Woolford Vacation Rentals

Vacation Rentals in Woolford

Fridge, microwave, oven, stovetop
Waterfront Getaway with Dock
10.0 out of 10, Exceptional, (25)
"We loved the proterty! House was set up with pleanty of room for 4 of us. It was clean and comfortable. Out back was very private. Would definitely stay here again. We had a blast!"
The price is $220
$265 total
includes taxes & fees
May 20 - May 21
Waterfront Getaway with Dock
Lake
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
9.8 out of 10, Exceptional, (66)
"What a beautiful property! We did a quick couples getaway and couldn’t have had a nicer weekend. The house is a beautiful, wraparound porch country home. Floorplan was really well designed and the decor was spot on. Looking forward to coming back next fall as well!"
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Smart TV, books, printers
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
10.0 out of 10, Exceptional, (5)
"We had a lovely stay at The Blue Heron. We had a retreat scheduled with friends that we had to relocate last minute due to snow in western Maryland. We stumbled upon this listing, and the home was perfect for our needs. Plenty of beds, fully stocked kitchen, several rooms and couches for those who wanted to read, others to play games, and others to watch football playoffs on tv. The best part of the house was the dining room table that could seat up to 18 (?). It was nice to be able to not have...
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Outdoor dining
The Schultz Estate
10.0 out of 10, Exceptional, (4)
"Had a great stay! Beautiful location! House was clean roomy, overall had a great time! The only thing I would say is work on the doors closing. In restrooms."
The Schultz Estate
Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (25)
"My family and I enjoyed our stay at the Carpenter Alley Cottage in Saint Michaels! The location was perfect -- walking distance from everything! Appreciated that there was a ground floor bedroom for my parents so they didn't have to climb the stairs and my daughter loved having her own bunk bed room! I did have a few questions about the cottage and the check-in process and my inquiries were all met with a prompt response. Would love to stay here again! (One note though is that it is a smaller,...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Property grounds
Waterfront Cottage in Beautiful Hoopers Island
10.0 out of 10, Exceptional, (53)
"Had a wonderful time really enjoyed the use of the dock the house was perfect had everything you could of possibly needed definitely will be back!"
Waterfront Cottage in Beautiful Hoopers Island
Smart TV, fireplace
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
10.0 out of 10, Exceptional, (28)
"The house was great and nice area!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Property grounds
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (106)
"Wonderful return visit to St Michaels. This time at a fantastic historical home in perfect location. Home was everything you could ask for and more. Park your car and walk anywhere, within a very quiet neighborhood, yet minutes from all St Michaels offers. Highly recommend this Property and host."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Fridge, microwave, oven, stovetop
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (16)
"We had a very enjoyable and relaxing stay here for Mother's Day weekend, coming in from DC. The property is in a great spot on the water and is a short ride into town. The house itself is cozy, clean, and welcoming with everything you need (including the crab house out back, which our four year old loved!) Rebecca is a thoughtful and accommodating host, too. She gave us several recommendations for food in the area and we really enjoyed her suggested restaurants in Cambridge and in Easton on the...
The price is $264
$472 total
includes taxes & fees
May 21 - May 22
Beautiful Waterfront Retreat in Cambridge!
Fridge, microwave, stovetop, dishwasher
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, (4)
"We extremely enjoyed our stay. The house was beautiful, kitchen was well equipped and the view was spectacular, especially with the Eagles that have nested on the 32 acre property. However was disappointed in the fact that the fire places were not in working conditions and rooms should have been number. We enjoy kayaking up and down the bay and taking it all in. I would definitely stay again."
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
3 bedrooms, desk, iron/ironing board, free WiFi
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
9.8 out of 10, Exceptional, (100)
"Really enjoyed our time there. Very relaxing. Comfortable home. All amenities there. Especially loved the windows..."
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
Exterior
Soul Oasis - home on the Chesapeake Bay
10.0 out of 10, Exceptional, (6)
"Pleasant relaxing time. We were pleased and impress to locate this property"
The price is $130
$285 total
includes taxes & fees
May 20 - May 21
Soul Oasis - home on the Chesapeake Bay
Property grounds
Maryland Vacation Rental w/ Private Pool & Dock
10.0 out of 10, Exceptional, (3)
"Loved the house and kids loved the pool. We also managed to catch a half dozen crabs (August trip). House is on the smaller side, but with four bedrooms everyone had privacy and just what they needed. We'll be back!"
Maryland Vacation Rental w/ Private Pool & Dock
Fridge, microwave, oven, stovetop
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
10.0 out of 10, Exceptional, (30)
"Great place to recharge for a few days as a family! Beautiful and peaceful in the fall — though my kids are ready to come back and use the pool in warmer weather!!!"
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
Property grounds
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (104)
"Really enjoyed the house and it’s location, perfect for a couples weekend!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
View from property
Waterfront House with Dock, Kayaks, & Sailboat!
9.4 out of 10, Exceptional, (23)
"The house was nice and the property is spacious. Great views from the dining room table. A little steep heading down to the dock but not terrible. Very private setting, but also only 5 mins away from pretty much anything you could need. Some nice restaurants just across the bridge in Solomons Island. Would love to return in warmer weather to take advantage of the kayaks and water."
Waterfront House with Dock, Kayaks, & Sailboat!
Beach umbrellas, beach towels
Lakefront Maryland Cabin w/ Fire Pit, Grill & Deck
9.4 out of 10, Exceptional, (8)
"Nice place and wonderful setting. Would have been perfect if there was laundry facility at the property."
Lakefront Maryland Cabin w/ Fire Pit, Grill & Deck
Property grounds
Mid-Century Modern and Marvelous on the Bay
10.0 out of 10, Exceptional, (60)
"Beautiful view!!! Lovely home!! We so thoroughly enjoyed our stay and hope that this is just one of many visits. Thank you!"
Mid-Century Modern and Marvelous on the Bay
Pool
Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock
Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock
Property grounds
St. Michaels Waterfront Home
10.0 out of 10, Exceptional, (20)
"Beautiful house, perfect for a weekend getaway with young kids. The host was very helpful!"
St. Michaels Waterfront Home
Don't see what you're looking for?
See all available properties in Woolford
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.

Woolford Vacation Rental Travel Info

Popular accommodation
Woolford private vacation homes
Known landmarks
Great Marsh Park, Choptank River Lighthouse and Long Wharf Park
International airport
Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)

Other types of properties in Woolford you may be interested in

Lake
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
9.8 out of 10, Exceptional, (66)
"What a beautiful property! We did a quick couples getaway and couldn’t have had a nicer weekend. The house is a beautiful, wraparound porch country home. Floorplan was really well designed and the decor was spot on. Looking forward to coming back next fall as well!"
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Indoor pool, 2 outdoor pools, pool umbrellas, sun loungers
Hyatt Regency Chesapeake Bay
4.0 star property
8.8 out of 10, Excellent, (1002)
"Gorgeous property. Beautiful views. Well maintained and kept clean. The bed was the best lullaby ever. I slept ever so soundly. Breakfast was bountiful and delicious. The young lady that checked us in was on the surly side and could use some professional development on friendliness and hospitality for people of all cultures. But, the gentleman from Ghana that check me out made up for what she lacked and redeemed my experience. I would definitely stay again. "
The price is $179
$245 total
includes taxes & fees
May 22 - May 23
Hyatt Regency Chesapeake Bay
Front of property
St Michaels Inn
2.5 star property
8.2 out of 10, Very Good, (1001)
"The staff was frieendly and very helpful, and the motel was very nice. The only issue I had with the stay was the high sulfur content of the water. It stank, and that's quite unpleasant."
The price is $97
$107 total
includes taxes & fees
May 20 - May 21
St Michaels Inn
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.

Everything you need to know about Woolford vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Woolford vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Woolford vacation 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 low season months. For more hustle and bustle, you may prefer to visit Woolford in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $130 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Woolford rentals

At Expedia, we put the best Woolford vacation 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 vacation.

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 vacation rental in Woolford?

Yes, we offer vacation rentals near well known sights in Woolford, or you can choose a more secluded option if you're looking for a relaxing stay.

What's the top vacation rental in Woolford?

Bay view from Calvert Cliffs, Solomons Island & State Park nearby: You might like this vacation home rental near Woolford. It is located on a lake and has a fireplace, a patio, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals will I find in Woolford?

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

What can I see and do in Woolford?

While exploring the area, visit family-friendly sights like Richardson Maritime Museum, or get outside and enjoy nature at Blackwater National Wildlife Refuge. In the larger area, you’ll find Harriet Tubman Underground Railroad National Historical Park and Harriet Tubman Museum and Educational Center.

What’s a vacation rental in Woolford like?

A vacation rental is a private property where you can stay for a couple of days or more in Woolford. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll feel just like you're at home. If you're concerned about cleanliness, a vacation rental can provide a sense of privacy away from shared hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for a family getaway.

Recent reviews of Woolford properties
Expedia verified reviews

Inn at Perry Cabin

Inn at Perry Cabin

5/5 Excellent
Great hotel staff
"Mason and Michael at the front desk were extremely helpful."
A verified traveler stayed at Inn at Perry Cabin
Posted 2 days ago
Inn at Perry Cabin