Book Holiday Homes in Secretary

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Featured Holiday Homes in Secretary

Private 2 Acre Waterfront Family Retreat with Pool & Pier

Private 2 Acre Waterfront Family Retreat with Pool & Pier

Cambridge MD
When you stay at this vacation home in Cambridge, you'll be on the waterfront and 14 minutes by car from Christ Rock Park.
Opens in a new windowPrivate 2 Acre Waterfront Family Retreat with Pool & Pier
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

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

Easton MD
When you stay at this vacation home in Easton, you'll be on the waterfront and 14 minutes by car from Hog Neck Golf Course.
Opens in a new windowBeautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Amazing views waterfront 3-bedroom home in Madison with a 190 foot pier!

Amazing views waterfront 3-bedroom home in Madison with a 190 foot pier!

Madison MD
Located in Madison, this vacation home is on the waterfront, within a 15-minute drive of Blackwater National Wildlife Refuge and Harriet Tubman Underground Railroad ...
Opens in a new windowAmazing views waterfront 3-bedroom home in Madison with a 190 foot pier!
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Historic Waterfront Estate with Pool & Pet-Friendly  – Perfect for Fall Getaways

Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways

Oxford MD
Located in Oxford, this vacation home is on the waterfront, within a 10-minute drive of Play Ball Dog Park and Oxford Museum.
Opens in a new windowHistoric Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways
Thorneton Point Estate

Thorneton Point Estate

Easton MD
Located in Easton, this vacation home is on the waterfront, within a 10-minute drive of Saint Michaels Village and St. Michaels Winery.
Opens in a new windowThorneton Point Estate
Stylish Home on the Choptank River (with Tidal Beach)

Stylish Home on the Choptank River (with Tidal Beach)

Preston MD
Located in Preston, this vacation home is by the sea, within a 15-minute drive of Gilpin's Point Landing and Williston Lake.
Opens in a new windowStylish Home on the Choptank River (with Tidal Beach)
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

Easton MD
With a stay at this vacation home in Easton, you'll be on the beach, and 6.7 mi (10.7 km) from Avalon Theatre and 6.7 mi (10.7 km) from Talbot County Visitor ...
Opens in a new windowModern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
"Endless Summer" Waterfront on the Chesapeake Bay!

"Endless Summer" Waterfront on the Chesapeake Bay!

Woolford MD
When you stay at this vacation home in Woolford, you'll be 14 minutes by car from Blackwater National Wildlife Refuge.
Opens in a new window"Endless Summer" Waterfront on the Chesapeake Bay!
Waterfront home with private dock near St. Michaels & Easton

Waterfront home with private dock near St. Michaels & Easton

Easton MD
Located in Easton, this vacation home is on the waterfront, a 5-minute drive from Saint Michaels Village and 6 minutes from St. Michaels Winery.
Opens in a new windowWaterfront home with private dock near St. Michaels & Easton
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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
123 Holiday Homes
Lowest Price
AU$114
Highest Price
AU$430
Popular accommodation
Private 2 Acre Waterfront Family Retreat with Pool & Pier, Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac, Amazing views waterfront 3-bedroom home in Madison with a 190 foot pier!, Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways, Thorneton Point Estate, Stylish Home on the Choptank River (with Tidal Beach), Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks, "Endless Summer" Waterfront on the Chesapeake Bay!, Waterfront home with private dock near St. Michaels & Easton

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$430 per night from 16 Apr to 17 Apr
AU$430
16 Apr - 17 Apr
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
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
The price is AU$215 per night from 5 Apr to 6 Apr
AU$215
5 Apr - 6 Apr
includes taxes & fees
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
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$268 per night from 5 Apr to 6 Apr
AU$268
5 Apr - 6 Apr
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
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Days Inn & Suites by Wyndham Cambridge

Days Inn & Suites by Wyndham Cambridge

2.5 out of 5
2917 Ocean Gateway Cambridge MD
Fully refundableReserve now, pay when you stay
The price is AU$114 per night from 5 Apr to 6 Apr
AU$114
5 Apr - 6 Apr
includes taxes & fees
When you stay at Days Inn & Suites by Wyndham Cambridge in Cambridge, you'll be near the beach, within a 5-minute drive of Bay Country Shop and Meredith ...
Opens in a new windowDays Inn & Suites by Wyndham Cambridge
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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.