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Historic Up North Cottage Surrounded by Conservation, Lake & Nature

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Our Point surrounded by conservation. Old Sugarloaf ski area in the distance.
3/4 mile drive to our secluded point & preserved point beyond.
The point is shallow, we set markers & raft to warn boaters. Some don’t get it
Aerial view from across the lake
Calm blue day... unique spot for up north

Reviews

10 out of 10
Exceptional
4 bedrooms2 bathroomsSleeps 81600 sq ft

Popular amenities

  • On beach
  • Onsite parking available
  • Dog-friendly
  • Kitchen
  • Washer
  • Outdoor grill

Explore the area

View in a map
Lake Ann, MI
  • Place, Bryan Lake
    ‪3 min drive‬
  • Place, Lake View
    ‪3 min drive‬
  • Place, Lake Ann Brewing Company
    ‪5 min drive‬
  • Airport, Traverse City, MI (TVC-Cherry Capital)
    ‪32 min drive‬

Rooms & beds

4 bedrooms (sleeps 8)

Bunkroom

2 Twin Bunk Beds

Guest suite

1 Queen Bed

Lakeview Bedroom

2 Twin Beds

Master

1 Queen Bed

2 bathrooms

East deck & dock

Shower only

Guest Bathroom

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Master Bathroom

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer

Spaces

Deck or patio
Porch or lanai
Kitchen
Separate dining area
Outdoor play area
Garden

About this property

Historic Up North Cottage Surrounded by Conservation, Lake & Nature

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.
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Pet friendly
Free WiFi
Outdoor Space

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House Rules

Check in after 4:00 PM
Minimum age to rent: 35
Check out before 10:00 AM
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Children

Children allowed: ages 0-17
This is a family's nature paradise get away.
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Events

No events allowed
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Pets

Pets allowed: dogs (limit 1 total)
1 dog please. Please review with us.
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Smoking

Smoking is not permitted
Outside only, pick up butts, fire safety!

Check-out instructions

The host requires you complete the following before checking out:
Load and start the dishwasher
Strip any used beds and gather used towels
Remove personal items, remove leftover food and drinks, and take out the trash
Turn off the lights
Leave stripped beding on foot of the bed used.
Leave used towels in pile in tub / shower
Recycles taken to Twp recycling. Trash taken to dumpster at LA Grocery, go in an pay per bag. Bag size doesn't matter.
Failure to complete these may result in a negative review from the host.
One dog preferred. No dogs on beds or couch. Please have dog on leash. Tie up and a dog waste station with bags you dispose @ end of stay.
Please turn lights off when gone or or not using them. In case of rain you are responsible for closing windows down and porch shades.
*Inquiry Response Policy Inquiries require a response within 24 hours. If we do not receive a response, the dates may be released to other guests.

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there are no carbon monoxide detectors or gas appliances on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock

About the neighborhood

Lake Ann

Located in Lake Ann, this vacation home is in a rural area and on the beach. Front Street and Village at Grand Traverse Commons are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Sleeping Bear Dunes National Lakeshore and Lake Michigan. Traveling with kids? Consider Burnett Park, or check out an event or a game at Turtle Creek Stadium. Discover the area's water adventures with kayaking and snorkeling nearby, or enjoy the great outdoors with ecotours and hiking/biking trails.
View more Vacation Homes in Lake AnnOpens in a new window
Map
Lake Ann, MI

What's nearby

  • Bryan Lake - 3 min drive - 1.5 km
  • Lake View - 3 min drive - 1.8 km
  • Lake Ann Historical Society Museum - 4 min drive - 2.2 km
  • Lake Ann Brewing Company - 5 min drive - 2.9 km
  • Burnett Park - 5 min drive - 2.9 km

Getting around

  • Cherry Capital Airport (TVC) - 30 min drive

Restaurants

  • ‪Dilbert's Cafe - ‬15 min drive
  • ‪Light of Day Organics - ‬13 min drive
  • ‪Lake Ann Brewing Company - ‬5 min drive
  • ‪Wendy's - ‬17 min drive
  • ‪Bradley’s Pub & Grille - ‬18 min drive

Frequently asked questions

Is Historic Up North Cottage Surrounded by Conservation, Lake & Nature pet-friendly?

Yes, this property allows dogs (limit 1 total). Some restrictions may apply, so please contact the property for more details.

How much does it cost to stay at Historic Up North Cottage Surrounded by Conservation, Lake & Nature?

As of Apr 25, 2026, prices found for a 1-night stay for 2 adults at Historic Up North Cottage Surrounded by Conservation, Lake & Nature on Jun 21, 2026 start from $501, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Historic Up North Cottage Surrounded by Conservation, Lake & Nature?

Check-in begins at 4:00 PM.

What time is check-out at Historic Up North Cottage Surrounded by Conservation, Lake & Nature?

Check-out is at 10:00 AM.

Where is Historic Up North Cottage Surrounded by Conservation, Lake & Nature located?

Nestled on the beach, this Lake Ann vacation home is within a 15-minute walk of Shavenaugh Lake and Marys Lake. Sanford Lake and Tarnwood Lake are also within 2 mi (3 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 15 out of 15 reviews
Rating 8 - Good. 0 out of 15 reviews
Rating 6 - Okay. 0 out of 15 reviews
Rating 4 - Poor. 0 out of 15 reviews
Rating 2 - Terrible. 0 out of 15 reviews

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Paula M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent property

Excellent property and near many attractions!
Stayed 14 nights in Jul 2023
Verified

10/10 Excellent

kimberly m.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Vintage Cottage

Views and hospitality were magnificent!! Scott and Nancy are so very generous to share such a beautiful spot!
Stayed 7 nights in Jul 2024
Verified

10/10 Excellent

Julie M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Thanks for the memories!

Great house, great location and great hosts.
Stayed 7 nights in Jul 2023
Verified

10/10 Excellent

jackie p.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 7 nights in Jul 2025
Verified

10/10 Excellent

Joe M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful time. The lake was peaceful and the accommodations were as described. Scott and Nancy were very welcoming and helpful.
Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

Sue C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Absolutely wonderful!

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!
Stayed 7 nights in Jul 2022
Verified

10/10 Excellent

Dave M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice location on the lake

A quiet and relaxing time surrounded by nature. Good fishing too.
Stayed 7 nights in Jul 2022
Verified

10/10 Excellent

Megan B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Family Getaway!

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!
Stayed 7 nights in Jun 2022
Verified

10/10 Excellent

Jillian M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

The perfect spot

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 !
Stayed 7 nights in Sep 2021
Verified

10/10 Excellent

Ken S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic Getaway Retreat

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.
Stayed 7 nights in Aug 2021
Verified

10/10 Excellent

Maria G C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect in every way!

Cozy rustic charm on a beautiful lake. We were there with our two teen daughters and our dogs. The girls rated the vacation 11/10 and if the dogs could talk...20/10. Easy access to water for swimming, paddling or simply wading. Loons, eagles, frogs, fish, deer, song birds and two friendly garter snakes make regular appearances.. Great outdoor gathering spaces around a stone oven and charcoal grill or a fire pit. Wonderful onsite hosts. Town has a small market that literally has everything you need. Easy access to best ice cream in the country and Sleeping Bear/Arcadia Dunes. Dreaming of our next visit.
Stayed 7 nights in Jul 2021
Verified

10/10 Excellent

Jeffrey R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Such a special place!

This is a fantastic place- quiet and peaceful, perfectly situated for getting to Traverse City and Sleeping Dunes. The cabin is well equipped for everything you could possibly need; beds are comfortable; the lake views are fantastic. Scott and Nancy are there when you need them, with advice about things to do- but know not to be overbearing. We really appreciated that Scott made sure there was wood for the campfire and barbecue! We will stay here again if we can!
Stayed 14 nights in Jul 2021
Verified

10/10 Excellent

Kevin H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

A very relaxing, comfortable place to stay. Excellent hosts!

We had the most wonderful and relaxing time in the Lake Ann house. It's a great property with a great view and great amenities. The hosts are the best hosts we've ever had in a vacation rental experience. 10/10, would recommend!
Verified

10/10 Excellent

Stephanie W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fabulous Family Vacation Spot

This charming home right on Lake Ann is clearly well cared for and loved by the owners. VERY clean and adorably decorated. Lots of space for a family to enjoy. Anything you would need in the kitchen and at the water's edge. Perfect location between Traverse City and Lake Michigan.
Stayed 7 nights in Aug 2019
Verified

10/10 Excellent

Christine P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Girls week

Property peaceful, beautiful setting. Enjoy close proximity to nearby restaurants and activities. Should be noted that owner has home on property but is very personable. Love that he helped build loons nest and truly loved their songs and entertainment!
Stayed 7 nights in Jul 2019

About the host

Hosted by Scott Hedberg

Host profile image
Scott grew up on Lake Michigan in Glen Arbor and Nancy grew up on a dairy farm in Illinois. Scott & Nancy are University of Michigan and University of Illinois graduates respectively in Landscape Architecture. We have been married 45 years and we have 3 children and 7 grandchildren. We have owned the property for 38 years, purchasing it for our family's enjoyment.

Why they chose this property

A unique classic 100 yr. old cottage on a remote lakeshore on Lake Ann in Benzie Co. Near Leelanau Co. and Grand Traverse Co. Sleeping Bear National Lakeshore, Interlochen, and numerous wineries. It is central to many of the regions assets! The small town of Lake Ann is like stepping back in time with a General Store. The Lake Ann Brewing Co. has brews and evening entertainment for the family. The Stone Oven has great food to eat while enjoying the brew pub music. The property is at the end of 3/4 mile long private road and surrounded by hundreds of acres of conserved properties. The property itself has 300 ft of lakefront on 3 acres. It's our get-away to enjoy nature and "Up North". The woodpecker tapping, the loon calling and chatter of squirrels are our noisy neighbors. The lake has restricted high speed boating from 7:30 pm to 11 am. Most boaters respect that law.

What makes this property unique

The Lakefront features a main patio, deck area, docks, fire ring and outdoor shower. The main patio has an old stone fireplace with a wood fired grill & a charcoal grill, prep area and dining. The patio is wrapped with fragrant lavender in July & August. Canoe, rowboat and 2 kayaks are available for your use. Docks have ladders and we enjoy swimming laps to our raft and back, snorkeling or just floating. The point has a mud bottom so we swim off the east dock and use the outdoor shower after to avoid swimmer's itch. We haven't had a problem with the itch after installing the shower. Kitchen and baths are updated in keeping with the earlier times. The screen porch is great for meals and reading. We will be adding internet for 2021 by request however it's about getting away!

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