Historic Up North Cottage Surrounded by Conservation, Lake & Nature

Lake Ann, Michigan
$525 avg/night
Minimum Stay 7 Nights
Bed 4

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 8

Max Sleeps

Night 7 nights

Min Stay

Private Lakefront Cottage Retreat on Ann Lake / Lake Ann

Happy Outlook is a secluded, historic Northern Michigan lakefront cottage tucked away on three private wooded acres at the end of a ¾-mile private drive. Surrounded by towering pines and birch trees, this early-1900s cottage blends classic Up North charm with modern comforts and sits on its own very private point on beautiful 530-acre Ann Lake.

With only two other homes along more than a half-mile of shoreline &; surrounded by 100's of acres of conservation, the setting is quiet, peaceful, and uncrowded—ideal for guests seeking privacy, nature, and a true lake getaway.

*** Private Lakeshore & Outdoor Living
Guests enjoy:
• 200 feet of private lakeshore
• Main patio on lake
• Private deck on lake with table, chairs & lounge chairs
• Two docks with ladders
• Separate kayak dock
• Outdoor shower
• Swimming raft: swim laps to and from dock
• Bonfire area - wood supplied
• Lakeside Adirondack chairs to relax, read a book or enjoy the loons
• Canoe, rowboat & two kayaks included

The retired owners live on property and are available if needed, their lakeside cottage set apart on separate shoreline, ensuring guest privacy.

Patio with Stone Fireplace & Outdoor Dining
The main lakeside patio features:
• A beautiful historic stone fireplace
• Wood-fired grill with prep area
• Charcoal BBQ & Propane BBQ's options
• Outdoor dining space - Umbrella & 8 chairs
• Patio wrapped in fragrant lavender, perennials and annuals

Whether grilling dinner, enjoying a campfire, or watching the sunrise, this is a favorite gathering spot.

Classic Cottage with Modern Comforts

This charming, casually comfortable cottage reflects its early-1900s roots while offering today’s conveniences—perfect for relaxed lake living rather than a polished resort feel.
• Unique Northern Michigan Location
• 1 mile to the village of Lake Ann
• General store & grocery
• Brew pub with evening entertainment
• Restaurants, library, parks, museum
• Tennis courts, pizza places, post office, churches
• 2 miles to Mistwood Golf Course (27-hole championship course)
•.12 miles to 12 other Golf Courses.
About 12 miles to:
• Interlochen Center for the Arts
• Lake Michigan
• Sleeping Bear Dunes National Lakeshore
• Traverse City
• Leelanau County

Close to everything—yet wonderfully private.
• A Place to Slow Down
• Happy Outlook is all about appreciating the simple things:
• Paddling quiet waters
• Fishing and swimming
• Hiking nearby trails
• Campfires under the stars
• Reading, local wine, and watching loons glide across the lake

Why Guests Love Happy Outlook...
✔ Private lakefront setting
✔ Quiet, uncrowded lake
✔ Classic Up North charm
✔ Excellent swimming & paddling
✔ Central location with total privacy

Other Things to Note
**Inquiries require a response within 24 hours so we can fairly manage availability.

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  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    1 Total Pets Pet Friendly Service Animals Exempt From Fees Welcoming Dogs Only
  • BEACH

    Beach Sun Loungers On The Beach
  • DINING

    Dining Table
  • SAFETY

    Deadbolt Lock Fire Extinguisher First Aid Kit No Carbon Monoxide Detector (host Has Indicated There Is No Carbon Monoxide Detector Or Gas Appliances On The Property) Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    4 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 1600 Sq Ft (149 Sq M)
  • KITCHEN

    Blender Cookware/dishes/utensils Dishwasher Electric Kettle Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Car Required Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Barbecue Grill Firepit Garden Outdoor Furniture Patio
  • BATHROOMS

    2 Bathrooms Bathtub Or Shower Hair Dryer Shampoo Soap Toilet Paper Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Birdwatching Nearby Boat On Site Casino Nearby Golfing On Site Kayak On Site Kayaking Nearby Marina Nearby Parasailing Nearby Power Boating Nearby Swimming Nearby Tennis On Site Water Sports Equipment Water Tubing Nearby Winery Tours Nearby
  • ENTERTAINMENT

    Books DVD Player Games Stereo Video Library TV
  • LIVING SPACES

    Dining Room Fireplace Wood Stove
  • FAMILY FRIENDLY

    Children's Books Children's Dinnerware Children's Games Highchair Playground
  • LOCATION HIGHLIGHTS

    In A Rural Location In A Village Near A Hospital Near Outlet Shopping Near The Bay On The Lake On The River On The Waterfront
  • SUITABILITY/ACCESSIBILITY

    No Elevators Note From Host: Outside Only, Pick Up Butts, Fire Safety! Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 8

Map Map

School District Availability

Review Review

  • jackie p.

    Submitted Aug 3, 2025

    Stayed Jul 27, 2025

    Wonderful location right on the lake. Loved seeing and hearing the loon family close by. Scott and Nancy couldn't have been more gracious and friendly. Would definitely consider staying here again!

  • Joe M.

    Submitted Jul 15, 2025

    Stayed Jun 29, 2025

    We had a wonderful time. The lake was peaceful and the accommodations were as described. Scott and Nancy were very welcoming and helpful.

  • kimberly m.

    Submitted Jul 30, 2024

    Stayed Jul 7, 2024

    Views and hospitality were magnificent!! Scott and Nancy are so very generous to share such a beautiful spot!

  • Julie M.

    Submitted Aug 16, 2023

    Stayed Jul 23, 2023

    Great house, great location and great hosts.

  • Paula M.

    Submitted Jul 16, 2023

    Stayed Jul 2, 2023

    Excellent property and near many attractions!

  • Sue C.

    Submitted Aug 5, 2022

    Stayed Jul 17, 2022

    Happy Outlook/Lake Ann Cottage was fantastic. We loved it! Being on the lake in such private setting made up for the few missing creature comforts like AC. (The bed was the most comfortable vacation rental bed...ever.) Location was ideal for exploring the area. We took advantage of the kayaks and canoe and managed to take the dog with us (without capsizing)! Our 7 YO Godson requested we come here every year. And if the dog could talk, he would second that motion. Can't wait to come back!

  • Dave M.

    Submitted Jul 15, 2022

    Stayed Jul 3, 2022

    A quiet and relaxing time surrounded by nature. Good fishing too.

  • Megan B.

    Submitted Jul 5, 2022

    Stayed Jun 26, 2022

    We simply loved our time at Happy Outlook! The cottage is secluded and rustic but still perfectly charming, clean and comfortable. Scott and Nancy were wonderful, friendly and helpful hosts. The views and lake are beautiful! We thoroughly enjoyed a quiet week of dock fishing, a bit of boating, loon watching and adventuring around the property and nearby beaches/attractions. Our small kids imaginations ran wild the entire time and we loved every minute! Thanks again Scott and Nancy! We hope to be back next year!

  • Jillian M.

    Submitted Sep 22, 2021

    Stayed Sep 12, 2021

    This is the perfect spot for rest and relaxation ! Lake Ann is peaceful and quiet ! Perfect sunrise viewing too! The natural areas surrounding the property , with wild life present made for a very special vacation with my family. I highly recommend this spot !

  • Ken S.

    Submitted Aug 19, 2021

    Stayed Aug 1, 2021

    Scott and Nancy provided an excellent retreat on Lake Ann. They provided excellent communication and wonderful suggestions to local events. Their property is remote and provided a serene setting to enjoy our end-of-summer retreat. We took advantage of all that the property offered (from the kayaks and canoe to the outdoor kitchen). It is really a hidden gem.

Your dates are Available!

Total

Includes taxes and fees
$625+
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