Holiday rentals in Pleasant View

4.92 out of 5 average rating, 134 reviews

The Nature Retreat - NEW hot tub & piano

A unique experience for people who appreciate the simple things of life - like nature, a good book and music. Located in a peaceful neighborhood near the Tunnel of Trees, Pond Hill Farm, downtown Harbor Springs, 8 minutes to Boyne Highlands and other top northern Michigan attractions. LUXARY HOT TUB INSTALLED JULY 2025. Upright piano and ukulele. House = approx. 2,800 sq. ft. You must let us know if you would like to bring 1 dog or an 8th person. Guests must be comfortable with stairs.

The exterior of a wooden house is nestled among tall trees, featuring a warm brown finish. A welcoming front door is flanked by a large window, and a decorative star adorns the side of the house. A gravel pathway leads to the entrance, surrounded by lush greenery.

4.98 out of 5 average rating, 161 reviews

Highland View Cottage of Harbor Springs

Our home is beautifully decorated, spacious, and very clean. It is your home away from home. Relax and enjoy the many amenities it has to offer. Whether you like to cook or eat out, our home has all the comforts of home. It is a SMOKE FREE and PET FREE home. Our guest MAXIMUM IS 8. Highland View is a great place to gather with friends and loved ones to create memories for years to come. Other things to do: Mackinac Island 35 minutes away Fishing Golf Skiing Biking Hiking Beaches Etc.

The exterior of the vacation rental home is showcased, featuring a blue facade with large glass windows. A pathway made of stones leads toward the entrance, framed by a mix of bare trees and patches of snow on the ground.

4.86 out of 5 average rating, 21 reviews

Orange Door Haus

Pack your bags and head to this 3-bed/3-bath vacation rental home in the charming town of Harbor Springs! The home’s unbeatable location offers easy access to skiing, local wineries, and endless opportunities for all-season outdoor adventure. Spend days perusing the shoreline of Lake Michigan, exploring local hiking trails, or hitting the slopes at Boyne Highlands or Nubs Nob Ski Resort. Bring days to a close by watching a movie on the Smart TV or sharing a drink with friends by the fire pit.

The exterior of the home features a light-colored facade with green shutters, surrounded by lush greenery and trees. A welcoming staircase leads to a front entrance, which is adorned with an American flag. The front yard is spacious, with well-maintained grass and landscaping.

4.94 out of 5 average rating, 104 reviews

Cozy retreat near local resorts, skiing/golf

Located just two minutes away from The Highlands and Nubs Nob ski/golf resorts, and only ten minutes away from the beautiful downtown shopping districts of both Harbor Springs and Petoskey, this charming Northern Michigan getaway is fully stocked for your vacation! This home away from home is fully outfitted to make your stay as comfortable as possible. We have also taken great care to ensure that it is one of the cleanest and tidiest homes available to you. Thank you for your consideration!

Apartment in Harbor Springs

A spacious multi-level condo is nestled among the trees, featuring large windows that provide ample natural light. A wooden deck extends from the main structure, furnished with chairs for outdoor relaxation. The design reflects a modern aesthetic, blending harmoniously with the surrounding nature.

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!

4.88 out of 5 average rating, 130 reviews

Guest suite in Harbor Springs

A welcoming living area features a comfortable brown leather sofa paired with a cozy armchair. A wooden coffee table sits in front, and a flat-screen TV is mounted on the wall. Natural light enters through a window, enhancing the simplicity of the space.

Private 2BR Loft in Harbor Springs

Comfortable pet friendly upper loft (2nd floor) located minutes from downtown Harbor Springs (6.6 mi). Notable attractions include: • Nubs Nob (6.4 mi) • Tunnel of Trees (6.7 mi) • The Highlands (7 mi) • Snowmobile trails (0.5 mi) • Easy access to many area mountain bike trails • Petoskey State Park (11.3 mi) • Pellston Airport (14 mi) • Inland Waterway Burt Lake (14.8 mi) • Mackinac Bridge (30 mi) Owner is on site in the main house, but you will enjoy your own private entrance and space.

4.99 out of 5 average rating, 202 reviews

Cottage in Harbor Springs

A comfortable living room is featured, with a large sectional couch and two armchairs arranged around a rustic coffee table. A gas fireplace is centered on the white-brick wall, complemented by a wall clock and framed artwork. A Smart TV is mounted for easy viewing.

Up North Lodge that checks all boxes! W/ AC

Experience everything Northern Michigan has to offer! Our 4 BR, 2 full bath Lodge is the perfect getaway that meets all of your needs. Relax by the fire, gather in the fully equipped kitchen & entertain in the large finished basement w/ a 75" Smart TV & pool table. This four seasons offering is centrally located to Nubs Nob/The Highlands (3 minutes), Harbor Springs (8 minutes), Petoskey (10 minutes) and renowned golf courses/restaurants. Come make memories that will last a lifetime!

4.96 out of 5 average rating, 123 reviews

Superhost

The Grand Cedar Lodge- Hot Tub + Golf + Ski

Highlandview Farms is the perfect, all-season retreat. Sitting on 20 breathtaking acres, this 7,000 sqft custom-built, cedar home with room for guests looking to enjoy time together, while having their own separate spaces. Enjoy full access to the property for games, the hot tub, grilling, snowshoeing, bonfires and more. Close to many golf courses, Nubs Nob & Highlands for winter sports too! This is a separate, limited listing from experienced hosts since 2017- see other listings reviews.

An open living area features high wooden beams and a cozy seating arrangement. A distinctive swing chair is shown, adding a playful touch. Natural light floods in from windows, complemented by warm wood tones across the walls and flooring, creating a welcoming space.

4.95 out of 5 average rating, 20 reviews

Harbor Springs Hot Tub Chalet! Ski/Golf/Play Boyne

Welcome to our (pet friendly) Up North cabin, ideally located across from Boyne Highlands property. World-class skiing and golf just 2 minutes away, and the beauty of northern Michigan at your finger tips. Lakes, beaches, incredible shopping/dining in Harbor Springs and Petoskey are all within 15 minutes. This home features 3 bedrooms / 2 bathrooms, a hot tub and can easily fit two families (upstairs / downstairs) Open layout and plenty of outdoor space for all to enjoy. Come stay awhile!

5.0 out of 5 average rating, 397 reviews

A cabin is nestled among lush green trees, featuring a sloped roof and a combination of wood and green siding. Large windows allow natural light to illuminate the interior. Surrounding foliage creates a serene and private atmosphere.

Cabin in Harbor Springs

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.

The kitchen features rich red cabinetry and a spacious granite island with wooden stools. Large windows provide natural light and a view of the surrounding trees. Modern appliances are integrated into the design, complemented by exposed beams in the ceiling.

4.96 out of 5 average rating, 92 reviews

4k sqft Log Chalet, Chef’s Kitchen, no fees, pets!

Your dream northern escape awaits. Custom 3 level Scandinavian artisan custom designed hand- hewn log lodge with room for 12 has 4 bedrooms, 2.5 bathrooms, hot tub, and 2 stone fireplaces. This lodge has newly updated luxury amenities. Your dream lodge is located only a few minutes from The Highland’s resort with world class golf, tennis, mountain biking, as well as zip lining. 10 minutes from beautiful Petoskey and Harbor Springs with great shopping and dining options.