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Compare 112 Vacation Homes in Secretary with updated reviews, rates, and availability.

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Cambridge Vacation Rental | 7BR | 5.5BA | Stairs Required | 10,333 Sq Ft

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

9.6 out of 10, Exceptional, (17)
" 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...
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Luxury on the river, steps to downtown &boat ramp!
Exterior

Luxury on the river, steps to downtown &boat ramp!

10.0 out of 10, Exceptional, (5)
"Stayed for three nights with a few friends with a focus on birding. The house is in a great location for "
The price is AED 797
AED 1,620 total
includes taxes & fees
2 Dec - 3 Dec
Luxury on the river, steps to downtown &boat ramp!
Beautiful Peaceful Home
Living area

Beautiful Peaceful Home

7.4 out of 10, Good, (3)
"Owner canceled the day before with no notice"
Beautiful Peaceful Home
Travelers Rest Spacious 5BR Pool riverfront Pier charming Easton Saint Michaels
Miscellaneous

Travelers Rest Spacious 5BR Pool riverfront Pier charming Easton Saint Michaels

2.0 star property
10.0 out of 10, Exceptional, (1)
"We would love to return to Travelers Rest! Spacious home with separate master suites, waterfront views, large efficient kitchen, large private property, fairly isolated and within easy striking distance to Easton and St Michaels. We’ve rented many homes in this area and Travelers Rest is among the best. "
Travelers Rest Spacious 5BR Pool riverfront Pier charming Easton Saint Michaels
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Aerial view

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

10.0 out of 10, Exceptional, (7)
"This house is huge and has lots of different indoor and outdoor gathering spaces so the kids and adults in our group of three families didn’t have to be on top of each other in one living space the whole time. Big firepit area and huge lawn were great, and we enjoyed the kayaks and canoe. There’s a place to buy fresh crabs, oysters, and shrimp very close by, and the house has everything you need for a crab night. The owner was incredibly responsive and kind."
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Waterfront Getaway with Dock
Property grounds

Waterfront Getaway with Dock

10.0 out of 10, Exceptional, (37)
"Every morning I made coffee, lit the fire pit on the dock and spent at least from 30 minutes before sunrise to 30 after. Used Merlin to identify bird calls. Heard and saw bald eagles, a belted kingfisher and an eastern bluebird. Watched a great blue heron fishing. Heard many many different birds. Truly an awesome location to slow down and enjoy the moment "
The price is AED 845
AED 1,024 total
includes taxes & fees
15 Dec - 16 Dec
Waterfront Getaway with Dock
Cottage on Cabin Creek
Beach

Cottage on Cabin Creek

10.0 out of 10, Exceptional, (100)
"I highly recommend staying here for a cozy couples weekend. It was absolutely beautiful and quiet. The host was so nice and made us feel welcome. I can’t wait to stay here again."
The price is AED 918
AED 1,332 total
includes taxes & fees
11 Dec - 12 Dec
Cottage on Cabin Creek
Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks
Aerial view of property- river, dock, pergola , pool behind house

Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks

9.8 out of 10, Exceptional, (6)
"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."
Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks
Autumn Charm Beautiful Waterfront Retreat Near Historic St. Michaels & Royal Oak
Property grounds

Autumn Charm Beautiful Waterfront Retreat Near Historic St. Michaels & Royal Oak

9.8 out of 10, Exceptional, (37)
"Great rental experience. Barb was fantastic at communicating. The house was perfect for our group, including some adults and some young children. Yard and dock were a blast for playing and fishing. "
Autumn Charm Beautiful Waterfront Retreat Near Historic St. Michaels & Royal Oak
Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock
Pool

Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock

Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock
The Blackwater refuge country house on a quiet 12 acres
Exterior

The Blackwater refuge country house on a quiet 12 acres

9.8 out of 10, Exceptional, (8)
"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. "
The Blackwater refuge country house on a quiet 12 acres
Bayfront Gem w/ Amazing Water Views + Pond!
Madison Vacation Rental | 3BR | 2.5BA | Stairs Required | 2,500 Sq Ft

Bayfront Gem w/ Amazing Water Views + Pond!

10.0 out of 10, Exceptional, (12)
"Wonderful house with great views of water. Everything was as advertised and we had a very relaxing stay. Will definitely consider returning. "
Bayfront Gem w/ Amazing Water Views + Pond!
Cozy 2BR Home near Idlewild Park
Living area

Cozy 2BR Home near Idlewild Park

10.0 out of 10, Exceptional, (2)
"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. "
Cozy 2BR Home near Idlewild Park
Relaxing, spacious 5BR house on the Hudson Creek in charming Cambridge
Room

Relaxing, spacious 5BR house on the Hudson Creek in charming Cambridge

2.0 star property
The price is AED 441
AED 1,643 total
includes taxes & fees
27 Nov - 28 Nov
Relaxing, spacious 5BR house on the Hudson Creek in charming Cambridge
4 bdrm, 3 bath, 2,700 sqft house on 1 acre with chickens and fenced in back yard
Living area

4 bdrm, 3 bath, 2,700 sqft house on 1 acre with chickens and fenced in back yard

2.0 star property
4 bdrm, 3 bath, 2,700 sqft house on 1 acre with chickens and fenced in back yard
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
Pool

Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F

10.0 out of 10, Exceptional, (1)
"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."
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
Beautiful Waterfront Retreat in Cambridge!
Exterior

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (31)
"This house exceeded our expectations in every way. The kitchen is large and well-appointed, the beds are comfortable, and the peace and quiet is priceless. We enjoyed morning coffee in the sunroom, table tennis in the crab house, sunsets from the dock, and stargazing at the firepit. If you desire peace and quiet this house is a perfect choice!"
The price is AED 1,010
AED 1,884 total
includes taxes & fees
1 Dec - 2 Dec
Beautiful Waterfront Retreat in Cambridge!
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Our home blends into towering pines, lawns & hundreds of feet of waterfront

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

9.8 out of 10, Exceptional, (71)
"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...
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Amazing Waterfront Retreat On The Chesapeake Bay Private Pool Private Beach
Aerial property view

Amazing Waterfront Retreat On The Chesapeake Bay Private Pool Private Beach

9.8 out of 10, Exceptional, (55)
"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"
Amazing Waterfront Retreat On The Chesapeake Bay Private Pool Private Beach
Modern St. Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks & More
Baja Deck with umbrella- sit in pool on plastic adirondack chairs and read!

Modern St. Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks & More

10.0 out of 10, Exceptional, (129)
"Wonderful home for our girl's weekend getaway. Beautiful property on the water and close to Easton and St Michael's"
Modern St. Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks & More
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.
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Other property types in Secretary

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Cambridge Vacation Rental | 7BR | 5.5BA | Stairs Required | 10,333 Sq Ft

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

9.6 out of 10, Exceptional, (17)
" 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...
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Aerial view

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

10.0 out of 10, Exceptional, (7)
"This house is huge and has lots of different indoor and outdoor gathering spaces so the kids and adults in our group of three families didn’t have to be on top of each other in one living space the whole time. Big firepit area and huge lawn were great, and we enjoyed the kayaks and canoe. There’s a place to buy fresh crabs, oysters, and shrimp very close by, and the house has everything you need for a crab night. The owner was incredibly responsive and kind."
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Waterfront Getaway with Dock
Property grounds

Waterfront Getaway with Dock

10.0 out of 10, Exceptional, (37)
"Every morning I made coffee, lit the fire pit on the dock and spent at least from 30 minutes before sunrise to 30 after. Used Merlin to identify bird calls. Heard and saw bald eagles, a belted kingfisher and an eastern bluebird. Watched a great blue heron fishing. Heard many many different birds. Truly an awesome location to slow down and enjoy the moment "
The price is AED 845
AED 1,024 total
includes taxes & fees
15 Dec - 16 Dec
Waterfront Getaway with 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.