Holiday rentals in The Sleeping Bear

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Top-rated holiday rentals in The Sleeping Bear

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Top guest favourite
A modern tiny house nestled in a forest, surrounded by tall trees and lush greenery. The dark exterior contrasts with natural woodland elements. A spacious deck is visible, equipped with seating, inviting relaxation amidst nature.
Tiny home in Lake Ann
4.99 out of 5 average rating, 308 reviews

The Underwood Tiny House - with private hotub

Fall into the rabbit hole to experience our unique twist on a Wonderland inspired tiny house. Boasting a Queen size bed, a full kitchen and bathroom, and everything in between, you are bound to have a relaxing getaway... with a little bit of adventure! The spacious deck (with hot tub) overlooks the forest, and it is the perfect place to enjoy a cup of coffee or a glass of wine. The Underwood Tiny House has been created to give each person who walks through its door an experience like none other!

Guest favourite
A cozy living area features a blue sofa adorned with patterned cushions, positioned beside a round coffee table. Soft light is provided by a lamp and a small side table, enhancing the rustic charm of the log walls and inviting atmosphere.
Cabin in Maple City
4.89 out of 5 average rating, 289 reviews

Grandpa's Little Cabin-Across Big Glen

Stay at our classic, tiny log cabin from the 1940s. Originally the front office for the log cabin retreats on Glen Lake, more recently this was 'Grandpa's Little Cabin', providing decades of family memories. Located across from Old Settler's Park, it is situated in a beautiful, woodsy surrounding, with the benefits of the park's dock access and sunset views. Located just a short drive from Glen Arbor, The Dunes and all that Leelanau offers. Come see Up North as it was originally intended.

Guest favourite
The cottage features a bright yellow exterior surrounded by lush greenery. A small wooden deck holds a table with two chairs, inviting relaxation in nature. A charcoal grill is positioned nearby, with a window revealing the cozy interior. Fall leaves blanket the ground.
Cottage in Honor
4.89 out of 5 average rating, 272 reviews

Lemon Drop Cottage

This place is a winter and summer wonderland. Our cottage is a small 50's style with much character tucked away in the woods. We’re surrounded by the 70,000 acre Sleeping Bear Dunes. There’s plenty of skiing, canoeing, hiking and fishing, peace and quiet. We're on the boarder of Benzie and Leelanau Counties, the best of wine regions this side of the Mississippi and a true artisanal food destination It's a short drive to Honor, Empire or Glen Arbor. Traverse City is 25 miles east.

Top guest favourite
A charming log cabin is surrounded by vibrant autumn foliage, with colorful leaves scattered across the manicured lawn. A stone pathway leads towards the entrance, framed by a beautiful garden featuring blooming flowers amidst the rustic wood exterior.
Cabin in East Jordan
5 out of 5 average rating, 234 reviews

Cheerful Six Mile Lake Log Cabin.

Enjoy the coziness of a bygone era while staying in this 1940s quaint, storybook log cabin. The Hawks Nest has been lovingly restored to its original glory while having all the modern-day amenities woven through its clean 380 sq. ft. space. Retreat to the spacious covered porch to relax and view the acre-and-half property leading down to 100ft of 6Mile Lake frontage. Star gaze while relaxing in the comfortable, Amish-built gilding chairs around the spacious, paver fire pit area .

Top guest favourite
The exterior of the home features a two-story design with large windows and a wrap-around balcony. The structure is elevated on stilts, showcasing a blend of modern materials, including wood and stone accents. Outdoor seating and a grill are positioned on the patio area.
Tower in Empire
4.93 out of 5 average rating, 115 reviews

Exodus: Luxury Tower- Hot tub Near Sleeping Bear

Welcome to the Exodus Watch Tower, our newest addition offering stunning views and a luxurious space perfect for a getaway in the heart of Empire This home presents a unique and unforgettable experience from the panoramic window view and convenient wet bar, to the wrap-around balcony and relaxing hot tub Despite being the perfect hideaway, you are only: 5 min from Empire Beach 5 min from Sleeping Bear 10 min from Glen Arbor 20 min from Traverse City 30 min from Crystal Mountain

Top guest favourite
A charming A-frame house is reflected in the calm lake waters, surrounded by lush greenery. A small outbuilding is visible nearby, with a backdrop of trees creating a serene environment. The clear blue sky enhances the tranquil setting.
Home in Lake Ann
4.99 out of 5 average rating, 98 reviews

Sweet Lake Retreat | Adult Only | 20 mins from TC

Adult only•Romantic Getaway•Mindfulness Retreat•Sweet Lake Retreat is a one of a kind experience in Northern Michigan. *Please note we have a house being built behind us all of 2025, so there will be some construction noise during the work day.* Located in Lake Ann, just 20 minutes from downtown Traverse City and 20 minutes from Sleeping Bear Dunes National Lakeshore. We can’t wait for you to enjoy our hidden gem, a charming A-Frame nestled amidst the beauty of nature!

Top guest favourite
The exterior of a round, recently renovated home is surrounded by lush greenery and colorful flowers. Large windows offer views into the living space, while an inviting patio features seating and a grill. The unique architecture blends harmoniously with the natural landscape.
Dome in Glen Arbor
5 out of 5 average rating, 268 reviews

The Round Haven with Big Glen Lake Access

Experience living in the round. This recently renovated home is a super energy efficient 30 ft diameter circle. We are situated in the heart of Sleeping Bear National Lakeshore and a 300 ft walk to a secluded public access on Big Glen Lake. A place to adventure, relax and restore: this home is designed for sustainability and comfort. The perfect home base to explore the wonder of Sleeping Bear and surrounding quaint towns. We hope you find inspiration and rejuvenation.

Guest favourite
The geodesic dome is situated amidst a forest at night, with warm light emanating from its large windows. The unique architectural design is highlighted by the contrasting dark surroundings of tall trees, creating a striking visual against the night sky.
Dome in Benzonia
5 out of 5 average rating, 7 reviews

Löyly Luxury Dome | Michigan | Private Amenities

Löyly at Glamp Michigan is a luxury, private geodesic dome in a pristine Michigan forest... -Private hot tub, fire pit, and Blackstone. -Reservable sauna and cold plunge for privacy. -Sleeps four with one king and queen in loft. -Full kitchen, bathroom, living area. Incredible location in Michigan! -Crystal Mountain (5 mi) -Lake Michigan at Arcadia (12 mi) -Crystal Lake (8 mi) -Sleeping Bear Dunes (30 mi) -World-class golf (12 mi) -Fishing in the Betsie River (2 mi)

Top guest favourite
The cabin is nestled among tall grasses and wildflowers, with a large tree providing shade. Its dark exterior contrasts with the vibrant colors of the surrounding nature. The roof is metallic, and multiple windows reflect the greenery of the wooded area in the background.
Cottage in Northport
5 out of 5 average rating, 329 reviews

The Granary Northport . Rustic Modern Seclusion

Voted one of the top 85 Airbnbs by Conde Nast Traveler. The Granary is a lovingly restored two bed + one bath cabin located on 12 wooded acres with a secluded Lake Michigan beach nearby. A short drive to town will give you access to restaurants, groceries, breweries and wineries. Dogs are welcome! Please message us to discuss bringing more than 1. Absolutely no cats or other pets are allowed. We do not have a TV, but we do have fiber optic high speed internet.

Guest favourite
A spacious dining area features a large table surrounded by comfortable chairs, with sunlight streaming through floor-to-ceiling windows that offer views of the surrounding forest. A cozy seating area with a dark sofa and a decorative rug complements the natural light and warmth of the space.
Home in Cedar
4.95 out of 5 average rating, 242 reviews

Lincoln Lodge: Secluded~Wineries~Dog Friendly

🌲 Secluded 4-Acre Hardwood Retreat 🐶 Pet-Friendly for Family & Friends 🏞️ Covered Porch with Wildlife Views 🌅 Floor-to-Ceiling Nature Windows 💻 Fast 300 Mbps Wi-Fi Hosted by Catered Stays Rentals, we cater to the ideal guest experience, ensuring your comfort and satisfaction. Enjoy a secluded 4-acre property immersed in nature, perfect for both relaxation and adventure. Explore nearby attractions, unwind, and create lasting memories.

Top guest favourite
Cabin in Traverse City
5 out of 5 average rating, 43 reviews

Luxury Couples Retreat W/Hot Tub in Traverse City!

Escape to Rise Retreat, a newly renovated luxury tiny cabin on 6 private acres just 18-minutes from downtown Traverse City. Unwind in the hot tub under the stars, explore nearby trails, or cozy up by the fire. Designed for couples or small groups, this peaceful hideaway blends rustic charm with modern comfort. Featuring a full kitchen, two queen beds, and thoughtful details throughout. Your perfect Up North getaway starts here.

Guest favourite
A dock extends into the calm lake, with several chairs leaning against the railing. The sun sets on the horizon, casting soft hues of orange and blue across the sky. Gentle ripples in the water reflect the fading light.
Cottage in Empire
5 out of 5 average rating, 13 reviews

The Drake

Happy, Great light, Very comfy, Blue, yellow and white interior a place to feel at home in.Play yard for kids, Two fire pits one on the lake.With all the fire wood you would need. Great family vacation or just a wonderful little romantic get away Over Looks Sleeping Bear Dunes, My place includes 1 sofa bed. one full bed. I leave condiments here so you don’t have to bring them. Bring chair cold if you want to grill.

Popular amenities for The Sleeping Bear holiday rentals

Frequently Asked Questions

  • Where is The Sleeping Bear located?

    The Sleeping Bear is found along Michigan’s northwest shoreline, nestled in a scenic area shaped by dunes, forests, and lakes. It is known for expansive natural beauty and is surrounded by small villages and local communities.

  • When is the best time to visit The Sleeping Bear?

    Many people explore The Sleeping Bear between late spring and early fall, when temperatures typically range from 42–76°F (6–25°C) and outdoor activities are popular. Expect cooler, snowier conditions during the winter, with highs usually below 29°F (-1°C).

  • What are some things to do near The Sleeping Bear?

    You can explore hiking trails, scenic overlooks, and sandy beaches, while nearby villages often have locally rooted shops, galleries, and eateries. The region has opportunities for kayaking, wildlife spotting, and interpretive nature programs suited to various interests.

  • How is the weather near The Sleeping Bear?

    Expect cold and snowy winters, with lows near 12°F (-11°C). Summers are comfortable, often reaching 75–76°F (24–25°C), and rainfall stays moderate most months, so it’s common to experience mild days amid lush scenery.