Holiday rentals in Pleasant View

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.

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.

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.

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!

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.

Woods Cabin- Golf + Ski

Welcome to the estate! Spend time in nature by unwinding on acres of breathtaking, wooded property. This custom-built cabin is the guest house to a stunning 7,000sqft home that shares 20 acres, but tucked down a private path far in the woods from the main house. Our guest cabin is perfect for a small group or those just looking to escape! During your stay, enjoy full access to the property for grilling, snowshoeing, bonfires, petting the horses and more. Ski resorts & golf within 5 minutes!

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.

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.

10 Acres, firepits, Harbor, Petoskey, sleeps 14

Welcome to your private 10-acre Up-North getaway near Harbor Springs, Boyne Highlands, and Petoskey, perfect for summer vacations, golf trips, and large group getaways. With space to sleep up to 14 guests, this home is built for long lake days, outdoor nights, and time together. Whether you’re golfing, grilling on the decks, spending the day on the lake, or unwinding by the fire under the stars, this home is designed for unforgettable Northern Michigan summer memories.

Game & Exercise Room | Dog Friendly! (Sleeps 14)

🌲 Private Up North Retreat on 11 Acres | Game Room + Trails + Close to Ski & Golf Escape to Northern Michigan and experience the perfect blend of privacy, space, and year-round adventure just 5 miles north of Harbor Springs. Set on 11 secluded acres, this beautifully appointed home offers everything you need for a relaxing getaway or an activity-filled stay — from on-site ORV/ATV trail access to being just minutes from skiing, golf, and beaches.

Disconnect at our Ski Chalet in Nubs Nob

Newly remodeled A Frame Cabin in the woods of Hidden Hamlet in Harbor Springs, Michigan. Located in the little neighborhood at the base of Nubs Nob Ski Resort, this is a peaceful and quiet neighborhood surrounded by beautiful trees. Currently we are renting this as an open bedroom loft with a queen bed. There is also a pull out sofa sleeper on the main floor, but you know the comfort level of those... Check us out on Instagram @potters_cottage

Upper Deck: Boyne Carriage House

Welcome to the Upper Deck! This above garage unit has been extensively updated and is located directly across from Boyne Highlands Golf Center access. Featuring one queen bedroom, a spacious bathroom and open concept living / kitchen area, the space is compact and efficient, but perfect for 1-2 people (4 including the queen futon, but that’s going to be cozy!)