Holiday rentals in Oakland Charter Township

Cranberry Lake Hideaway | Cozy Cottage w/ Sauna

Just minutes from DT Rochester, Lake Orion & Romeo, enjoy that “up north” feel without leaving Metro Detroit. We poured love into making this cottage cozy & unique—between the comfy beds, eclectic decor, & beautiful lake views, we hope it feels like a true retreat. Walk 5 mins to the lake, where you can kayak, fish, swim, or relax on the beach while the kids enjoy the playset. When you're ready to unwind, rinse off in the outdoor shower, relax in the sauna or end your night around the fire pit!

Updated & Comfy Private Home

Right by Rochester and AH downtown Off of 75 and M59! 15 min to Pine Knob! 10 min from Great Lakes Crossing! 30 min from Detroit. Walking distance from OU! Enjoy a stylish experience at this centrally-located place. This 2-bed, 1-bath home has everything you’ll need for a business visit or weekend away. Each bed room features a luxury queen bed. The kitchen is fully equipped with new quartz, stove, and coffee/tea bar. Check out the back with a deck, seating and fire pit, perfect for some R&R.

Best View on the Lake

Welcome to World Traveler owned home. *Amazing rustic experience in thriving Town on Lake Orion… *This upscale cottage is the perfect weekend getaway for all occasions. *The sunrises and sunsets alone make any vacation complete *Lake Orion has a variety of cuisine and bars. *Oxford, Clarkston & Rochester are all quite close. *Trolley that runs between Orion and Oxford *NEW 2025…NO PETS. Sorry but we had too many problems last year. *Also, strict check in and check out time… had issues!

Timberline / Indoor Pool / Arcade

Escape to our Shelby Township retreat, where luxury meets comfort in a 4-bedroom ranch-style home. Dive into the private indoor pool or challenge friends in the game room. The space boasts a gourmet kitchen for culinary exploits, an outdoor lounge for serene evenings, and plush bedrooms for tranquil rest. Ideal for families or groups seeking leisure and entertainment, this home is nestled in a quiet neighborhood, minutes from golf and shopping, ensuring a stay filled with cherished memories.

Downtown Rochester Gem!

Charming 2 bed/ 2 bath within walking distance to downtown Rochester, Michigan. Downtown Rochester has several great restaurants, shops, and walking areas for you and your family to enjoy. Apartment has a private entrance and use of a small outdoor patio area. Parking available in the rear of the building or street parking directly in front of the unit. Very unique property and location for your stay in Rochester area. Pets welcome but subject to an additional $25 cleaning fee

Cozy Stay Modern Comfort in the City

Step into the stylish and comfy 2BR-3BD-2BA oasis in the tranquil and friendly area of Rochester Hills. It promises a relaxing retreat just a few mins from the vibrant downtown, restaurants, shops, exciting attractions, and landmarks. The modern design, sunny pool area, and rich amenity list will satisfy your every need. ✔ 2 Comfortable Bedrooms (Sleeps 6) ✔ Open Design Living ✔ Full Kitchen ✔ Workspace ✔ Smart TV ✔ Wi-Fi ✔ Washer/Dryer ✔ Community Amenities (Pool, Gym, Parking)

Oakland Hills Farmhouse

Welcome to our updated peaceful retreat 3 miles from downtown Lake Orion and close to Addison Oaks and Rochester. Parks, swimming, biking, hunting, sporting clays, golf, and hiking all close by! We are connected to a non-profit working garden by a lovely wooded path. We are next to Marshview park and across the street from Bald Mt. state park and just a few minutes away from paint Creek Trail! Great location for a nature loving retreat and/or time away from the hustle.

Private Lake House Suite

Very nice private suite in lake house on col de sac at private lake in our home. If you like peace and quiet in nature setting this is it. Property is on a hillside, so guests are required to use steps and slanted walkways. We live above the suite and would like to share this beautiful place with you. Parking: please park on the street right in front of our house. Don't turn around in the neighbor's driveway across the street.

Lykke House - 5min Walk to DTRO

Enjoy your visit to Royal Oak in our peaceful and centrally-located place; just a short 5 minute walk from downtown Royal Oak full of a variety of restaurants, bars, entertainment, coffee shops and more! Long stays as well as short stays are welcome! Our place is tucked into a quiet, safe, walkable neighborhood close to many parks, Royal Oak Music Theater, Beaumont Hospital, Detroit Zoo, Downtown Detroit and multiple freeways.