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Compare 111 Vacation Homes in Secretary with updated reviews, rates, and availability.

"The Ranch at Royal Oak was a fantastic property. The property was exactly as advertised - gorgeous waterfront estate with a large lawn. Incredibly peaceful. We were looking for a getaway to hit pause and just relax and the ranch Royal Oak was exactly what we needed. Marissa was a great host - incredibly responsive, check in instructions are very clear.and easy to follow. I highly recommend this property for your next getaway."

"I was deciding between booking a hotel or a home and thankful that we decided on this home for our weekend getaway. After visiting the museums in Cambridge, we were welcomed to our home away from home. Very relaxing, comfortable and spacious for our family. Conveniently located to downtown and nice neighborhood. If looking for a home to stay when in the Cambridge area, this is an excellent choice."

Cambridge Vacation Rental | 7BR | 5.5BA | Stairs Required | 10,333 Sq Ft

" October 11-14, 2024, we rented the “Willoughby” for a family reunion. Let me start out by saying this home is amazing. It looks exactly as pictured based on the website photos. It was even better than I expected. If you are considering this property, I highly recommend booking it! Believe me when I say the Willoughby is a rare gem. The location of the home is perfect and extremely private. The grounds are pristine and the view of the water is breathtaking. The home sits on the Hudson...

"Lovely quaint property for two. Exactly as described loved our stay. "

SAR 1,353 total

includes taxes & fees

23 Jan - 24 January 2025

Aerial view of property- river, dock, pergola , pool behind house

"We enjoyed our time at the house very much. We went out to dinner only once and the rest of the time we ate in. We grilled two nights and made a roast one night. The views and the pool were more than you could imagine."

"This property is a phenomenal place to spend time with family and enjoy beautiful St. Michael’s. The house is well stocked and convenient to town. We’d love to come back. "

"This property was exactly what we were looking for our family vacation. Location on the water, the amenities were above and beyond, comfortable beds, and land as far as you could see. The fishing and crabbing was exceptional for all ages. The kids loved crabbing, new to us, caught some turtles as well, all released back. Paddle boarding and kayaking on morning water (like glass), was on the daily. There is a perfect fire pit area to enjoy. The large open concept home is perfect for the...

"The house was just as it was listed!! Our annual family vacation was so much fun here! Plenty of room, very clean, and fully stocked! Peddle boats, kayaks, and pool used daily!! Fire every night!!! Thank you for the wonderful hospitality!!!"

"Listing and photos accurately describe accommodations. We were comfortable and satisfied. A nice rural location for perusing outdoor activities - fishing, hunting, boating, paddling, birdwatching. Good parking for a boat trailer. "

Madison Vacation Rental | 3BR | 2.5BA | Stairs Required | 2,500 Sq Ft

"Wonderful house with great views of water. Everything was as advertised and we had a very relaxing stay. Will definitely consider returning. "

"This property was in a great location for attending the Waterfowl festival. The host thought about each detail and our stay was more than comfortable. "

SAR 1,668 total

includes taxes & fees

1 Jan - 2 January 2025

Denton Vacation Rental | 5BR | 3.5BA | 4,496 Sq Ft | 4 Steps Required

"This large property - inside and outside - was perfect for our family get together. We were a total of 7 adults, 3 children and an infant and there were plenty of bedrooms, bathrooms, dining room space and other areas to hang out in. The pool and fire pit were great for kids and adults, and some of the family enjoyed kayaking. The property adjoining the Choptank River was private and peaceful. The property manager - Julie - went above and beyond to provide us what we needed for a great...

"Kyle was very responsive and a great host! This house is set up to accommodate a large group, but has space for privacy as well. Close to restaurants and shopping, but fully stocked kitchen and linens. Would recommend staying here!! Loved the chickens!!"

"This was the most peaceful and perfect property. I felt like I was on vacation and able to relax! We would definitely return if we are in the area again."

"The perfect Thanksgiving. House was just right for family of three although more people would have been fine too. Lived the crab shack and played lots of pool and ping pong. Kitchen well stocked. Owners were prompt in responding to any questions. We would come back in a heartbeat."

SAR 1,926 total

includes taxes & fees

23 Jan - 24 January 2025

Our home blends into towering pines, lawns & hundreds of feet of waterfront

"We stayed at Saddle House during 2024 Ironman Maryland, with 2 Ironmans competing and lots of support traveling to stay. I was concerned choosing a house about 20 minutes from the start/finish but it was an amazing choice with great bike route access. House is secluded and serene, amazing cleanliness, kitchen with everything you could ever need. Pictures are very accurate to the product you get. Jon was a great help finding things to do, house has incredible resources that support you during...

"The original home is unique and gorgeous and the additions, the sunroom facing sunrises and the lodge style master chef kitchen gave us plenty of room to spread out. The large lawn and driveway gave us plenty of areas to walk the dogs and the beach was a daily swim spot for the dogs. The pool was one of the nicest we have had yet. We love the places with nice pools facing the boats out on the water. We will be back again for sure"