Holiday rentals in Oakland Charter Township

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Top-rated holiday rentals in Oakland Charter Township

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Guest favourite
A spacious living area features a gray sofa accented with decorative pillows, placed beside a coffee table atop a patterned area rug. Natural light filters through large windows, revealing views of the outdoor landscape. A stylish fireplace anchors the room, while wooden beams add architectural interest.
Cottage in Oakland Township
4.79 out of 5 average rating, 28 reviews

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!

Guest favourite
The living area features a cozy couch adorned with colorful cushions, paired with a glass coffee table. Natural light floods through large windows, enhancing the room's modern decor, including a stylish fireplace and an artwork piece depicting a map of Detroit.
Townhouse in Auburn Hills
5 out of 5 average rating, 6 reviews

*new* dt auburn hills lux condo

Step into comfort in this 2 BR 2.5 BA, stylish condo, with dining /kitchen table to easily accommodate a corporate group or medium sized family! ✔ 2 Comfortable Bedrooms + 2 Full BT & 1/2 BA ✔ 1 Pull out Sofa ✔ 30 mins to Detroit & 15 mins to Great Lakes Crossing Outlets ✔ Fully Equipped Kitchen ✔ TVs in LR & 1 Bedroom ✔ High Speed Wi-Fi ✔ FIreplace ✔ Cubby Office Space with monitors/desk ✔ 2-Car Attached Garage Learn more below! Enjoy a stylish experience at this centrally-located condo.

Top guest favourite
The exterior of the renovated lakefront property features a modern design with large windows allowing for ample natural light. A wooden deck is furnished with inviting chairs, and a grill is positioned nearby. A lush green yard offers a serene backdrop of trees.
Home in Oakland charter Township
5 out of 5 average rating, 23 reviews

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

An open living space is highlighted by a wooden ceiling and large windows, offering natural light. The area features a cozy seating arrangement with a gray sofa and a plush rug. A dining area is visible in the background, along with a staircase leading to the upper level.
Home in Oakland charter Township
4.71 out of 5 average rating, 38 reviews

Predmore Farm-in-the-Woods

Immerse the senses on 5 acre of private space tucked away in the woods. All four seasons bring serenity and nature to your doorstep. Glamping at its finest! Sleeps up to 12. Close to town but away from it all! Adventure on miles of hiking & biking trails out the front door Close to: Pine Knob Ski Resort/Music Theatre, Addison Oaks County Park, Upland Hills Farms, 30 minutes to Detroit, and several golf courses in the area. Within a few miles of Downtown Lake Orion and Rochester.

Top guest favourite
An open-concept living area features a modern kitchen with light wood cabinetry and stainless-steel appliances. A comfortable seating area includes a dark couch and an armchair. Natural light enters through large windows, illuminating the polished wooden floor and a central coffee table with decorative items.
Flat in Rochester
4.9 out of 5 average rating, 112 reviews

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

Superhost
A modern living room features a gray sofa with accent pillows facing a wall-mounted smart TV. Black armchairs are positioned nearby, and a sleek coffee table sits in the center. Soft lighting illuminates the area, creating a calm environment.
Flat in Rochester Hills
4.86 out of 5 average rating, 28 reviews

Urban Oasis Sleek, Cozy & Well-Located

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)

Top guest favourite
A large tree stands prominently in a green yard, featuring a tire swing attached to a sturdy branch. Lush greenery surrounds the tree, with a gentle slope leading to the base, creating a serene outdoor setting.
Home in Oakland charter Township
4.9 out of 5 average rating, 41 reviews

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.

Flat in Auburn Hills
4.78 out of 5 average rating, 45 reviews

Studio Apartment in Auburn Hills

Welcome to this cozy studio! This charming space has everything you need for a comfortable stay — a queen-size bed, a full bathroom with a stand-up shower, a kitchenette, and even a little workspace if you need to get things done. You’ll also find Wi-Fi, a TV (no cable), and fresh coffee to start your mornings right. We're just a few miles from delicious restaurants, Pine Knob Music Theatre, St. Joseph Mercy Hospital, and super close to I-75 and Great Lakes Crossing Mall

The living area showcases a cozy space with a plush sofa and a contrasting armchair. A large coffee table occupies the center, complemented by a Smart TV mounted on a wooden accent wall. The open kitchen is visible through an archway, adding to the room's inviting atmosphere.
Flat in Shelby Township
4.65 out of 5 average rating, 23 reviews

Lake Area 1BR Retreat | Pet-Friendly & WiFi

Unwind in this stylish 1-bedroom retreat in the heart of Shelby Township. Perfect for a weekend getaway, business trip, or extended stay, this cozy apartment features a fully equipped kitchen, Smart TV, and ultra-fast WiFi. Located just minutes from Van Dyke and Hall Road, you're close to top restaurants, bars, cafés, golf courses, and shopping. Explore scenic Stony Creek Metropark or take a quick 45-minute drive to downtown Detroit. Your peaceful escape starts here!!

Top guest favourite
A cozy bedroom features a spacious bed dressed in red and white linens, positioned beside a framed piece of floral artwork. A flat-screen television is mounted above a wooden fireplace, which is complemented by lanterns and decorative items on a nearby shelf.
Guest suite in Springfield Township
4.96 out of 5 average rating, 436 reviews

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.

Top guest favourite
A modern lake house is surrounded by lush greenery and trees, showcasing an expansive deck overlooking the water. A landscaped area features various plants and rocks, enhancing the natural setting. The structure blends harmoniously with the serene environment.
Guest suite in Village of Clarkston
4.97 out of 5 average rating, 748 reviews

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.

Home in Lake Orion
4.78 out of 5 average rating, 9 reviews

Hidden Gem

This little charm is situated on a scenic large lot on the canal that connects to Long Lake - All Sports Lake. Lake access from the canal or launch your boat from Bunny Run Beach. Lots of parks, trails and beaches to visit. The property provides tons of space for the family for different activities. Enjoy morning coffee on the large deck overlooking the water. Downtown Lake Orion is close by to explore too !

Popular amenities for Oakland Charter Township holiday rentals