Family-friendly holiday rentals in Rochester Hills

The Woven Oak - Cozy Getaway w/ Game Room & Bar

Welcome to The Woven Oak — a cozy North Royal Oak bungalow designed for connection, comfort, and style. Whether you’re here for work or play, this home offers the perfect blend of mid century charm and modern convenience Minutes from Downtown Royal Oak & Clawson, and just 18 minutes to Midtown Detroit, The Woven Oak offers easy access to top restaurants, cafés, and nightlife while sitting on a quiet, tree-lined street that feels worlds away from the city rush. You’re going to love staying here

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.

Detroit Canal Retreat

Secluded hideaway in the “Venice of Detroit”! Perched right on the historic Detroit canal system, this urban tiny house is a cozy retreat for couples or solo adventurers. Whether you’re here to kayak, cast a line, or just kick back with a book and a breeze, you’ll find plenty to love. Located in one of Detroit’s most unique—and real—neighborhoods. This is a revitalization zone with character: some blight, sure, but also a strong sense of community, and a refreshingly diverse, welcoming vibe.

MOD Mid Century 1964 A-frame with game room

1964 Mid Century A-Frame - romantic getaway. Short walk to lake, large wooded lot, outdoor fire pit, dining, BBQ grill, hot tub & bikes. Large bathroom w/ jacuzzi tub, open floor plan w/ large kitchen & living area w/ electric fireplace. Two upstairs bedrooms. Master has queen sized bed, work space & balcony. Front bedroom w/2 futons & overlooks the living room. Basement game room w/ sauna, pool table, foosball, shuffleboard, Jenga & laundry. Close to shopping, golf, ski resort, cider mill.

Designer Gem | Hot Tub | Quiet Neighborhood

Step into the spacious 2BR 1Bath designer home nestled just a stone's throw away from the Beaumont Hospital, vibrant downtown area, and many more attractions and landmarks. Explore Berkley and Detroit or lounge the day out in the backyard with the high-end hot tub. The stylish design and rich amenity list will leave you in awe. ✔ 2 Comfortable BRs ✔ Open Design Living ✔ Full Kitchen ✔ Backyard (Hot Tub, Dining, Lawn) ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Workspace ✔ Free Parking See more below

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.

Spacious Farmhouse with Breakfast - Ella's Place

Right by Rochester Hills downtown! Off of 75 and M59! 12 minutes from DTE center! 7 minutes from Great Lakes Crossing! 30 minutes from downtown Detroit! Walking distance from OU! Come relax in my Auburn Hills home! A modern interior with an elegant space will make your time here wonderful! Whether it's a family vacation, romantic getaway, or business travel, this home has everything you need. Wind down with a jetted bathtub. Create an exquisite meal. Host an event. Enjoy yourself!

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

Cabin 1: Horses & Hot Tubs on Perry Lake

This is one of 4 guest cabins on the property. We are an adults-only venue except for special Family Weeks. Please inquire about our kid-friendly dates. You'll be visiting the High Line cabin at Stillwater Stays. This upcycled shipping container is cantilevered above an old-growth forest and perched 70’ above Perry Lake. Finished in 2022, the premium interior feels fresh and modern. Guests enjoy lake access, encounters with horses, bird watching, and acres of hiking trails.

Best View on the Lake

4 Season Rustic Cabin with luxurious feel and first class views. *Lake Orion has a modern downtown while still trying to hold on the the small town charm. Clarkston & Rochester offer a change of scenery or different night life. Both within 15 minutes. *Offers awesome back way into Pine Knob music Theatre. 15-20 minutes. *2026 improvements: New Natural Gas Stove in living room New living room flooring *Sorry No Pets...Too many issues in the past.

Aesthetic ranch style home with modern furnishings

Immerse yourself in luxury at our recently renovated designer retreat, seamlessly blending beauty and convenience. Nestled near Rochester, Royal Oak, and Birmingham, this home exudes an inviting charm. Each bedroom features a high-end king-size mattress, and heated floors throughout, promising unparalleled comfort. Our meticulous housekeeping and attentive host guarantee a delightful stay. Book now and experience the pinnacle of refined living.

Gorgeous Comfy Downtown Clawson Home

Our newest stylish and comfy home steps away from Clawson downtown. This home is perfect for family & friends in this beautiful suburb of Detroit. It features a fully automated espresso machine with locally roasted Sabbath coffee beans, a large wooden deck with privacy walls, Samsung Frame TV featuring Netflix and Disney+, 3 stylish bedrooms with top-of-the-line hotel linens from Standard Textiles and plenty more.