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
The price is AU$598 per night from 18 Nov to 19 Nov
AU$598
18 Nov - 19 Nov
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
Charming Waterfront Stay close to St. Michaels

Charming Waterfront Stay close to St. Michaels

Easton
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 windowCharming Waterfront Stay close to St. Michaels
Escape with family or friends to this peaceful, 4-bedroom retreat on the water

Escape with family or friends to this peaceful, 4-bedroom retreat on the water

2 out of 5
Cambridge
With a stay at this vacation home in Cambridge, you'll be within a 15-minute drive of Spocott Windmill and Richardson Maritime Museum.
Opens in a new windowEscape with family or friends to this peaceful, 4-bedroom retreat on the water
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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
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.
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
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
RANCH AT ROYAL OAK- Exclusive waterfront pool pier

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

Royal Oak
With a stay at this vacation home in Royal Oak, you'll be on the waterfront, and 7.8 mi (12.6 km) from Saint Michaels Village and 8.3 mi (13.3 km) from St. Michaels ...
Opens in a new windowRANCH AT ROYAL OAK- Exclusive waterfront pool pier
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
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
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford
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
Waterfront Getaway with Dock

Waterfront Getaway with Dock

Woolford
The price is AU$415 per night from 4 Nov to 5 Nov
AU$415
4 Nov - 5 Nov
includes taxes & fees
Located in Woolford, this vacation home is on the waterfront, within a 10-minute drive of Blackwater National Wildlife Refuge and Harriet Tubman Underground ...
Opens in a new windowWaterfront Getaway with Dock
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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$169
Highest Price
AU$598
Popular accommodation
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina, Charming Waterfront Stay close to St. Michaels, Escape with family or friends to this peaceful, 4-bedroom retreat on the water, Woodwind Manor on the Tred Avon minutes to St Michaels and Easton., Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW, RANCH AT ROYAL OAK- Exclusive waterfront pool pier, Short drive to Downtown Cambridge | Private Dock | Pool | 16.5 Acres | Guest Hou, The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks, Waterfront Getaway with Dock

Top trending hotels in Secretary

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd, Cambridge, MD
The price is AU$320 per night from 23 Nov to 24 Nov
AU$320
23 Nov - 24 Nov
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
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
Fully refundable
The price is AU$169 per night from 6 Nov to 7 Nov
AU$169
6 Nov - 7 Nov
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
The price is AU$301 per night from 4 Nov to 5 Nov
AU$301
4 Nov - 5 Nov
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
Save an average of 15% on thousands of hotels when you're signed in
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$200 per night from 9 Nov to 10 Nov
AU$200
9 Nov - 10 Nov
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?
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.