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Check prices for these dates

Next weekend
25 Rab. II - 27 Rab. II
In two weeks
2 Jum. I - 4 Jum. I
In one month
16 Jum. I - 18 Jum. I
In two months
13 Jum. II - 15 Jum. II

Compare 136 Vacation Homes in Secretary with updated reviews, rates, and availability.

Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak
Exterior

Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

9.8 out of 10, Exceptional, (40)
"Our group of longtime friends from different states wanted a convenient location to meet for a weekend getaway. The Eastern Shore was a good location and this property was a wonderful and comfortable place for our group. The house was spacious and had plenty of areas for members of the group to enjoy all together or in smaller conversation groups. Our group meals were easy to prepare in the large and well-equipped kitchen. The dining room easily accommodated our group for our dinners and the...
Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Outdoor pool

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

10.0 out of 10, Exceptional, (86)
"6 women for the 6 bedroom home. The house was great for our weekend. The only complaint was that the weather did not allow for more outdoor activities, though we had plenty of space inside to enjoy ourselves. The house has all the amenities and more. "
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC
4 bedrooms, desk, iron/ironing board, free WiFi

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)
"Very clean, well stocked with towels, paper products and everything else you need. Lots of space for a large group. I liked the master bedroom on the first floor. Having a second coffee maker upstairs is a nice touch. Walking distance to downtown. "
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Bar (on property)

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

10.0 out of 10, Exceptional, (7)
"The Lighthouse cottage was super clean & comfortable, beautifully decorated and stocked with supplies, and located on a lovely block overlooking water l. As a bonus, it was walking distance from downtown’s many shops and restaurants. "
The price is SAR 638
SAR 1,436 total
includes taxes & fees
20 Apr - 21 Apr
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Stylish Home on the Choptank River (with Tidal Beach)
Fridge, microwave, oven, stovetop

Stylish Home on the Choptank River (with Tidal Beach)

10.0 out of 10, Exceptional, (32)
"A beautiful and serene setting mapping the contours of nature, tranquility & relaxation. Steven is an exceptional host."
Stylish Home on the Choptank River (with Tidal Beach)
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Smart TV, books, printers

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

9.8 out of 10, Exceptional, (9)
"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
Fridge, microwave, oven, stovetop

Waterfront Getaway with Dock

10.0 out of 10, Exceptional, (40)
"Great location for exploring the Eastern Shore. Beautiful dock! "
The price is SAR 863
SAR 1,046 total
includes taxes & fees
21 Apr - 22 Apr
Waterfront Getaway with Dock
Beautiful Waterfront Retreat in Cambridge!
Fridge, microwave, oven, stovetop

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (33)
"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."
The price is SAR 1,032
SAR 1,933 total
includes taxes & fees
21 Apr - 22 Apr
Beautiful Waterfront Retreat in Cambridge!
Minutes from Downtown Easton and St. Michaels | Pool | Kayaks | Private Dock
Smart TV, books

Minutes from Downtown Easton and St. Michaels | Pool | Kayaks | Private Dock

10.0 out of 10, Exceptional, (16)
"Our 5th year traveling to the eastern shore of Maryland. The house was great. Loved everything about Pool"
Minutes from Downtown Easton and St. Michaels | Pool | Kayaks | Private Dock
Minutes from Downtown Cambridge | Private Dock | Pool | Kayaks
Smart TV, fireplace, video games, DVD player

Minutes from Downtown Cambridge | Private Dock | Pool | Kayaks

9.4 out of 10, Exceptional, (16)
"Very well equipped home at a beautiful location overlooking the water. The pool was a real treat for the kids in our group. The property manager was in regular communication and quickly dealt with one item that needed attention."
Minutes from Downtown Cambridge | Private Dock | Pool | Kayaks
St. Michaels Waterfront Home
Property grounds

St. Michaels Waterfront Home

9.8 out of 10, Exceptional, (26)
"We had a wonderful stay. Check in and out was very easy. The place was clean and well maintained. Very peaceful spot on the water. "
St. Michaels Waterfront Home
Eagle Haven - Waterfront Estate on the Choptank with Pool and Pier - Sleeps 18
Fridge, microwave, oven, stovetop

Eagle Haven - Waterfront Estate on the Choptank with Pool and Pier - Sleeps 18

10.0 out of 10, Exceptional, (74)
"We were very impressed with the property and your place was very clean and had just about everything we needed. The location is wonderful and close to the event that we stayed in Cambridge for. I would definitely recommend this for others and will likely be renting again"
Eagle Haven - Waterfront Estate on the Choptank with Pool and Pier - Sleeps 18
Modern Country Home with Pool and Game Room
Property grounds

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
Sunset Breezes - quiet waterfront retreat
Property grounds

Sunset Breezes - quiet waterfront retreat

10.0 out of 10, Exceptional, (36)
"Lovely property. Right on the water. Pretty detached (20 minute drive to Cambridge, the nearest town). Very comfortable. Appreciated the opportunity to use the fire pit for s'mores and the fresh eggs from the chickens who have their own coop a few feet away from the house!"
Sunset Breezes - quiet waterfront retreat
Luxury Waterfront Retreat with in ground pool and close to town
Fridge, microwave, oven, stovetop

Luxury Waterfront Retreat with in ground pool and close to town

10.0 out of 10, Exceptional, (34)
"12 of my friends and i stayed here for my birthday, not only did the hosts leave me a nice birthday gift, but a wonderful place to hang out for a weekend. The place is immaculate and well thought out. They paid attention to every detail! The kitchen is fully stocked so that we could cook for and feed all 13 of us. The entire weekend people kept telling me it was so comfortable, so clean, surprisingly well stocked, beautiful, fun to be in, etc.! Will definitely return! Mindy was very responsive...
Luxury Waterfront Retreat with in ground pool and close to town
Downtown Oxford | Charming | Pet Friendly
Exterior

Downtown Oxford | Charming | Pet Friendly

9.8 out of 10, Exceptional, (38)
"A lovely quaint Oxford home in a great location. Quiet, with views of the Harbor and the Tred Avon River from the street. A first floor bedroom and 2 upstairs, make it possible to include older parents in a family stay. To relax together with coffee in the morning and share wine porch side in the afternoon is an experience that no hotel can duplicate."
Downtown Oxford | Charming | Pet Friendly
A Luxury Home located in Easton with Water VIEWS! Close to Oxford/St. Michaels
Smart TV, table tennis

A Luxury Home located in Easton with Water VIEWS! Close to Oxford/St. Michaels

10.0 out of 10, Exceptional, (18)
"It’s in a tranquil, bucolic setting that is relaxing to come back to after a day out enjoying activities. Lovely home all around."
A Luxury Home located in Easton with Water VIEWS! Close to Oxford/St. Michaels
Luxury on the river, steps to downtown &boat ramp!
Fridge, microwave, oven, stovetop

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 SAR 1,122
SAR 2,013 total
includes taxes & fees
20 Apr - 21 Apr
Luxury on the river, steps to downtown &boat ramp!
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals
Fridge, microwave, oven, stovetop

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!
Terrace/patio

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

9.4 out of 10, Exceptional, (22)
"This property offered a truly magnificent stay. We were delighted by its gorgeous and clean environment, the peaceful atmosphere, and the impressive array of amenities. Finding a place that could comfortably accommodate our group of 20 for a two-day family and friends trip with a private indoor pool, hot tub, billiard table, table tennis, kayaks, and a private deck exceeded our expectations. The accommodations were spacious and spotless upon arrival, and we appreciated the ample supply of...
Waterfront Cambridge Gem w/ Hot Tub, Pool & 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.
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Other property types in Secretary

Family and Pet-Friendly, Waterfront with Pier
Exterior

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (244)
"The only thing I can say is that the online listing really doesn’t do justice to how amazingly stunning Rob & Clarissa’s place is. My family and I decided last minute that we wanted to spend a weekend on the bay. I never expected it to be so beautiful! We got there late in the evening and we were speechless when we woke up to the most beautiful view of the water. My son had an amazing time between playing in the loft or in the playhouse outside, kayaking, and paddle boating. My parents “settled”...
Family and Pet-Friendly, Waterfront with Pier
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Smart TV, books, printers

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

9.8 out of 10, Exceptional, (9)
"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
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Bar (on property)

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

10.0 out of 10, Exceptional, (7)
"The Lighthouse cottage was super clean & comfortable, beautifully decorated and stocked with supplies, and located on a lovely block overlooking water l. As a bonus, it was walking distance from downtown’s many shops and restaurants. "
The price is SAR 638
SAR 1,436 total
includes taxes & fees
20 Apr - 21 Apr
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
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.