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Browse Select Woolford Holiday Homes

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, (5)
"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!
Walk to Everything House
10.0 out of 10, Exceptional, (64)
"The house was perfectly located in town in St. Michael’s with off street parking as a bonus. Despite the weather being cold and rainy, we had a lovely time in charming St. Michaels. It was a delightful spot for our annual girls weekend."
Walk to Everything House
Shewell's A-Frame on Mill Creek
10.0 out of 10, Exceptional, (1)
"Beautiful home overlooking the water. Excellent communication with the owners who answered all of my questions quickly. No complaints at all and im Looking forward to returning soon."
Shewell's A-Frame on Mill Creek
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Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (18)
"This house is incredible! Probably the cleanest rental house I have ever stayed in! The house was well stocked and very comfortable. However, we didn’t spend much time in the house because the outside is the real winner! The Crab House has everything to entertain kids and adults for hours! We spent all day in the yard, taking in the beautiful sights! If you are an early riser, like myself and one son, don’t miss the sunrise. So peaceful! If you are looking for crabs while there, Soft & Salty...
The price is £431
per night
23 Jun - 24 Jun
Beautiful Waterfront Retreat in Cambridge!
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
10.0 out of 10, Exceptional, (102)
"Loved the house!"
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
10.0 out of 10, Exceptional, (4)
"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
Spacious River Front Home - 90 minutes from DC with Dock, Kayaks & Paddleboards
9.8 out of 10, Exceptional, (15)
"The house was incredible. My husband loved the master shower! The kids enjoyed the beach and swimming. Our youngest son (39) paddled the creek in the kayak. Our oldest son was able to dock his boat. The house had so many amenities. The kitchen was well stocked. There were games and books for all ages. We hope this home is available whenever we go back to visit family. Thank you, Victoria, for being so gracious!"
Spacious River Front Home - 90 minutes from DC with Dock, Kayaks & Paddleboards
Downtown St. Michaels | Bikes | Kayaks | Private Pier
9.8 out of 10, Exceptional, (20)
"Very clean and large property on scenic river. Only disappointing issues included problems launching kayaks over a tall wall and unfriendly TY cable system. Offset by abundance of great restaurants and peaceful and well maintained home."
Downtown St. Michaels | Bikes | Kayaks | Private Pier
Shewell’s Rambler in the Chesapeake Ranch Estates
9.2 out of 10, Wonderful, (19)
"Nice and super clean. Nice location. We will stay again next time we visit family. "
Shewell’s Rambler in the Chesapeake Ranch Estates
Stylish Victorian in Historic District
10.0 out of 10, Exceptional, (12)
"We all had a great time staying the weekend at the Beautiful house on Belvedere Avenue. This is the third year in a row we all stayed here. It was very close to the center of town where we had some great food and stopped at R & R for a drink. Plenty of space in the house to enjoy each others company. Would highly recommend this place to other people visiting Cambridge."
Stylish Victorian in Historic District
Blue Heron Retreat on the Water
10.0 out of 10, Exceptional, (4)
"Very pleased. Didn't get to use everything offered with my stay. Didn't matter. Definitely would recommend."
Blue Heron Retreat on the Water
Hudson Creek Retreat, 5 Acre Waterfront Home, Pool, Pier, Fishing & Crabbing
Hudson Creek Retreat, 5 Acre Waterfront Home, Pool, Pier, Fishing & Crabbing
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!
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
10.0 out of 10, Exceptional, (30)
"👍👍"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Mid-Century Modern and Marvelous on the Bay
10.0 out of 10, Exceptional, (62)
"The house is a perfect retreat! I watched the sunrise from my bedroom and porch with my coffee each day of our stay. My parents live just 2 doors down. I have been coming to this neighborhood since the 70's. I still love hunting for fossils on the beach. Thank you for allowing us to book this spot!"
Mid-Century Modern and Marvelous on the Bay
Dollhouse in Central Historic St Michaels
9.8 out of 10, Exceptional, (38)
"Cute little place close to town. Perfect for what we wanted."
Dollhouse in Central Historic St Michaels
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
10.0 out of 10, Exceptional, (1)
"Property and location couldn't be better! Host was very accommodating and quick to respond. Will definitely go back!"
The price is £367
per night
25 Jun - 26 Jun
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
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
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 £215
per night
23 Jun - 24 Jun
Waterfront Getaway with Dock
Newly Renovated Secluded Luxury waterfront cottage with private deep water pier!
10.0 out of 10, Exceptional, (66)
"My family had a wonderful stay at Ivy Cove. We were in town for our niece’s wedding and it was close enough to participate in all family activities but far enough away to be a peaceful haven to relax. The house is beautiful. Beds were very comfortable. We really enjoyed the fire pit and game room. The owner was fantastic. We would absolutely stay again in this amazing home."
Newly Renovated Secluded Luxury waterfront cottage with private deep water pier!
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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)
"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)
"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 £215
per night
23 Jun - 24 Jun
Waterfront Getaway with Dock
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
9.8 out of 10, Exceptional, (67)
"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 Holiday Homes information

Number of reviews
473
Accommodation
213 Holiday Homes
Lowest Price
£215
Highest Price
£431

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