Search Vacation Homes in Woolford

Compare 213 Vacation Homes in Woolford with updated reviews, rates, and availability.

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, 27 reviews
"The house was perfect for our needs. It has a cute, fenced in yard so our 2 dogs could hang outside. It had everything we needed for a wonderful weekend birthday celebration!"
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Shewell's A-Frame on Mill Creek
10.0 out of 10, Exceptional, 1 review
The price is $225
$458 total
includes taxes & fees
Jun 12 - Jun 13
Shewell's A-Frame on Mill Creek
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
10.0 out of 10, Exceptional, 102 reviews
"Loved the house!"
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
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Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
10.0 out of 10, Exceptional, 4 reviews
"We were in town for a friends wedding. This was the perfect location as it was right in between the Catholic Church for the nuptial mass and the reception site. This place certainly did not disappoint. There was plenty of space for our large family, the home was well equipped and stocked with the necessary items. It was a relatively short stay, but I wish we had a bit more time and better weather to enjoy the use of kayaks - our one free morning was a bit chilly for us Florida folks, and we had...
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
The Schultz Estate
9.6 out of 10, Exceptional, 5 reviews
"This house is great for large groups with plenty of comfortable bedrooms, three bathrooms (note one is only a tub, no shower), and loads of outdoor seating and fire options. This is an old farmhouse, so quirks of an old wooden house on the Eastern shore come with that. Personal bug spray at this property is essential as the mosquitos are very intense. The owner did stop by to give us a lawn spray for them but we did not use it as I am a master naturalist and community garden manager who is...
The Schultz Estate
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, 4 reviews
"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!
Waterfront House with Dock, Kayaks, & Sailboat!
9.4 out of 10, Exceptional, 23 reviews
"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!
Stunning River Front Home - Private Dock - 90 minutes from Washington DC
9.8 out of 10, Exceptional, 14 reviews
"We booked a long weekend for our daughter’s graduation from St Mary’s. The house was beautiful and so spacious for our adult children and grandchildren to all be in one location without feeling cramped. We loved having the fire pit and room to throw a football around. Thank you for sharing your home Victoria!"
Stunning River Front Home - Private Dock - 90 minutes from Washington DC
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
9.6 out of 10, Exceptional, 24 reviews
"If you have a big group this is the place for you! We had a great time!!"
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
Shewell’s Rambler in the Chesapeake Ranch Estates
9.2 out of 10, Wonderful, 19 reviews
"Nice and super clean. Nice location. We will stay again next time we visit family. "
Shewell’s Rambler in the Chesapeake Ranch Estates
Newly Remodeled Home, 10 Minute Walk to Downtown
10.0 out of 10, Exceptional, 5 reviews
"Very clean house with comfortable beds. Enjoyed our stay!"
Newly Remodeled Home, 10 Minute Walk to Downtown
Riverside House w/ Kayaks, Piano & Fireplace
8.8 out of 10, Excellent, 10 reviews
"Clean property and just what we needed to gather with family nearby"
Riverside House w/ Kayaks, Piano & Fireplace
Grace Cottage, Saint Michaels Walk to everything!
10.0 out of 10, Exceptional, 1 review
"Beautiful house. Great location. Host was very responsive to questions. Thanks for a great stay"
Grace Cottage, Saint Michaels Walk to everything!
Hudson Creek Retreat, 5 Acre Waterfront Home, Pool, Pier, Fishing & Crabbing
Hudson Creek Retreat, 5 Acre Waterfront Home, Pool, Pier, Fishing & Crabbing
Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Michaels / Easton
9.6 out of 10, Exceptional, 66 reviews
"we had a business trip up in MD - had 8 guys up there with the owner of the company and everyone was very comfortable. The rental property let us know that the pool was closed, but it all worked out great cause the weather was awful. The property/house was fantastic for the 8 of us. Space wise and sleeping it was perfect. Thank you."
Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Michaels / Easton
2 blocks from Bay! Private beach! Boat launch! Kayak! Hike! No cleaning fee!
2 blocks from Bay! Private beach! Boat launch! Kayak! Hike! No cleaning fee!
365-degree waterfront views. Quiet property bordering Blackwater River Refuge.
10.0 out of 10, Exceptional, 2 reviews
"This house is a big surprise for our group, everyone loves it and really enjoyed the trip. All-around water view, th house is spacious with 8 bedrooms, well-decorated and equipped (lots of kitchen gadgets). The host is super easy to communicate as well. Kids had fun time crabbing. Will definitely come back."
365-degree waterfront views. Quiet property bordering Blackwater River Refuge.
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
The price is $499
$846 total
includes taxes & fees
Jun 10 - Jun 11
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
10.0 out of 10, Exceptional, 29 reviews
"👍👍"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, 17 reviews
"We enjoyed our trip, the house was fully equipped and had all the comforts you could need. The water view, watching the birds, the kayak, the dock at sunrise, were our favorite things. We look forward to coming back sometime soon."
The price is $292
$506 total
includes taxes & fees
Jun 16 - Jun 17
Beautiful Waterfront Retreat in Cambridge!
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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.

Other property types in Woolford

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
10.0 out of 10, Exceptional, 5 reviews
"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
Waterfront Getaway with Dock
10.0 out of 10, Exceptional, 25 reviews
"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
Jun 10 - Jun 11
Waterfront Getaway with Dock
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
9.8 out of 10, Exceptional, 67 reviews
"Wonderful house. Well stocked with supplies. Great open floor plan along with a couple separate spaces on the main floor. Our group had 7 adults and our eight grandchildren six and under. Pool has gated access which was a key feature with all our little ones. The owner provided much info regarding things to do in the area. The bedroom spaces worked out great with our mix. We really enjoyed the crab traps and the dock for fishing. It was mostly casting practice but the kids loved it. We enjoyed...
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
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 Homes information

Number of reviews
328
Accommodation
213 Vacation Homes
Lowest Price
$225
Highest Price
$499

Recent reviews of Woolford hotels
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