Secretary Vacation Rentals

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Vacation Rentals in Secretary

Fridge, microwave, oven, stovetop
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (16)
"The Hudson House was perfect for our stay. My boys were in awe of the house. The owners have made it so cozy and have paid such close attention to details. There were snacks, amazing notes to help you navigate the house, and games to keep the kids busy. I highly recommend this to anyone looking to have a relaxing weekend right on the water. -Nicole M."
The price is $264
$470 total
includes taxes & fees
May 21 - May 22
Beautiful Waterfront Retreat in Cambridge!
Fridge, microwave, oven, stovetop
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
10.0 out of 10, Exceptional, (30)
"Great place to recharge for a few days as a family! Beautiful and peaceful in the fall — though my kids are ready to come back and use the pool in warmer weather!!!"
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
Property grounds
Modern Country Home with Pool and Game Room
10.0 out of 10, Exceptional, (1)
"Nice place. Well accommodated."
Modern Country Home with Pool and Game Room
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Property grounds
St. Michaels Waterfront Home
10.0 out of 10, Exceptional, (20)
"Beautiful house, perfect for a weekend getaway with young kids. The host was very helpful!"
St. Michaels Waterfront Home
Fridge, microwave, oven, stovetop
Waterfront Getaway with Dock
10.0 out of 10, Exceptional, (25)
"We loved the proterty! House was set up with pleanty of room for 4 of us. It was clean and comfortable. Out back was very private. Would definitely stay here again. We had a blast!"
The price is $220
$262 total
includes taxes & fees
May 20 - May 21
Waterfront Getaway with Dock
Pool
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
10.0 out of 10, Exceptional, (1)
"This was the most peaceful and perfect property. I felt like I was on vacation and able to relax! We would definitely return if we are in the area again."
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
TV, fireplace, books
Cambridge Beach Home on Choptank River w/ Pier!
10.0 out of 10, Exceptional, (11)
"We are a group of mid 50s ladies that went to Jr High and High School together. We do an annual "girls" trip and usually head to Deep Creek Lake or Ocean City where some of us own second homes. We decided to switch things up this year and found this amazing rental. From the moment we walked in the door and saw the lovely note and goodies that were left for us - to the beautiful decor and gorgeous bedrooms. There was absolutely nothing missed in this rental. Kitchen fully stocked AND MORE!!! The...
Cambridge Beach Home on Choptank River w/ Pier!
Beach/ocean view
Luxury Waterfront Retreat with in ground pool and close to town
10.0 out of 10, Exceptional, (24)
"We stayed here as two families for thanksgiving. The kids (ages 6-15) loved the upstairs. So cozy and the game room was great for family movie night. The kitchen was perfect for all of our cooking. Lots of counter space, drink fridge really helped give extra space in main fridge, kitchen is very well stocked with pots, bakeware, crockpot, blender, and plenty of dinnerware/silverware. The backyard, dock, patio, and awesome view of the sunsets was our afternoon/evening entertainment. We went into...
Luxury Waterfront Retreat with in ground pool and close to town
Sun loungers, beach towels
Cottage at Goose Neck Point
10.0 out of 10, Exceptional, (20)
"We have been VRBO'ing for quite a few years now and have had lots of positive experiences - but THIS property goes beyond all expectations in ways others can't. I can't think of another property layout that could offer what this one does - soothing water in every direction (where else can you see sunrise AND sunset over water?) and the large screened in porch with a view of the water was so comfortable and relaxing that we had to talk ourselves into leaving to go anywhere! The host could not...
Cottage at Goose Neck Point
Outdoor pool
New St. Michaels estate -Pier,Pool, Gas fire pit, Bikes & Kayaks.
10.0 out of 10, Exceptional, (126)
"While we wished for weather that was slightly better, we still enjoyed every minute of our 3 days. The weather didn't stop us from using the Kayaks or trying to catch a crab or two. the yard was perfect for exercising the kids and the puppies. It was a short easy drive into town, for some shopping, eating and even a visit to a rum distillery. The wineries were all closed at the beginning of the week this time of year. The house was supplied with everything we needed. The listing was spot on,...
New St. Michaels estate -Pier,Pool, Gas fire pit, Bikes & Kayaks.
Property grounds
Minutes from Downtown Easton and St. Michaels | Charming | 4000 ft of Shoreline
10.0 out of 10, Exceptional, (3)
"All day views. Sunrises and sunsets. Quiet and easy to get to. Beautiful property and the house is perfect for a small group. Dock is great for crabbing and fishing. Will be back for sure!"
Minutes from Downtown Easton and St. Michaels | Charming | 4000 ft of Shoreline
Property grounds
Spacious waterfront home with amazing views, private pier, fishing and crabbing.
10.0 out of 10, Exceptional, (17)
"This is a lovely home with beautiful water views. There was more than enough space for the 9 of us. We would definitely stay here again!"
Spacious waterfront home with amazing views, private pier, fishing and crabbing.
Smart TV
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
10.0 out of 10, Exceptional, (8)
"We had a wonderful time! The house was super cute and clean. The views off the water in the morning and the evening were beautiful! All of the blackout shades came in very handy for our baby and little ones who sleep better in darker rooms. The hot tub was magical and taking the kayaks out onto the water was so fun! Only recommendation would be to bring bug spray! Thanks for a wonderful stay. We would love to come back."
The price is $300
$577 total
includes taxes & fees
May 22 - May 23
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Smart TV, books, printers
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
10.0 out of 10, Exceptional, (5)
"We had a lovely stay at The Blue Heron. We had a retreat scheduled with friends that we had to relocate last minute due to snow in western Maryland. We stumbled upon this listing, and the home was perfect for our needs. Plenty of beds, fully stocked kitchen, several rooms and couches for those who wanted to read, others to play games, and others to watch football playoffs on tv. The best part of the house was the dining room table that could seat up to 18 (?). It was nice to be able to not have...
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Property grounds
Private 9 acre Family Retreat on the Chesapeake Bay
10.0 out of 10, Exceptional, (4)
"We came together, 3 generations, to celebrate a birthday The house easily accommodated all of us, our 2 sons with their wives, children (2 each), and ourselves. We had plenty of space to find solitude and to be together. The extra large and spacious deck and generous living space made being together indoors and outside easy. The house is super well equipped for family visits with kids. Plenty of games and toys for kids of all ages. Kate was extremely responsive and welcoming. from the...
Private 9 acre Family Retreat on the Chesapeake Bay
Interior
Cottage on Cabin Creek
10.0 out of 10, Exceptional, (91)
"Beautiful views of the water and very quiet. The kayaks are a great added touch"
The price is $250
$364 total
includes taxes & fees
May 31 - Jun 1
Cottage on Cabin Creek
Property grounds
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
10.0 out of 10, Exceptional, (21)
"Perfect for a group gathering! Incredible views."
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
Property grounds
Sunset Breezes - quiet waterfront retreat
10.0 out of 10, Exceptional, (32)
"We had two families get away for my wife’s birthday. Four adults and three kids. The rooms were perfect sizes for our group. The kitchen was very well stocked for the various meals we prepared. The grounds were just perfect especially if you want a peaceful water setting to look at each day. The only possible complaint we had was the fact that the listing claimed there was a hot tub present, which was not the case. Otherwise, we’d definitely come back again!"
The price is $226
$279 total
includes taxes & fees
May 21 - May 22
Sunset Breezes - quiet waterfront retreat
Dining
Short drive to Downtown Cambridge | Private Dock | Kayaks | 16.5 Acres | Guest H
10.0 out of 10, Exceptional, (1)
"We have 4 adult children and their children who decided to plan a get away to help us celebrate. A location no one had ever been to and on the water. It is lovely and did meet all our needs. Biggest shock was jellyfish in the water but that is their home. Sliding door from the dining room out onto the porch is difficult to open. Another great addition would be a step from the bedroom to the porch. The family just wanted to spend time together and this rental is perfect. We smiled as grandsons...
Short drive to Downtown Cambridge | Private Dock | Kayaks | 16.5 Acres | Guest H
Fridge, microwave, oven, stovetop
Thorneton Point Estate
9.8 out of 10, Exceptional, (6)
"We had a great time. The pool was a big hit and all the common areas in the house gave us plenty of room to spread out. The game room was super, also. A few things that would make it even greater: about half a dozen cockroaches and other bugs were found in the house; lack of instruction manuals for appliances and sauna; exterior doors very difficult to lack; comforter in bedroom 1 smelled like dogs. Matt was very helpful and responsive to questions"
Thorneton Point Estate
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See all available properties in Secretary
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.

Other types of properties in Secretary you may be interested in

Exterior
Best Western Plus Easton Inn & Suites
2.5 star property
9.4 out of 10, Exceptional, (1001)
"We've stayed here before and will stay again, anytime we're in Easton. The hotel is easy to find, comfortable, well kept and the staff are always pleasant."
The price is $129
$142 total
includes taxes & fees
May 19 - May 20
Best Western Plus Easton Inn & Suites
Indoor pool, 2 outdoor pools, pool umbrellas, sun loungers
Hyatt Regency Chesapeake Bay
4.0 star property
8.8 out of 10, Excellent, (1002)
"I thought the dog friendly environment was a good option."
The price is $179
$245 total
includes taxes & fees
May 22 - May 23
Hyatt Regency Chesapeake Bay
Front of property
St Michaels Inn
2.5 star property
8.2 out of 10, Very Good, (1000)
"The staff was frieendly and very helpful, and the motel was very nice. The only issue I had with the stay was the high sulfur content of the water. It stank, and that's quite unpleasant."
The price is $127
$140 total
includes taxes & fees
May 19 - May 20
St Michaels Inn
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.

Everything you need to know about Secretary vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Secretary vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Secretary vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Secretary vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Secretary. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Secretary in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $175 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Secretary rentals

At Expedia, we put the best Secretary vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Secretary rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Secretary vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Secretary. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Beautiful Waterfront Retreat in Cambridge!: You might want to consider this vacation rental near Secretary, which is located on the waterfront and has a selection of games, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals will I find in Secretary?

With 5 Expedia vacation rentals, you're sure to find just the right place for your Secretary stay.

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.

Recent reviews of Secretary properties
Expedia verified reviews

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

5/5 Excellent
"Place was lovely but the concierge did not kno hownto do there job...They kept trying to over charge me"
A verified traveler stayed at Hyatt Regency Chesapeake Bay
Posted 3 days ago
Hyatt Regency Chesapeake Bay