Holiday Rentals in Secretary

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Secretary

Our top choices for Secretary holiday rentals

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (256)
"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

10.0 out of 10, Exceptional, (12)
"The location and apartment were perfect. "
The price is €221
includes taxes & fees
3 Sept - 4 Sept
Sailwinds Loft at Cambridge Creek

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

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

9.6 out of 10, Exceptional, (33)
"This house is awesome - very large and has room for all! It also has some old charm character and features that were really fun, like two "hidden staircases" the kids loved! Bedroom layouts were smartly planned to accommodate large groups and families. The property is truly gorgeous and huge - trails in the woods, lakes, tons of space for yard games and a swing set with two working swings. Parking was abundant, great basketball court and well stocked with the basics! The indoor pool is literally...
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

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

10.0 out of 10, Exceptional, (10)
"Perfect house for a long weekend. Clean, cozy and great communication with Maxine. Would definitely stay here again when I return to Cambridge. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.6 out of 10, Exceptional, (13)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is €319
includes taxes & fees
3 Sept - 4 Sept
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

"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!

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

9.8 out of 10, Exceptional, (7)
"Great House "
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

Waterfront property with private boat ramp and new dock!

9.6 out of 10, Exceptional, (14)
"Thoroughly enjoyed our stay! Cottage was comfortable and very clean with everything we could have needed! "
Waterfront property with private boat ramp and new dock!

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

8.6 out of 10, Excellent, (8)
"Spacious, orderly interior, lovely setting, great amenities: kayaks, fire pit, creek feeds into Chop tank, close to Saint Michaels and Secretary.Big bedrooms with new comfy beds, plenty of bathrooms and showers.Just a lovely place and excellent communication from host."
The price is €562
includes taxes & fees
3 Sept - 4 Sept
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

9.8 out of 10, Exceptional, (132)
"Great house, host and location. Stayed with a larger group and plenty of room!"
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (44)
"Beautifully decorated home, clean and spacious. We really enjoyed the private waterfront and kayak. Would love to come back. "
The price is €385
includes taxes & fees
8 Sept - 9 Sept
Beautiful Waterfront Retreat in Cambridge!

Modern Country Home with Pool and Game Room

9.4 out of 10, Exceptional, (6)
"Nice place. Well accommodated."
Modern Country Home with Pool and Game Room

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

2.0 star property
10.0 out of 10, Exceptional, (7)
"House is clean, renovated, and comfortable. View was gorgeous. Hosts were helpful and timely in communications. Enthusiastically recommend. "
Escape with family or friends to this peaceful, 4-bedroom retreat on the water

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)

Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.

10.0 out of 10, Exceptional, (10)
"This is such a special property. The house, the amenities and then the surprising foodie scene in Easton and St. Michael’s is within minutes. This is our second summer at this property and we are already starting to plan our third!"
Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.

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

10.0 out of 10, Exceptional, (89)
"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

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

10.0 out of 10, Exceptional, (89)
"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)

Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

9.8 out of 10, Exceptional, (49)
"We absolutely loved your place and it was perfect for our family. We would love to come back and stay next summer!"
Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Secretary Hotel Reviews

Find out more about Secretary

Find out more about Secretary

Everything you need to know about Secretary holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Secretary holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Secretary holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Secretary holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Secretary. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Secretary holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Secretary holiday rentals we have selected for you start as low as €221 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Secretary rentals

At Expedia, we put the best Secretary holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Secretary rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Secretary holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Secretary. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Secretary?

Yes, there are holiday rentals close to the most popular sights in Secretary, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Secretary has to offer?

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina: This holiday home rental outside of Secretary is located in the city centre, and has a garden, a selection of games and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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 wider area, you’ll find Dorchester County Visitors Center and Choptank River Lighthouse.

What’s a holiday rental in Secretary like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Secretary. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll have everything you want. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for a family getaway.