Holiday rentals in Oakland Charter Township

Brushstrokes by the Lake Cottage

Charming and fully renovated cabin nestled by the serene lake. Offers an up-north feeling without the long drive! Important Note: construction until 11/21/25.Week days only - Neighbor finishing a garage siding. Futures: ~10 minutes away from Pine Knob concerts and ski resort. Only 15 minutes from Clarkston's delightful restaurants. Wake up to breathtaking lake views and natural beauty. Swim, kayak, or paddle board for some fun on the lake. Relax by the fire pit in the evening or enjoy a meal.

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!

Charming Studio in the Woods

Enjoy a peaceful stay in this charming studio in the woods. Get the best of both worlds - close to downtown Oxford for shopping and dining and located off the beaten path for a cozy country feel. It is located on a dirt road. This studio apartment is a private space located in our pole barn. It has been newly remodeled and includes a king size bed, queen size air mattress, and a sectional sofa. Perfect location for concerts at Pine Knob, weddings, and sporting events at Seymour Lake Twp Park.

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.

Cranberry Lake - Lakefront Home with Beach Access

From paddle boarding to ice fishing, enjoy all 4 seasons at Cranberry Lake. This Lakefront property will give you the experience of being “up north”, while taking a fraction of the time to get there. - Private Lake/Beach with boat launch (electric only) - 2 minutes from great fishing and hiking trails - 5 minutes from Addison Oaks and Cranberry Lake Park - 8 minutes from Big Red Apple Orchard - 10 minutes from Grey Stone Golf Course - 15 minutes from Downtown Romeo and Downtown Rochester

Modern A-Frame, Romatic Retreat, Pond, Nature

Welcome to The Shacks – The Evergreens Edition, a modern A-frame tucked in a grove of evergreens and overlooking a peaceful pond. This cozy, design-forward retreat is perfect for couples seeking nature, romance, and connection. Features a loft, extra bedroom and a full bathroom. Enjoy the walkout deck, complete with outdoor furniture, just off the deck you’ll find a fire pit for roasting marshmallows. A short path into the woods leads to a charming pond. *Pets must be added to reservation.

Paint Creek Trail Cottage • Cozy & Private

Charming Cottage on Paint Creek Trail Relax in our updated private cottage on 0.65 wooded acres with direct access to the Paint Creek Trail. Enjoy brand-new bedding and furnishings, cozy living spaces, and a peaceful backyard surrounded by nature. You’ll be minutes from Downtown Rochester, cider mills, Oakland University, dining, shopping, and parks. Walk, bike, run, or fish right from your backyard — perfect for couples, small families, or guests looking for a quiet remote-work retreat.

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

Trendy & Vibrant Unit City Experience

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.

Cozy Apartment in our Log Home.

Trim Pines is the perfect small space for a quiet stay and is enjoyed by guests in every season. Our lower one room walk-out is comfortable for 1 to 2 people for short or long term stays. It is a great place to unwind and relax. This tranquility is located 8 miles from I-75 in Davisburg, Michigan. Our guests enjoy local festivals and concerts at Pine Knob Music Theater, golf at nearby courses and biking and hiking at local County, Metro and State Parks.

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.