Transformative Travel LLC

Transform your world with meaningful travel in Maryland.

Over 1,400 expereinces in Maryland for a range of budgets and private homes.

Discover Maryland’s natural beauty and vibrant community with H.E.A.R.T. Our selection of over 1,400 private vacation homes offers something for everyone – from history buffs to adventure seekers. 

Whether you’re hiking, kayaking, or birdwatching, we have the perfect local experience to suit your budget and preferences. Gather your family or friends for a reunion or retreat, or plan a group trip that everyone will love. 

With our curated selection of experiences, you can relax, recharge, and reconnect with what really matters. Come follow your call to adventure in Maryland!

Fly Fishing

Enjoy fly fishing lessons in Maryland's Patapsco River. Catch trout, small mouth bass, sun fish and learn the basics of a fly cast.

Calvert Cliffs

Explore Maryland ancient past with your seasoned guided & private access. All fossils found are yours to keep (tour duration: 4 hours)

Local Events

Come enjoy local events, shopping, culinary expereinces, adventures and historic sights in Ellicott City, Maryland.

Kayak Fly Fishing

Enjoy fly fishing lessons in Maryland's Patapsco River. Catch trout, small mouth bass, sun fish and learn the basics of a fly cast.

Sunset Paddle

Join Transformative Travel founders, Misty Dhillon and Aikta Suri for an exclusive Transformative Travel Sunset Paddle.

Maryland Heights

Enjoy a beautiful day of bonding, pampering, and sipping in the gorgeous natural and historic sites of the Harper’s Ferry area.

Explore Maryland's iconic expereinces from YOUR OWN HOME.

Over 1400 Vacation Homes in MD.

$199 per night

Charming getaway, sleeps 4 guests, features 1 bedroom and 1 bathroom, located in Cumberland, Maryland.

$195 per night

Beachfront escape sleeps 4 guests, features 1 bedroom and 1 bathroom, located in Ocean City, Maryland.

$195 per night

Enjoy access to the Potomac river for 6 guests, features 2 bedrooms, 1 bathroom in Brunswick, Maryland.

$199 per night

Enjoy waterfront views for 8 guests, features 2 bedrooms and 2 bathrooms, located in Ocean City, Maryland.

$175 per night

Beach getaway for 6 guests, features 2 bedrooms and 2 bathrooms, located in Ocean City, Maryland.

$165 per night

Enjoy ocean views with room for 4 guests, featuring 1 bedroom, 1 bathrooms in Ocean City, Maryland.

$199 per night

Farmhouse retreat sleeps 2 guests, features 1 bathroom, located in a farm close to Emmitsburg, Maryland.

$130 per night

Beach getaway sleeps 4 guests, features 1 bedrooms and 1 bathroom, located in Ocean City, Maryland.

$210 per night

Newly built in northern Ocean City, this home sleeps 8 guests, features 3 bedrooms, 2 bathrooms.

$175 per night

This Baltimore townhome sleeps 2 guests, features 2 bedrooms, 2 bathrooms and a fully set kitchen.

$150 per night

Enjoy beach access, sleeps 5 guests, features 1 bedrooms and 1 bathrooms, located in Ocean City, Maryland.

$145 per night

Waterfront property sleeps 8 guests, features 2 bedrooms, 2 bathrooms, near Ocean City, Maryland.

$135 per night

Lake front home sleeps 4 guests, features 1 bedroom and 1 bathroom, located in Oakland, Maryland.

$95 per night

Enjoy ocean views for up to 6 guests, features 1 bedroom and 1+ bathrooms, located in Ocean City, Maryland.

$210 per night

Ideally set home that sleeps 4 guests, features 2 bedrooms, 2 bathrooms, near Annapolis, Maryland.

$1,150 per night

Charming home for 8 guests, features 4 bedrooms and 2 bathrooms (1 half), located in downtown Annapolis , Maryland.

$1,250 per night

Large vacation home sleeps 26 guests, features 8 bedrooms and 7 bathrooms, located in Oakland, Maryland.

$1,345 per night

Located in Fishing Creek, Maryland, this historic victorian rental sleeps up to 18 guests, features 7 bedrooms, 2+ bathrooms.

$1,420 per night

Ocean front penthouse sleeps 8 guests, features 3 bedrooms and 3+ bathrooms, located in Ocean City, Maryland.

$1,350 per night

Signature oasis with lake front views sleeps 17 guests, features 6 bedrooms and 5 bathrooms, located in Swanton, Maryland.

$1,325 per night

Featuring expansive outdoor spaces this estate property sleeps 25 guests, features 9 bedrooms, 5 bathrooms, near Oakland, Maryland.

$2,250 per night

Create memories of a lifetime for up to 25 guests staying in this vacation home that features 8 bedrooms and 9 bathrooms, located in McHenry, Maryland.

$1,850 per night

Enjoy great value and host your next gathering or retreat for up 22 guests. Featuring 7 bedrooms and 5 bathrooms, this home is located in Oakland, Maryland.
GREAT VALUE

$1,185 per night

Enjoy waterfront access for up to 18 guests, features 6 bedrooms, 6 bathrooms, private pool, hot tub and pet friendly home located near Annapolis, Maryland.

$1,290 per night

This impressive home sleeps 14 guests, features 5 bedrooms and 5 bathrooms, located near Deep Creek Lake in Maryland.

$2,950 per night

Great retreat home that sleeps up to 34 guests, features 10 bedrooms and 11 bathrooms, located in Oakland, Maryland.

$1,850 per night

Lake front property (Chesapeake) sleeps 14 guests, features 7 bedrooms, 4 bathrooms, near Lake Ogelton, Maryland.

Ask an exert for more options!

We're here to help and support your travels.

Gift Cards

Make someone's day!

Travel can be a meaningful experience, and we believe everyone deserves to feel appreciated. That’s why we’re giving you the gift of meaningful experiences through travel.

Have a question? We're here to help, guide and mentor or facilitate meaningful travel and authentic connection.

Custom Tailor Your Package

Create your own experience!

If you’re looking for a different kind of experience, we’ve got you covered.

We specialize in crafting meaningful experiences, saving you both time and energy coordinating everyone’s interests by leaving the details to us. Just tell us what is calling you and then enjoy the ride!

Have a question? We're here to support your travels.

What makes us different from your average Travel Agent? 

We believe that every journey should be a conscious adventure, so you can consciously take forward the insights gained and transform your world through meaningful travel. 

We know that sometimes life gets in the way of your plans—that’s why we’re here to help. We’ll work with you to create a plan that works around your  schedule, travel companions but also your budget. Foster deeper connection through the lens of H.E.A.R.T and resilience. So that even if things don’t go according to plan, you can still enjoy the experience of traveling with us.

Do you already have a special journey planned but want to make it transformative? Perhaps a family vacation, a couple’s escape, a fishing adventure with a friend, or just some time away from home? If so, we would love to help!