Holiday Rentals in Secretary

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Our top choices for Secretary holiday rentals

10.0 out of 10, Exceptional, (7)
The price is €223
includes taxes & fees
27 Jan - 28 Jan 2026
Station House East: Upscale Loft in the Historic District Cambridge, MD
9.8 out of 10, Exceptional, (11)
"This was such a cozy, comfortable space for a girls weekend away. We loved the charm of the old building paired with thoughtful amenities. "
United States
Lauren V.
The price is €307
includes taxes & fees
12 Jan - 13 Jan 2026
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
10.0 out of 10, Exceptional, (10)
"Just a beautiful place. I would stay here again. Everything was walking distance. "
United States
Sylvie G.
The price is €307
includes taxes & fees
5 Jan - 6 Jan 2026
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
9.6 out of 10, Exceptional, (20)
"The place was wonderful beautiful views of harbor, extremely clean and well appointed. Great restaurants we ate at RAR, great beer and food. Christopher’ Corner great dinner food fabulous and cocktails, highly recommend. Blackwater Cafe wonderful breakfast. "
United States
deb j.
The price is €302
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Apartment in Cambridge

Sailwinds Loft at Cambridge Creek
10.0 out of 10, Exceptional, (24)
"What a great place to relax after exploring and enjoying the area. Definitely will visit again "
United States
Chris S.
The price is €222
includes taxes & fees
29 Dec - 30 Dec
Sailwinds Loft at Cambridge Creek
8.4 out of 10, Very good, (6)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
The price is €254
includes taxes & fees
5 Jan - 6 Jan 2026
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
10.0 out of 10, Exceptional, (50)
"Beautiful place! Loved all the activities, will return in the future! Our family and friends had a blast! Thank you so much!!"
United States
Karen L.
The price is €325
includes taxes & fees
4 Jan - 5 Jan 2026
Beautiful Waterfront Retreat in Cambridge!

Holiday Home in Woolford

Waterfront Getaway with Dock
10.0 out of 10, Exceptional, (51)
"Great place, will stay again"
United States
Matt S.
The price is €243
includes taxes & fees
28 Dec - 29 Dec
Waterfront Getaway with Dock

Holiday Home in Dorchester County

Sunset Breezes - quiet waterfront retreat
10.0 out of 10, Exceptional, (41)
"Good time with my friends "
United Kingdom
Oleg L.
The price is €297
includes taxes & fees
30 Dec - 31 Dec
Sunset Breezes - quiet waterfront retreat
10.0 out of 10, Exceptional, (14)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
The price is €454
includes taxes & fees
28 Dec - 29 Dec
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
8.8 out of 10, Excellent, (9)
"This home was everything we needed and more! It was spacious, clean and a beautiful location! There was a leak in the ceiling and the owners were very responsive and fixed it right away. Definitely recommend this stay."
United States
Priscilla A.
The price is €556
includes taxes & fees
2 Jan - 3 Jan 2026
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
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

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 €222 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?

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks: This holiday home rental outside of Secretary is located in a rural location, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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.