Mad Men Vacation Rentals

Our Properties

All our Mad Men Vacations properties have a mid century modern feel with a few signature features like a swing chair/chairs, a record player with blue tooth capability, outdoor string lights and a custom painted geometric wall design. 

This 3 bedroom, 2 full bath (one en suite) bay front home (sleeps 8) is only a 5-8 minute walk to the beach. It has a lovely covered deck that offers amazing bay views all year round. We provide two kayaks and our community has two pools, two tennis courts, shuffle board and mini golf in the summer. Popular Northside Park and numerous restaurants and bars are but a short walk away.

This 8 bedroom, 4.5 bath villa (sleeps 16) with a newly extended patio and renovated, screened-in salt water pool with in-ground Jacuzzi spa is only 6 miles from Walt Disney World and 17 miles from Universal Studios. The main living space has a “Disney Glam” theme and every bedroom has a decor based on the Magic Kingdom theme park.

This 6 bedroom, 4 full bath lakefront home (sleeps 14) is only 1.8 miles from Wisp Ski Resort. It features a modern but rustic vibe – all the bedrooms have a mountain-lake theme and it has a cool, retro game room with everything you want for endless hours of fun! Outside, enjoy beautiful lake views, your own dock for a boat, a hot tub, a fire pit, 2 Kayaks and a Canoe!  “The most unique vacation rental in Maryland” according to a popular travel blogger: https://www.onlyinyourstate.com/maryland/most-unique-airbnb-md/?fbclid=IwAR0XEds2KSKJnR_C2cwiuTQFY25UDmlaLe6wR_WaKdxKqrVtXvcgWCmfQbQ

Your Kissimmee Bucket List

Whether you are looking to escape the cold for a sunny holiday, are a Walt Disney World annual pass holder or taking the kids to meet Mickey for the first time Kissimmee, Florida is not only right next to Walt Disney World but also close to other fun amusements the area has to offer! Our bucket list guides will help you plan the perfect trip!

It doesn’t matter where you come from or how old you are, Walt Disney World has something for everyone! Check out this guide to see what not to miss when you visit!

Get your thrills on the cutting-edge rides, shows and attractions that bring your favorite movies, television and more to life at Universal Studios! This guide will give you a taste of all the fun to come!

Sea World is a wonderland of ocean animals, rides and dazzling shows! There is so much to do and this guide will give you all the details to help you plan your best trip there!

Your Deep Creek Bucket List

This four season resort town is only a few short hours drive from Washington DC, Baltimore, Philadelphia, Pittsburgh and New York and our bucket list guides will help you plan the perfect trip!

The lake! Need I say more? Deep Creek Lake covers approximately 3,900 acres and has 69 miles of shoreline for endless hours of fun and adventure in the spring, summer and fall! This guide gives you all details you need to know!

Every season in Deep Creek offers a different lens to the see the beauty of nature. Whether you want a short easy hike or a more advanced hiking adventure this guide will help you plan what is right for you!

Maryland’s only downhill ski resort is the perfect activity for you best winter getaway. This guide gives you all you need to know to plan your ski  or snowboard trip vacation!

Your Ocean City Bucket List

If you are in search of the best vacation town with pristine beaches, endless fun exploring the bay and an iconic, award-winning boardwalk with endless amusements, our bucket list guides will help you plan the perfect trip!

Whether you are looking to catch a wave, catch a fish, or catch an unforgettable sunrise, our Ocean City Beach guide is for you!


You can’t get the full Ocean City experience unless you take in the bay life. This guide will show you all the bay adventures waiting for you!


The famous Ocean City boardwalk is on everyone’s bucket list! This guide will tell you everything you need to know about where to shop, eat and more!

What Makes Us Different

We are a small, military family run vacation rental business with a passion to give every guests the best experience on their vacation! The locations of our vacation homes are all places our family has treasured all our lives and we love giving others the chance to make life long memories in these special places. We also have put our own blood, sweat and tears into each property and designed every, small detail with the efforts to provide the best vacation experience for each and every guest!


One thing that has been really important to us as a family is wanting to make the world a better place because of Mad Men Vacation Rentals. God specifically put it on our hearts to do something globally and locally to make this difference. For our global efforts we make a $10 donation to an orphanage in Haiti called “Kay Marie” for every single reservation at all our properties. Check out their amazing non profit here: www.Haiti180.com

For our local efforts, we donate a getaway trip annually at Mad Men Lake House to a local maternity home called Mary’s Home.  This home provides a safe home environment with holistic services for expectant mothers in crisis and their children. The staff at Mary’s Home will take their current mothers with their children on a free vacation retreat to have some much needed rest, relaxation and FUN in Deep Creek Lake.


We believe doing a little makes a big difference and when you book with us you are also part of making the world a little bit better.  It is only because of our guests any of this is possible. So THANK YOU! We truly hope we can be part of your family’s best memories while making the world a better place all at the same time! We hope to host you soon!

Why Book With Us?

Deal directly with the rental owner

Deal Direct With Owner

Best Price Guarantee

Best Price

Family Run Business

Family Run

No Booking Fees Ever

No Booking Fees

Shared Local Knowledge

Shared Local

Secure Payment

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If you have any questions regarding the areas, the properties or availability please drop us a line

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Or call/text Rebecca: 301-275-9078

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