Secretary Vacation Rentals

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Check prices for these dates

In two weeks
Oct 10 - Oct 12
In two months
Nov 21 - Nov 23
In three months
Dec 19 - Dec 21
In four months
Jan 16 - Jan 18

Vacation Rentals in Secretary

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.6 out of 10, Exceptional, (15)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is ￥23,067
￥52,057 total
includes taxes & fees
Sep 29 - Sep 30
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Exterior detail

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

10.0 out of 10, Exceptional, (11)
"Really nice property. Relaxing weekend. Stayed here with my daughter for two nights. We had a great time. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Family and Pet-Friendly, Waterfront with Pier
Exterior

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (257)
"It is a perfect spot to relax and enjoy the water. We will book again if we are back that way. "
Family and Pet-Friendly, Waterfront with Pier
Sailwinds Loft at Cambridge Creek
Private kitchen

Sailwinds Loft at Cambridge Creek

10.0 out of 10, Exceptional, (15)
"The location and apartment were perfect. "
The price is ￥23,067
￥37,860 total
includes taxes & fees
Sep 29 - Sep 30
Sailwinds Loft at Cambridge Creek
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Outdoor pool, a heated pool

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

9.8 out of 10, Exceptional, (74)
"We sought a large home for a special family birthday, with multiple bedrooms, roomy eating and living areas, and water access for recreation. This house met all our requirements and more. Our grandchildren, from teen to preschool, loved the multiple kayaks, the crab traps, roasting marshmallows at the fire pit, swimming in the heated pool, finding oyster shells along the shoreline. We visited Annapolis for a sail and sightseeing, even though it meant driving back over the Bay bridge, and we...
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
Outdoor pool

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

9.8 out of 10, Exceptional, (7)
"Great House "
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Marina

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

10.0 out of 10, Exceptional, (93)
"Beautiful home in a quiet community. "
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Station House East: Upscale Loft in the Historic District Cambridge, MD
Marina

Station House East: Upscale Loft in the Historic District Cambridge, MD

The price is ￥9,434
￥38,731 total
includes taxes & fees
Sep 29 - Sep 30
Station House East: Upscale Loft in the Historic District Cambridge, MD
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
Dining

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

10.0 out of 10, Exceptional, (26)
"Wow, what a homerun of a vacation house - it had everything we needed and more. We had the best time and hope to be back soon."
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
Thorneton Point Estate
Interior

Thorneton Point Estate

9.6 out of 10, Exceptional, (20)
"Beautiful, well-maintained property in a gorgeous waterside setting. "
Thorneton Point Estate
Waterfront Getaway with Dock
Fridge, microwave, oven, stovetop

Waterfront Getaway with Dock

10.0 out of 10, Exceptional, (51)
"Great location with everything you may need. It is close to restaurants and Emily’s produce.2nd time staying and will be back again. "
The price is ￥34,229
￥41,488 total
includes taxes & fees
Sep 28 - Sep 29
Waterfront Getaway with Dock
Downtown St. Michaels | Bikes | Kayaks | Private Pier
Smart TV, fireplace, books

Downtown St. Michaels | Bikes | Kayaks | Private Pier

10.0 out of 10, Exceptional, (33)
"Lovely home in a beautiful location. Super convenient to everything and very well-appointed and comfortable. Would definitely stay here again!"
Downtown St. Michaels | Bikes | Kayaks | Private Pier
Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)
Fridge, microwave, oven, stovetop

Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

10.0 out of 10, Exceptional, (90)
"This property is even prettier in person!! We have a huge extended family and there was plenty of space for everyone. The host and property manager both made themselves available to answer any questions and responded very quickly. Excellent trip - we would love to stay again in the future!"
Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Marina

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

8.8 out of 10, Excellent, (5)
"The place was very clean and in the most perfect spot in downtown Cambridge. We had a wedding walking distance from this place. Jen is a very responsive and accommodating host!"
The price is ￥17,858
￥44,169 total
includes taxes & fees
Sep 29 - Sep 30
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Short drive to Downtown Cambridge | Private Dock | Pool | 16.5 Acres | Guest Hou
Dining

Short drive to Downtown Cambridge | Private Dock | Pool | 16.5 Acres | Guest Hou

9.4 out of 10, Exceptional, (3)
"Very beautiful property with clean rooms. Very responsive property management. Unfortunately the Outdoor grill and the dock light was not functional and the owner did bot resolve it during our stay. Hopefully they will take care of them before the next guest arrives."
Short drive to Downtown Cambridge | Private Dock | Pool | 16.5 Acres | Guest Hou
Beautiful Waterfront Retreat in Cambridge!
Interior

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (47)
"Beautifully decorated home, clean and spacious. We really enjoyed the private waterfront and kayak. Would love to come back. "
The price is ￥33,083
￥66,460 total
includes taxes & fees
Sep 28 - Sep 29
Beautiful Waterfront Retreat in Cambridge!
Stylish Home on the Choptank River (with Tidal Beach)
Property grounds

Stylish Home on the Choptank River (with Tidal Beach)

10.0 out of 10, Exceptional, (38)
"We really enjoyed our stay. The house has everything needed and the sunrises are beautiful."
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

9.4 out of 10, Exceptional, (20)
"The house was very nice, the host was very responsive! The outside was nice, only down side lots of mosquitos but that’s expected. "
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Minutes from Downtown Easton and St. Michaels | Pool
Smart TV

Minutes from Downtown Easton and St. Michaels | Pool

10.0 out of 10, Exceptional, (2)
"House was perfect for 5 adults and infant. Everyone had ample space but could come together. Property was spotless. Pool and dock were wonderful. Landscaping needs attention and it would have been nice to have a fire pit for the evenings. Otherwise a great place and space!!"
Minutes from Downtown Easton and St. Michaels | Pool
"Belle Aire Landing" a Large Beautiful Waterfront Estate! Under New Management!
Fridge, microwave, oven, stovetop

"Belle Aire Landing" a Large Beautiful Waterfront Estate! Under New Management!

3.0 star property
10.0 out of 10, Exceptional, (2)
"Clean, well-appointed kitchen. Loved the crab shack!! Would highly recommend. Used the kayaks and canoe. The pool was perfect! The property is beautiful. Highly reccomend"
"Belle Aire Landing" a Large Beautiful Waterfront Estate! Under New Management!
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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Top Secretary Hotel Reviews

Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge

10/10 Excellent
"This is my favorite place to stay in Cambridge. Affordable and the staff is always so friendly. "
Ryan 4-night trip
Posted 2 days ago
Comfort Inn & Suites Cambridge

Find out more about Secretary

Find out more about Secretary

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Frequently asked questions

Are there vacation rentals in Secretary?

Yes, there are vacation rentals near well known local attractions in Secretary, or you can go with a secluded option if you'd like a relaxing place to stay.

What's the top vacation rental in Secretary?

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock: Visitors like this Secretary vacation home rental. It is located on a river and has an outdoor pool, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and an arcade game room.

What’s there to see and do in Secretary?

While exploring the area, visit family-friendly sights like Easton Cycle and Sport, or get outside and enjoy nature at Long Wharf Park. In the larger area, you’ll find Dorchester County Visitors Center and Choptank River Lighthouse.

What’s a vacation rental in Secretary like?

Vacation rentals are private properties you can book for short or long periods in Secretary. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll feel right at home. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from public hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for families.