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Secretary Vacation Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Secretary vacation rentals

A living room with two grey sofas, a coffee table, and a ceiling fan.

1. Cambridge Apt in Walkable Neighborhood

Cambridge Apt in Walkable Neighborhood
3.0 star property
Cambridge
10.0 out of 10, Exceptional, (1 review)
"This apt was built in the 50’s, or back when fewer outlets were needed, and it has window air conditioners. It was just what we were looking for as we visited the ste for family reunions"
United States
LOIS
The price is AED 349
AED 1,185 total
includes taxes & fees
15 Nov - 16 Nov
Cambridge Apt in Walkable Neighborhood
A living room with two grey sofas, a coffee table, and a ceiling fan.

2. Cambridge Apt in Walkable Neighborhood

Cambridge Apt in Walkable Neighborhood
Cambridge
8.0 out of 10, Very good, (4 reviews)
"great location."
United States
Anonymous traveler
The price is AED 242
AED 1,146 total
includes taxes & fees
15 Nov - 16 Nov
Cambridge Apt in Walkable Neighborhood
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

3. Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.4 out of 10, Exceptional, (26 reviews)
"Pet friendly!"
United States
Mary Beth S.
The price is AED 624
AED 1,355 total
includes taxes & fees
15 Dec - 16 Dec
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
A modern kitchen with white cabinets, a stainless steel stove, a microwave, and a sink.

4. Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (40 reviews)
"Wonderful place to stay."
United States
Sharon D.
The price is AED 569
AED 888 total
includes taxes & fees
16 Nov - 17 Nov
Sailwinds Loft at Cambridge Creek
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

5. The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Downtown Cambridge
9.8 out of 10, Exceptional, (15 reviews)
"Great stay! Gorgeous apartment!"
United States
Kristen S.
The price is AED 624
AED 1,343 total
includes taxes & fees
15 Dec - 16 Dec
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
A wooden interior with a dining area, sofas, and a table.

6. WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Cambridge
9.0 out of 10, Wonderful, (16 reviews)
"Very spacious home. 4 bedrooms and 4 baths. Great basement for watching TV with a large group. Home is about 15 minutes from downtown Cambridge."
United States
Anonymous traveler
The price is AED 814
AED 1,599 total
includes taxes & fees
15 Nov - 16 Nov
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
A marina with boats docked, a water tower, and residential buildings with balconies.

7. Marina Views | 3BR Downtown Townhouse, Heated Decks, Pool & Gym

Marina Views | 3BR Downtown Townhouse, Heated Decks, Pool & Gym
Cambridge
10.0 out of 10, Exceptional, (2 reviews)
"We only stayed one night but wouldn't hesitate to come back and stay for a few days. Beautiful home overlooking the docks."
United States
mike
The price is AED 773
AED 2,069 total
includes taxes & fees
15 Nov - 16 Nov
Marina Views | 3BR Downtown Townhouse, Heated Decks, Pool & Gym
A dining area with a round table, chairs, and a decorative table runner.

8. More, than just a place to sleep - welcome home!

More, than just a place to sleep - welcome home!
Cambridge
The price is AED 1,095
AED 1,420 total
includes taxes & fees
15 Nov - 16 Nov
More, than just a place to sleep - welcome home!
A rustic cabin with a sign reading 'A-M-A-L-G-A-M-A-T-E-D' and a small outdoor seating area with two chairs.

9. Cozy County Autumn Escape at the Millpond Cottage - Pet Friendly!

Cozy County Autumn Escape at the Millpond Cottage - Pet Friendly!
Seaford
10.0 out of 10, Exceptional, (1 review)
"This was a clean, comfortable place to stay. We only stayed one night, but would've enjoyed staying longer. Sitting outside with coffee in the morning was special. The number of different birds we heard was amazing. We didn't have time to explore the pond, but it added to a nice, quiet stay."
United States
Whitney H.
The price is AED 397
AED 569 total
includes taxes & fees
22 Nov - 23 Nov
Cozy County Autumn Escape at the Millpond Cottage - Pet Friendly!
Living area

10. EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places

EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places
Easton
10.0 out of 10, Exceptional, (1 review)
"Fabulous location in town location! It was much larger than we expected - 2 levels. Nice open layout on the main level with 2 BR/BA and a 3rd BR/BA on 2nd floor. Owners are very responsive before and during the trip. We could not connect to the TV, but owner quickly offered assistance. Bathrooms can use some towel racks and shelves. Beds/pillows were comfy! We were very happy with our stay."
United States
Lynn G.
The price is AED 826
AED 1,479 total
includes taxes & fees
18 Nov - 19 Nov
EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places
A kitchen with white cabinets, a stainless steel refrigerator, a microwave, a stove, and a sink.

11. Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (69 reviews)
"Excellent stay! Just as described! Very quiet, private location."
United States
Mills Family A.
The price is AED 900
AED 1,036 total
includes taxes & fees
15 Nov - 16 Nov
Waterfront Getaway with Dock
A lakeside view from a deck with a wooden railing, a sandy area with a boat, and a dock extending into the water.

12. 2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.

2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.
Cambridge
The price is AED 826
AED 954 total
includes taxes & fees
15 Nov - 16 Nov
2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

13. WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (17 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is AED 1,053
AED 1,844 total
includes taxes & fees
19 Nov - 20 Nov
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
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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Top Secretary Hotel Reviews

Sandaway Suites & Beach

Sandaway Suites & Beach

10/10 Excellent
"We stay at Sandaway every year for the St. Michael's Oyster Fest, and it's one of the most relaxing places my wife and I stay (and we travel quite a lot!) The beds are great, the views are unbeatable, and the staff is incredibly accommodating. We can't wait for our next stay here next year!"
Philip 2-night trip
Posted 5 days ago
Sandaway Suites & Beach

Frequently asked questions

Are there vacation rentals in Secretary?

Yes, there are vacation rentals near well known local attractions in Secretary, or you can go with a secluded option if you'd like a relaxing place to stay.

What's the top vacation rental in Secretary?

Private 2 Acre Waterfront Family Retreat with Pool & Pier: Visitors like this Secretary vacation home rental. It is located on the waterfront and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of books.

What’s there to see and do in Secretary?

While exploring the area, visit family-friendly sights like Bay Country Shop, or get outside and enjoy nature at Long Wharf Park. In the larger area, you’ll find Dorchester County Visitors Center and Choptank River Lighthouse.

What’s a vacation rental in Secretary like?

Vacation rentals are private properties you can book for short or long periods in Secretary. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll feel right at home. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from public hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for families.