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 NZ$584 per night from 5 Jan to 6 Jan
NZ$584
5 Jan - 6 Jan 2026
includes taxes & fees
Stay at this holiday home in Cambridge. Enjoy free Wi-Fi, breakfast (surcharge) and a garden. Popular attractions Choptank River Lighthouse and Long Wharf Park ...
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
Stay at this holiday home in Cambridge. Enjoy free Wi-Fi, private pools and a garden. Popular attractions Spocott Windmill and Brannock Maritime Museum are located ...
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
Stay at this holiday home in Woolford. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Woods Island and Harriet Tubman Underground Railroad ...
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
Stay at this beach holiday home in Easton. Enjoy free Wi-Fi, private pools and a beach locale. Popular attractions Oxford Museum and Royston Island are located ...
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
Stay at this beach holiday home in Woolford. Enjoy free Wi-Fi, private pools and a beach locale. Popular attractions Ragged Island and Spocott Windmill are located ...
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
Stay at this family-friendly holiday home in Cambridge. Enjoy free Wi-Fi, private pools and laundry facilities. Popular attractions Spocott Windmill and Ragged ...
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
Stay at this holiday home in Cambridge. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Ragged Island and Spocott Windmill are located ...
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
Stay at this beach holiday home in East New Market. Enjoy free Wi-Fi, private pools and a beach locale. Popular attractions Bill Burton Fishing Pier State Park ...
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
Stay at this family-friendly holiday home in Cambridge. Enjoy free Wi-Fi, private pools and a garden. Popular attractions Ragged Island and 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
NZ$160
Highest Price
NZ$584
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 NZ$383 per night from 1 Jan to 2 Jan
NZ$383
1 Jan - 2 Jan 2026
includes taxes & fees
Stay at this beach resort in Cambridge. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Our guests praise the pool and the helpful staff in their reviews. ...
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 NZ$160 per night from 30 Dec to 31 Dec
NZ$160
30 Dec - 31 Dec
includes taxes & fees
Stay at this business-friendly hotel in Easton. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms in ...
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 NZ$337 per night from 1 Jan to 2 Jan
NZ$337
1 Jan - 2 Jan 2026
includes taxes & fees
Stay at this spa hotel in Easton. Enjoy free Wi-Fi, free parking and a full-service spa. Our guests praise the helpful staff in their reviews. Popular attractions ...
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 NZ$224 per night from 25 Dec to 26 Dec
NZ$224
25 Dec - 26 Dec
includes taxes & fees
Stay at this business-friendly hotel in Easton. Enjoy free Wi-Fi, free parking and a fitness centre. Our guests praise the breakfast and the helpful staff in ...
Opens in a new windowBest Western Plus Easton Inn & Suites
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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.