Secretary Vacation Rentals

Vacation Rentals in Secretary

Waterfront property with private boat ramp and new dock!
Outdoor dining
Waterfront property with private boat ramp and new dock!
Waterfront property with private boat ramp and new dock!
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Fridge, microwave, stovetop, dishwasher
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, 4 reviews
"We extremely enjoyed our stay. The house was beautiful, kitchen was well equipped and the view was spectacular, especially with the Eagles that have nested on the 32 acre property. However was disappointed in the fact that the fire places were not in working conditions and rooms should have been number. We enjoy kayaking up and down the bay and taking it all in. I would definitely stay again."
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Cottage at Goose Neck Point
Sun loungers, beach towels
Cottage at Goose Neck Point
10.0 out of 10, Exceptional, 22 reviews
"My husband and I were looking for a place to getaway for the weekend, on the water. We found this adorable cottage, right on the water and close to Saint Michaels. We have been down to the area several times and really this was one of the best stays. The Hosts were really great, left us a bottle of wine and cheese plate when we arrived! the only thing that would have improved our stay would be if the bed was a little more comfortable. (by no means does this take away from the overall experience)...
Cottage at Goose Neck Point
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Beautiful Waterfront Retreat in Cambridge!
Fridge, microwave, oven, stovetop
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, 16 reviews
"We had a very enjoyable and relaxing stay here for Mother's Day weekend, coming in from DC. The property is in a great spot on the water and is a short ride into town. The house itself is cozy, clean, and welcoming with everything you need (including the crab house out back, which our four year old loved!) Rebecca is a thoughtful and accommodating host, too. She gave us several recommendations for food in the area and we really enjoyed her suggested restaurants in Cambridge and in Easton on the...
The price is $292
$506 total
includes taxes & fees
Jun 16 - Jun 17
Beautiful Waterfront Retreat in Cambridge!
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
Fridge, microwave, oven, stovetop
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
10.0 out of 10, Exceptional, 31 reviews
"One of the best properties I have stayed at. With all the amenities, you never need to leave the home. We enjoyed the views, the quietness of the area, and the wildlife. We nicknamed two beautiful ducks…Sonny and Cher! The house is very clean, the checkin checkout procedures were very easy. The host communicated all the details plus additional suggestions. We are definitely returning very soon."
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
Waterfront, Pool, Dock, Hot Tub.Stunning Views! A Luxury VIP Vacation Rental
Interior
Waterfront, Pool, Dock, Hot Tub.Stunning Views! A Luxury VIP Vacation Rental
9.2 out of 10, Wonderful, 15 reviews
"We were pleasantly surprised that the house is the end of the small road with several private acres. The layout offered main floor bed/bath for my parents, 2nd floor 3b/3b for my brother and his teens, and an attached garage apartment for my husband and I. The pool was fun and well kept. The dock was protected and allowed us to rent a boat and the guys to fish. The kitchen had everything a gourmet chef could imagine. Our main difficulty was that there was no easy place/way to launch kayaks or...
Waterfront, Pool, Dock, Hot Tub.Stunning Views! A Luxury VIP Vacation Rental
Downtown St. Michaels | Bikes | Kayaks | Private Pier
Beach
Downtown St. Michaels | Bikes | Kayaks | Private Pier
9.8 out of 10, Exceptional, 20 reviews
"Very clean and large property on scenic river. Only disappointing issues included problems launching kayaks over a tall wall and unfriendly TY cable system. Offset by abundance of great restaurants and peaceful and well maintained home."
Downtown St. Michaels | Bikes | Kayaks | Private Pier
Waterfront, cozy cottage with private pool on 27 acres of privacy
Beach nearby
Waterfront, cozy cottage with private pool on 27 acres of privacy
9.8 out of 10, Exceptional, 85 reviews
"We came for the Ironman 140.6 and we lucked out finding this lovely cottage! It was the perfect location, the property was beautful, and the house was very clean and had everything we needed. Dave and Cindy were so kind and helpful! They welcomed us to the property, gave us restaurant recommendations, let us pick some figs, and were very helpful when I left something behind. We would love to stay again!"
Waterfront, cozy cottage with private pool on 27 acres of privacy
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Smart TV, books, printers
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
10.0 out of 10, Exceptional, 5 reviews
"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
Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks
Fridge, microwave, oven, stovetop
Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks
9.6 out of 10, Exceptional, 4 reviews
"Nice place for a getaway."
The price is $450
$907 total
includes taxes & fees
Jun 9 - Jun 10
Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
Pool
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
10.0 out of 10, Exceptional, 1 review
"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
Thorneton Point Estate
Fridge, microwave, oven, stovetop
Thorneton Point Estate
9.8 out of 10, Exceptional, 6 reviews
"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
Warwick Farms Waterfront Retreat! Solitude and relaxation on the Warwick River
Interior
Warwick Farms Waterfront Retreat! Solitude and relaxation on the Warwick River
10.0 out of 10, Exceptional, 1 review
"Spacious quiet setting, enjoyed paddle board and kayaking on the river. Back country rd to take walks and large pool to keep cool."
Warwick Farms Waterfront Retreat! Solitude and relaxation on the Warwick River
Stylish Home on the Choptank River (with Tidal Beach)
Property grounds
Stylish Home on the Choptank River (with Tidal Beach)
10.0 out of 10, Exceptional, 25 reviews
"The home is clean, comfortable, and has a gorgeous outdoor living space right on the water. We even had my son's wedding day party prep photos taken here. We would definitely stay here again."
Stylish Home on the Choptank River (with Tidal Beach)
Cambridge Beach Home on Choptank River w/ Pier!
TV, fireplace, books
Cambridge Beach Home on Choptank River w/ Pier!
10.0 out of 10, Exceptional, 12 reviews
"This place was perfect for our group of 9. Super well equipped. There wasn't a single thing we needed that it didn't have. Lovely!"
Cambridge Beach Home on Choptank River w/ Pier!
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Property grounds
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Luxury Waterfront Retreat with in ground pool and close to town
Beach/ocean view
Luxury Waterfront Retreat with in ground pool and close to town
10.0 out of 10, Exceptional, 24 reviews
"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
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Lake
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
9.8 out of 10, Exceptional, 67 reviews
"Wonderful house. Well stocked with supplies. Great open floor plan along with a couple separate spaces on the main floor. Our group had 7 adults and our eight grandchildren six and under. Pool has gated access which was a key feature with all our little ones. The owner provided much info regarding things to do in the area. The bedroom spaces worked out great with our mix. We really enjoyed the crab traps and the dock for fishing. It was mostly casting practice but the kids loved it. We enjoyed...
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Amazing Waterfront Retreat On The Chesapeake Bay Private Pool Private Beach
Outdoor pool
Amazing Waterfront Retreat On The Chesapeake Bay Private Pool Private Beach
9.8 out of 10, Exceptional, 51 reviews
"We have enjoyed our stay at the property, everything was very nice and spacious away from everything, just the way we wanted. Our only issue was the landscaping work being done for 2 days of our stay, my son has allergies on cut grass and he ended up staying indoor for the most of those days."
Amazing Waterfront Retreat On The Chesapeake Bay Private Pool Private Beach
New St. Michaels estate -Pier,Pool, Gas fire pit, Bikes & Kayaks.
Outdoor pool
New St. Michaels estate -Pier,Pool, Gas fire pit, Bikes & Kayaks.
10.0 out of 10, Exceptional, 126 reviews
"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.
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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

Hyatt Regency Chesapeake Bay
Indoor pool, 2 outdoor pools, pool umbrellas, sun loungers
Hyatt Regency Chesapeake Bay
4.0 star property
8.8 out of 10, Excellent, 1,009 reviews
"The resort is great. Much to do on-site. My only complaint is that it is apparently a popular wedding venue so some areas were off limits, the restaurants crowded. "
The price is $206
$276 total
includes taxes & fees
Jun 11 - Jun 12
Hyatt Regency Chesapeake Bay
St Michaels Inn
Front of property
St Michaels Inn
2.5 star property
8.2 out of 10, Very Good, 1,004 reviews
"Toilet seat was pealing. Bathroom floor needed a scrub."
The price is $138
$151 total
includes taxes & fees
Jun 19 - Jun 20
St Michaels Inn
Best Western Plus Easton Inn & Suites
Exterior
Best Western Plus Easton Inn & Suites
2.5 star property
9.4 out of 10, Exceptional, 1,003 reviews
"First of all the people that work there were all friendly and very helpful. We were going to a wedding and I wish that the lighting in the room was better especially in the bathroom for putting on makeup. The sheets were a bit scratchy but overall the room was much bigger than we needed. Anything that we asked for was immediately brought for example towels."
The price is $139
$153 total
includes taxes & fees
Jun 10 - Jun 11
Best Western Plus Easton Inn & Suites
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 $292 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?

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!: You might want to consider this vacation home rental near Secretary, which is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 7 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 selection of games and a spa tub.

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

Holiday Inn Express Cambridge, an IHG Hotel

Holiday Inn Express Cambridge, an IHG Hotel

5/5 Excellent
"I did not like there was not an outdoor area to sit on a beautiful day; like maybe outside the indoor pool area where the grass is ; fence in and put tables, chairs some kind of seating. Place was great though!!! Beds so comfortable and staff very friendly!!! "
A verified traveler stayed at Holiday Inn Express Cambridge, an IHG Hotel
Posted 2 days ago
Holiday Inn Express Cambridge, an IHG Hotel