Book Holiday Homes in Secretary

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Featured Holiday Homes in Secretary

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge MD
The price is AU$518 per night from 5 Jan to 6 Jan
AU$518
5 Jan - 6 Jan 2026
includes taxes & fees
A stay at this vacation home places you in the heart of Cambridge, steps from Long Wharf Park and Choptank River Lighthouse.
Opens in a new windowCozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

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

Cambridge MD
Located in Cambridge, this vacation home is on the waterfront, within a 15-minute drive of Spocott Windmill and Richardson Maritime Museum.
Opens in a new windowNEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford MD
Located in Woolford, this vacation home is in a rural location, within a 10-minute drive of Blackwater National Wildlife Refuge and Harriet Tubman Underground ...
Opens in a new windowThe Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
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Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.

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

Easton MD
With a stay at this vacation home in Easton, you'll be on the beach, and 6.6 mi (10.7 km) from Saint Michaels Village and 7.3 mi (11.7 km) from St. Michaels ...
Opens in a new windowWoodwind Manor on the Tred Avon minutes to St Michaels and Easton.
 Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

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

Woolford MD
A stay at this vacation home places you in the heart of Woolford, and within a 15-minute drive of Blackwater National Wildlife Refuge.
Opens in a new window Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Cambridge MD
With a stay at this vacation home in Cambridge, you'll be on the waterfront, and 6.1 mi (9.9 km) from Christ Rock Park and 6.5 mi (10.5 km) from Snows Turn ...
Opens in a new windowYear Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28
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

Cambridge MD
Located in Cambridge, this vacation home is on the waterfront, within a 15-minute drive of Spocott Windmill and Chesapeake Bay.
Opens in a new windowWaterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Chesapeake Bay Large Beautiful Waterfront Estate! "Belle Aire Landing"

Chesapeake Bay Large Beautiful Waterfront Estate! "Belle Aire Landing"

3 out of 5
East New Market MD
Located in East New Market, this vacation home is on the waterfront, within a 15-minute drive of Bay Country Shop and Meredith House.
Opens in a new windowChesapeake Bay Large Beautiful Waterfront Estate! "Belle Aire Landing"
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

Cambridge MD
When you stay at this vacation home in Cambridge, you'll be on the waterfront and 15 minutes by car from Spocott Windmill.
Opens in a new windowShort drive to Downtown Cambridge | Private Dock | Pool | 16.5 Acres | Guest Hou
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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.

Secretary Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Secretary vacation homes are the perfect way for you to wing it.

Holiday houses in Secretary let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Secretary in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Secretary adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Secretary with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Secretary vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Secretary Holiday Homes essential information

Accommodation
131 Holiday Homes
Lowest Price
AU$139
Highest Price
AU$518
Popular accommodation
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina, NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock, The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks, Woodwind Manor on the Tred Avon minutes to St Michaels and Easton., Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock, Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28, Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW, Chesapeake Bay Large Beautiful Waterfront Estate! "Belle Aire Landing", Short drive to Downtown Cambridge | Private Dock | Pool | 16.5 Acres | Guest Hou

Top trending hotels in Secretary

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd Cambridge MD
Fully refundableReserve now, pay when you stay
The price is AU$334 per night from 1 Jan to 2 Jan
AU$334
1 Jan - 2 Jan 2026
includes taxes & fees
Located in Cambridge, Hyatt Regency Chesapeake Bay is on the waterfront, a 4-minute drive from Bay Country Shop and 5 minutes from Meredith House.
Opens in a new windowHyatt Regency Chesapeake Bay
Quality Inn

Quality Inn

2.5 out of 5
8523 Ocean Gtwy Easton MD
Fully refundableReserve now, pay when you stay
The price is AU$139 per night from 4 Jan to 5 Jan
AU$139
4 Jan - 5 Jan 2026
includes taxes & fees
A stay at Quality Inn places you in the heart of Easton, within a 15-minute walk of Talbot Massage and Easton Cycle and Sport.
Opens in a new windowQuality Inn
The Tidewater Inn

The Tidewater Inn

3 out of 5
101 E Dover St Easton MD
Fully refundableReserve now, pay when you stay
The price is AU$294 per night from 1 Jan to 2 Jan
AU$294
1 Jan - 2 Jan 2026
includes taxes & fees
When you a stay at The Tidewater Inn in Easton, you'll be in the historical district, within a 5-minute walk of Avalon Theatre and Talbot County Visitor ...
Opens in a new windowThe Tidewater Inn
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Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites

2.5 out of 5
8708 Alicia Drive Easton MD
Fully refundableReserve now, pay when you stay
The price is AU$195 per night from 25 Dec to 26 Dec
AU$195
25 Dec - 26 Dec
includes taxes & fees
With a stay at Best Western Plus Easton Inn & Suites in Easton, you'll be within a 5-minute drive of Easton Cycle and Sport and Talbot Massage.
Opens in a new windowBest Western Plus Easton Inn & Suites
Don't see what you're looking for?
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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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^Subject to availability and chosen travel dates.