Secretary Holiday Rentals

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Check prices for these dates

Tonight
25 Oct - 26 Oct
Tomorrow
26 Oct - 27 Oct
Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov

Holiday Rentals in Secretary

Marina
Station House East: Upscale Loft in the Historic District Cambridge, MD
Station House East: Upscale Loft in the Historic District Cambridge, MD
10.0 out of 10, Exceptional, (1)
"Location very convenient, flat beautiful, clean, very friendly, respo sive and accommodating hostess! Thank you!"
United States
Solveig S.
The price is NZ$620
includes taxes & fees
28 Oct - 29 Oct
Station House East: Upscale Loft in the Historic District Cambridge, MD
Outdoor pool, a heated pool
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
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...
United States
Ronald S.
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Exterior detail
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
10.0 out of 10, Exceptional, (13)
"Really nice property. Relaxing weekend. Stayed here with my daughter for two nights. We had a great time. "
United States
Dara M.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Exterior
Family and Pet-Friendly, Waterfront with Pier
Family and Pet-Friendly, Waterfront with Pier
10.0 out of 10, Exceptional, (262)
"This was an extension of our original 4-day stay. We had so much wonderful and fun time that we stayed an extra day. The owners Rob and Clarissa were the best host!"
United States
Alicia J.
Family and Pet-Friendly, Waterfront with Pier
Outdoor pool
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
9.8 out of 10, Exceptional, (7)
"Great House "
United States
Conrad L.
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
Smart TV, books, printers
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
9.4 out of 10, Exceptional, (20)
"This property is beautiful and perfect for large groups. There is plenty of room and very inviting. We had a great time!"
United States
Shannon T.
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Marina
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
9.6 out of 10, Exceptional, (17)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
United States
Aaron N.
The price is NZ$645
includes taxes & fees
27 Oct - 28 Oct
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Marina
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
10.0 out of 10, Exceptional, (95)
"Beautiful home in a quiet community. "
United States
Rebecca K.
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Terrace/patio
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
9.8 out of 10, Exceptional, (132)
"Great location with lots of privacy. The dock and the kayaks were a great hit with the family. Really no need to go anywhere. The house was really nice and very spacious. Some of the amenities like the grill and kitchen supplies could use some updating. A nice place to unwind with family and friends."
United States
Lisa T.
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Fridge, microwave, oven, stovetop
"Belle Aire Landing" a Large Beautiful Waterfront Estate! Under New Management!
"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"
United States
kathleen l.
"Belle Aire Landing" a Large Beautiful Waterfront Estate! Under New Management!
Private kitchen
Sailwinds Loft at Cambridge Creek
Sailwinds Loft at Cambridge Creek
9.8 out of 10, Exceptional, (18)
"The location and apartment were perfect. "
United States
Christina B.
The price is NZ$442
includes taxes & fees
27 Oct - 28 Oct
Sailwinds Loft at Cambridge Creek
Marina
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
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!"
United States
Angie R.
The price is NZ$514
includes taxes & fees
26 Oct - 27 Oct
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Interior
Thorneton Point Estate
Thorneton Point Estate
9.6 out of 10, Exceptional, (20)
"Beautiful, well-maintained property in a gorgeous waterside setting. "
United States
Peter S.
Thorneton Point Estate
Outdoor pool
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
10.0 out of 10, Exceptional, (137)
"Great home! Has everything you need, especially if you're traveling with children. Will def consider staying here again if we're in the area!"
United States
Ajiab R.
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Fridge, microwave, oven, stovetop
Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)
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!"
United States
Christine P.
Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)
Dining
Short drive to Downtown Cambridge | Private Dock | Pool | 16.5 Acres | Guest Hou
Short drive to Downtown Cambridge | Private Dock | Pool | 16.5 Acres | Guest Hou
9.2 out of 10, Wonderful, (5)
"Great stay"
United States
Jovan J.
Short drive to Downtown Cambridge | Private Dock | Pool | 16.5 Acres | Guest Hou
Interior
Warwick Farms Waterfront Retreat! Solitude and relaxation on the Warwick River
Warwick Farms Waterfront Retreat! Solitude and relaxation on the Warwick River
10.0 out of 10, Exceptional, (14)
"Great House, perfect for a group retreat in a peaceful location. The pool is fantastic on a hot day and the house has good AC to keep you cool.Would happily stay again"
United States
Ed L.
Warwick Farms Waterfront Retreat! Solitude and relaxation on the Warwick River
Fridge, microwave, oven, stovetop
Amazing views waterfront 3-bedroom home in Madison
Amazing views waterfront 3-bedroom home in Madison
9.8 out of 10, Exceptional, (6)
"the place was great. easy access to water and toys."
United States
Allen C.
Amazing views waterfront 3-bedroom home in Madison
Apartment (1 Bedroom) | Interior
Cambridge Apt in Walkable Neighborhood
Cambridge Apt in Walkable Neighborhood
3.0 star property
Cambridge Apt in Walkable Neighborhood
Fridge, microwave, oven, stovetop
Waterfront Getaway with Dock
Waterfront Getaway with Dock
10.0 out of 10, Exceptional, (51)
"Really neat property with everything that you need!"
United States
Hannah K.
The price is NZ$485
includes taxes & fees
16 Nov - 17 Nov
Waterfront Getaway with 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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Top Secretary Hotel Reviews

Hummingbird Inn

Hummingbird Inn

10/10 Excellent
"Our 2nd time here to spend our Anniversary. Lovely locale. Eric is a wonderful host and marvelous chef. We're thinkimg of returing for a 3rd visit next October. Birdie is a treasure too. All Inns should have dogs! :-)"
Brenda 1-night trip
Posted 1 day ago
Hummingbird Inn

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, 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 NZ$442 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?

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock: This holiday home rental outside of Secretary is located on the beach, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

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.