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Compare 107 Vacation Homes in Secretary with updated reviews, rates, and availability.

Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals

9.6 out of 10, Exceptional, (19)
"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!!!"
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals

Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

2.0 star property
9.6 out of 10, Exceptional, (4)
"The house was very clean and was great for our home base while visiting family in St. Michael’s. The owner was very response and friendly. The house included all basic amenities and then some! The owner really took the time and care preparing this place for guests. Downtown Cambridge is a short drive and a cute little town with shops and restaurants. We didn’t have a ton of time to explore downtown but plan to on our next stay! "
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

Stylish Home on the Choptank River (with Tidal Beach)

10.0 out of 10, Exceptional, (31)
"We just finished a great three day stay at this property. The place was spotless and the location to the towns of the eastern shore was perfect. Wonderful to look out and see the river lazily roll by. The"
Stylish Home on the Choptank River (with Tidal Beach)

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

9.6 out of 10, Exceptional, (20)
"Terrific house, beautiful scenery, property management was very responsive and helpful. Would stay again. Thank you. "
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

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

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

10.0 out of 10, Exceptional, (1)
"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. "
Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock

Turn Winter Blues Into Blissful Views, Book Now!

9.8 out of 10, Exceptional, (7)
"We truly loved our stay! The home was super comfortable and well stocked for making Thanksgiving dinner for 6. We loved just looking out at the geese, swans and blue herons ! Really lovely. We’ll be back!"
Turn Winter Blues Into Blissful Views, Book Now!

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

10.0 out of 10, Exceptional, (24)
"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."
RANCH AT ROYAL OAK- Exclusive waterfront pool pier

NEW! Gorgeous Waterfront Estate with pool, beach and dock

9.6 out of 10, Exceptional, (4)
"The property was perfect for our family get together. We had a baby, toddler, preschooler, elementary and teens, moms, dads and grandparents. There was a place for everyone. Having a pack n’ play available would have been nice, but we procured one elsewhere. The property was large and felt very private, but Cambridge was just a quick drive."
NEW! Gorgeous Waterfront Estate with pool, beach and dock

Downtown Oxford | Outdoor Dining | Character Filled

Downtown Oxford | Outdoor Dining | Character Filled

Luxury Waterfront Retreat with in ground pool and close to town

10.0 out of 10, Exceptional, (32)
"Beautiful house and location to getaway with peace and quiet. Still within 5-10 minutes of anything you need including downtown Cambridge. WillDefinitely come Back!"
The price is SAR 1,313
SAR 2,501 total
includes taxes & fees
4 Feb - 5 Feb
Luxury Waterfront Retreat with in ground pool and close to town

Modern Country Home with Pool and Game Room

9.2 out of 10, Wonderful, (5)
"Awesome place ! We had some family visit us there and everyone loved the place too. The toilet paper holder in the half bath needs to be reattached to the wall. Also … I noticed the drain pipe closest to the hot tub is separated at the top. "
Modern Country Home with Pool and Game Room

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

2.0 star property
10.0 out of 10, Exceptional, (1)
The price is SAR 563
SAR 1,801 total
includes taxes & fees
4 Feb - 5 Feb
Relaxing, spacious 5BR house on the Hudson Creek in charming Cambridge

Warwick Farms Waterfront Retreat! Solitude and relaxation on the Warwick River

10.0 out of 10, Exceptional, (10)
"Our extended family of nine spent a week at Warwick Farms in July, 2024. There was space for all of us to be together for meals, puzzles, movies, and games...and also plenty of room for us to spread out and do our own thing. The pool was wonderful, the view was amazing, and the amenities were superb. We appreciated the cleanliness, the plentiful towels, the wildlife sightings, and the availability of the kayaks, etc. We had one small issue during the stay, but the property manager and host...
Warwick Farms Waterfront Retreat! Solitude and relaxation on the Warwick River

The Blackwater refuge country house on a quiet 12 acres

9.8 out of 10, Exceptional, (9)
"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

Escape with family or friends to this peaceful, 4-bedroom retreat on the water

2.0 star property
10.0 out of 10, Exceptional, (2)
"The home was lovely and cozy with all the amenities needed for a comfortable stay.Sunsets on the river were amazing and we saw a variety of wildlife including a bald eagle, a fox, herons and lots of Canada geese.We’d like to return in warmer weather to enjoy the screened porch and water activities."
Escape with family or friends to this peaceful, 4-bedroom retreat on the water

Multi-Generational Waterfront Retreat with Pool. No cleaning fees!

10.0 out of 10, Exceptional, (62)
"The photos of this property do not tell the whole story. This home is incredible!!!! When we arrived, the house was clean, clearly labeled, well stocked, and has super responsive owners. The property has everything!!! Luxurious and comfortable furnishings, beautiful touches throughout, a dock for fishing and watching sunsets, striking wildlife, a perfect pool setup and a terrific game room. We had kids aged 18 to 3, and everyone had a blast!!!!! This place is a hit with young people and those...
Multi-Generational Waterfront Retreat with Pool. No cleaning fees!

Cozy 2BR Home near Idlewild Park

10.0 out of 10, Exceptional, (3)
"The apartment was perfect. Spotless, well maintained and equipped. The owners had coffee, fruit bowl and goodies waiting.I would highly recommend this charming and centrally located rental, it’s very likely we would stay here again.Thanks Lynda and Ron."
Cozy 2BR Home near Idlewild Park

New listing! Riverside Retreat on the Choptank River

10.0 out of 10, Exceptional, (3)
"Great location, spotless and comfy. "
New listing! Riverside Retreat on the Choptank River

Beautiful Peaceful Home

10.0 out of 10, Exceptional, (2)
"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."
The price is SAR 1,313
SAR 1,757 total
includes taxes & fees
1 Mar - 2 Mar
Beautiful Peaceful Home
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 Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals

9.6 out of 10, Exceptional, (19)
"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!!!"
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals

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

9.6 out of 10, Exceptional, (20)
"Terrific house, beautiful scenery, property management was very responsive and helpful. Would stay again. Thank you. "
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

2.0 star property
9.6 out of 10, Exceptional, (4)
"The house was very clean and was great for our home base while visiting family in St. Michael’s. The owner was very response and friendly. The house included all basic amenities and then some! The owner really took the time and care preparing this place for guests. Downtown Cambridge is a short drive and a cute little town with shops and restaurants. We didn’t have a ton of time to explore downtown but plan to on our next stay! "
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC
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.