Family-friendly holiday rentals in Crooked Lake

Cozy retreat- Fall and Winter- Ski Nubs/Highlands

Cozy year round retreat-Relax on your deck or sandy beach just footsteps from your door on beautiful/private Round Lake. This comfortable studio condo offers lots of nearby summer, fall and winter events, 3.5 miles to Nubs and Boyne Highlands with colorful autumn and snowy events. Year round indoor pool & Hot Tub. Shop/Dine/Bike or Hike Trails & area attractions in Petoskey, Harbor Springs and Charlevoix. 5 min walk to the fabulous Toski Sands market for your food and beverages. Pickle B courts.

Indoor spaces · Family · Parking

The Hideaway of Crooked Lake

Looking for the perfect Northern Michigan escape? Be sure to check out this cozy cottage nestled on a private drive just steps away from Crooked Lake. Enjoy the uniqueness of an old, charming cottage along with some modern conveniences that will make your stay more comfortable. Located minutes away from Petoskey and Harbor Springs, heading out and exploring Northern Michigan could not be easier. Or stay at the cottage for kayaking, shared lake access, bike path, and local marina rentals.

Family · Kitchen · Sleep quality

Coveside Retreat: Beach, Pools, Hiking, Skiing

This large, end-unit 5-bedroom, 3 bath condo is great for large families or gatherings of friends at Harbor Cove. Tucked into the woods with nature trails to hike, sandy lake Michigan shoreline and indoor/outdoor pools. Close to golf courses and wineries. 5 miles from Boyne Highlands and Nubs Nob, for winter enthusiasts who enjoy skiing and snowboarding. A short drive, or bike ride to downtown Harbor Springs and Petoskey for dining, movies and shopping. Note this is not a party house!

Indoor spaces · Kitchen · Bathroom

Elkhorn Cabin:Ultra Cozy Experience: New King Bed

The Elkhorn Log Cabin, located in the scenic town of Wolverine, Michigan, has undergone a meticulous restoration to create an ambiance of warmth and charm. The restoration process involved the careful use of locally sourced, reclaimed woods and materials, resulting in a rustic yet refined atmosphere. The strategically placed windows provide stunning views of the surrounding forest and encourage natural airflow. In my opinion there is not many places that surpass this idyllic location.

Indoor spaces · Family · Barbecue

Lakefront A-Frame | Kayaks, Fire Pit & Hot Tub

Tucked among the pines on a quiet northern Michigan lake, Veaux Pines is a lakefront A-frame made for slow mornings, lake days, and cozy nights under the stars. Spend your days kayaking, paddleboarding, relaxing in the covered hot tub, or enjoying the newly updated outdoor spaces before gathering around the fire. Inside, warm wood details and thoughtful design make it easy to settle in after a day outside. Perfect for: • Couples getaways • Small groups • Peaceful Up North escapes

Kitchen · Indoor spaces · Parks

The Rhubarbary Ruins - with an outdoor sauna

We have just added an outdoor sauna to this fabulous cabin in the woods behind our house. Although there is only 1 proper bedroom there is a sleeping loft with a queen size bed and window overlooking the hardwood forest. We also have a pull-out couch. Guests have complete privacy and everything provided for a comfortable stay This is a cabin with peaceful relaxation in mind....no loud parties or anything of that nature. Come and enjoy northern Michigan's beauty in all seasons.

Kitchen · Family · Outdoor spaces

Charming Lakefront Guest Cottage

Charming, cozy guest cottage located on Crooked Lake just steps away from the water. Slow down, watch the sunrise, enjoy cool breezes off the lake and listen to the loons. Detached guest cottage with private entrance in a quiet location. Perfect for couples. Light & sunny interior w/beautiful lake views. Located between Petoskey & Harbor Springs with great dining & shopping. Enjoy a Northern Michigan summer, come for the amazing fall colors, or enjoy a cozy winter ski weekend!

Indoor spaces · Family · Heating

Tiny Home* 5 Min to Boyne Mtn. *Sky Bridge*BonFire

Escape to 13 peaceful acres just 5 minutes from Boyne Mountain. This 310 square foot tiny home sleeps up to 5 and offers a quiet farm setting while keeping you close to Boyne City, Petoskey, skiing, golf, beaches and trails. We're excited to share our land with more than a century of family history- and the serene Northern Michigan life we love- with you. Please note that due to the ladder-access loft and design of the tiny home, we welcome children ages 5 and older.

Kitchen · Family · Hiking

Welcome home to PENNY Cottage CVX! Renovated + A/C

Welcome to the updated Penny Cottage! Spacious in-town Charlevoix home. Thoughtfully designed interior with elevated materials and custom pieces throughout. The perfect spot to relax after a day of adventuring. 3 bed, 2 bath home with fully equipped kitchen & BBQ grill. A few blocks walk to Lake Michigan beaches or 1 minute car ride. Central A/C, Wi-Fi, Roku TV, books, games, puzzles and toys. Towels & linens provided. STR License: 270-175-00

Kitchen · Family · Biking

Sauna, Aframe Riverside Cabin on Sturgeon River

When you stay with us you'll step into the magic of Fernside, our beloved A-Frame retreat on the Sturgeon River in Indian River, Michigan. Imagine yourself waking up to warm sunlight and the soothing melody of the river. It's not just a getaway; it's your ticket to pure serenity and excitement. Fernside is where every moment feels like an adventure waiting to unfold. We can't wait for you to experience the joy of this cozy haven!

Family · Kitchen · Skiing

Little Bay Retreat: 2 Bedroom Downtown Petoskey!

Historic 2 bedroom home located downtown Petoskey, just two blocks from restaurants, shopping, and picture perfect million dollar views of Little Traverse Bay. Walk anywhere in town from this location! You'll love the three seasons sunroom - it's a great spot for morning coffee and evening card games. Grab dinner downtown and stroll the waterfront before heading home for the night at Little Bay Retreat.

Family · Kitchen · Bathroom

Modern Home of Style & Comfort | Private Hot Tub!

Welcome to your modern escape, where luxury meets nature in the heart of Petoskey’s stunning landscape. Tucked away for peace and privacy, yet just minutes from downtown, this contemporary retreat offers the perfect blend of serenity and convenience. Enjoy the best of both worlds—seclusion in nature with easy access to Petoskey’s vibrant charm.

Family · Indoor spaces · Sleep quality