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$506 per night from 16 Feb to 17 Feb
AU$506
16 Feb - 17 Feb
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
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
"Belle Aire Landing" a Large Beautiful Waterfront Estate! Under New Management!

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

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 window"Belle Aire Landing" a Large Beautiful Waterfront Estate! Under New Management!
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
St. Michaels Waterfront Home

St. Michaels Waterfront Home

New comb MD
Located in Easton, this vacation home is on the waterfront, a 4-minute drive from Saint Michaels Village and 5 minutes from St. Michaels Winery.
Opens in a new windowSt. Michaels Waterfront Home
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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$185
Highest Price
AU$506
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, Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW, "Belle Aire Landing" a Large Beautiful Waterfront Estate! Under New Management!, Short drive to Downtown Cambridge | Private Dock | Pool | 16.5 Acres | Guest Hou, St. Michaels Waterfront Home

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$339 per night from 22 Feb to 23 Feb
AU$339
22 Feb - 23 Feb
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 Eastern Shore Hospital ...
Opens in a new windowHyatt Regency Chesapeake Bay
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$278 per night from 25 Feb to 26 Feb
AU$278
25 Feb - 26 Feb
includes taxes & fees
When you stay at The Tidewater Inn in Easton, you'll be in the historical district, just steps from Avalon Theatre and Talbot County Visitor Center.
Opens in a new windowThe Tidewater Inn
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$185 per night from 16 Feb to 17 Feb
AU$185
16 Feb - 17 Feb
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
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St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street St. Michaels MD
Fully refundableReserve now, pay when you stay
When you stay at St Michaels Inn in St. Michaels, you'll be in the historical district, within a 5-minute drive of St. Michaels Winery and Chesapeake Bay Maritime ...
Opens in a new windowSt Michaels Inn
Don't see what you're looking for?
See all available properties in Secretary
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.