Woolford Vacation Rentals

"The house was great and nice area!"

"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!!!"

"Really enjoyed the house and weekend."

"This place was just what my family needed to reconnect. Amazing views and atmosphere"

"Beautiful view!!! Lovely home!! We so thoroughly enjoyed our stay and hope that this is just one of many visits. Thank you!"

"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!"

"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."

"This was a great spot to come and visit. The dock gave the ability to crab and fish whenever. The house and view of the water were amazing. The only downfall for us was the amount of jelly fish so we did not get in the water much. We did bring our boat and launched it right down the road. We are out at the local restaurants and the community was welcoming. We drove around and saw the Harriet Tubman Underground Railroad and visited Cambridge many times."

"This house and its serene surroundings are truly spectacular! All the comforts of home and the home is well loved. Secluded but close to center of Town. Only thing we missed is more queen size beds. Very clean and check in was so easy. Owner gave us tour of the house and some history of the area. Would definitely come back again!"

"Property is excellent. Spacious and clean and suitable for pups (fenced in backyard)! Pretty place with short walk to dock for sunset and Doc’s (food is good). Bed and bathroom comfy. Grocery delivery worked really well - needed to re-supply basic paper goods for family. Would stay here again! Had some difficulty with Amazon packages as rental does not have a USPS receptacle. Post Office would not deliver. Maybe they can address this. Communication with rental company easy and gracious!...

"This is a great property. It was comfortable, clean and spacious. The amenities of bikes and kayaks and a canoe made our stay very enjoyable. Close to downtown St. Michaels but on a quiet inlet. We really enjoyed our stay. Management company was readily available and highly responsive as well."

"We are a group of mid 50s ladies that went to Jr High and High School together. We do an annual "girls" trip and usually head to Deep Creek Lake or Ocean City where some of us own second homes. We decided to switch things up this year and found this amazing rental. From the moment we walked in the door and saw the lovely note and goodies that were left for us - to the beautiful decor and gorgeous bedrooms. There was absolutely nothing missed in this rental. Kitchen fully stocked AND MORE!!! The...

"This house is amazing on a nice quiet street. We enjoyed our stay as it felt like we were home. Clean and cozy a lot of extra room we will be back next year for sure."

"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,...

"Really enjoyed our time there. Very relaxing. Comfortable home. All amenities there. Especially loved the windows..."

"Great house close to the lodge!"

"An amazing, secluded property that is perfect for a family or friends getaway. The rooms are clean, comfortable, and there were plenty of bathrooms. The property could improve by having additional toilet paper, shower toiletries, and towels, but the kitchen was very well stocked and there was plenty of seating. It really is a great house."

"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!"

"We had a great time. The pool was a big hit and all the common areas in the house gave us plenty of room to spread out. The game room was super, also. A few things that would make it even greater: about half a dozen cockroaches and other bugs were found in the house; lack of instruction manuals for appliances and sauna; exterior doors very difficult to lack; comforter in bedroom 1 smelled like dogs. Matt was very helpful and responsive to questions"

"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!"

"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...

"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."