge

Short drive to Downtown Cambridge | Private Dock | Pool | 16.5 Acres | Guest Hou
9.2 out of 10, Wonderful, (5)
"Great stay"
United States
Jovan J.
Short drive to Downtown Cambridge | Private Dock | Pool | 16.5 Acres | Guest Hou
Property grounds
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Cottage in Downtown St. Michaels

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, (147)
"This is such a great house - perfect location. Very roomy and comfortable. The owner is super responsive as well. Highly recommend!"
United States
maggie k.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Property grounds
Mid-Century Modern Lake House – Gorgeous Fall Views, Fire pit, Sauna, 4BR

Holiday Home in Lusby

Mid-Century Modern Lake House – Gorgeous Fall Views, Fire pit, Sauna, 4BR
9.6 out of 10, Exceptional, (7)
"Nice lake front view. Spacious living room. "
United States
Kijung S.
Mid-Century Modern Lake House – Gorgeous Fall Views, Fire pit, Sauna, 4BR
Exterior
Dollhouse in Central Historic St Michaels

Holiday Home in Downtown St. Michaels

Dollhouse in Central Historic St Michaels
9.8 out of 10, Exceptional, (56)
"We highly enjoyed our stay. It was a great location and we got a lot of use out of the screened in porch. The coffee shop out back was a great visit in the morning. "
United States
Nitarah I.
Dollhouse in Central Historic St Michaels
3 bedrooms, iron/ironing board, travel cot, free WiFi
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Holiday Home in Prince Frederick

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
9.6 out of 10, Exceptional, (5)
"We had a short stay after a sporting event in DC, it was a little less than an hour away. Convenient location and a very clean house. Kitchen was well stocked. There was little communication with the owner, which was nice vs a long list of rules, but we would have liked to know any of their local specific favorite spots or more detailed check in/check out. Worked out nicely for our family. "
United States
Carrie K.
The price is HK$1,401
HK$2,796 total
includes taxes & fees
18 Dec - 19 Dec
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
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

Extended Stay America Select Suites Lexington Park Pax River

Extended Stay America Select Suites Lexington Park Pax River

10/10 Excellent
"Clean room. Staff respect the room number privacy policy."
Derwin 1-night trip
Posted 5 days ago
Extended Stay America Select Suites Lexington Park Pax River

Find out more about Woolford

Search for holiday rentals in Woolford on Expedia! You can easily find your home rentals, villas, holiday apartments in Woolford using one of the methods below:

  • View our selection of featured holiday rentals in Woolford
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  • Enter your travel dates to view the best deals on holiday rentals in Woolford while they last

Look no further and take a look at our great range of rental properties in Woolford!

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?

Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28: This holiday home rental outside Woolford is located on a river, 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 selection of games and 1 hot tub 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.