10/10 Excellent
Paula M.
Jul 16, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent property
Paula M.
Stayed 14 nights in Jul 2023
Entire home
Historic Up North Cottage Surrounded by Conservation, Lake & Nature
Photo gallery for Historic Up North Cottage Surrounded by Conservation, Lake & Nature
Reviews
10 out of 10
Exceptional
4 bedrooms2 bathroomsSleeps 81600 sq ft
Popular amenities
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.
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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Relax & make memories on Lake Ann! Central to Traverse City/Sleeping Bear Dunes
Relax & make memories on Lake Ann! Central to Traverse City/Sleeping Bear Dunes
- Kitchen
- Washer
- Dryer
- Free WiFi
9.8 out of 10, Exceptional, (35 reviews)
House Rules
Check in after 4:00 PM
Minimum age to rent: 35
Check out before 10:00 AM
Children
Children allowed: ages 0-17
This is a family's nature paradise get away.
Events
No events allowed
Pets
Pets allowed: dogs (limit 1 total)
1 dog please. Please review with us.
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.
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
We should mention
This property does not have elevators
A car is required for transportation to and from this property
About the neighborhood
Lake Ann
Located in Lake Ann, this vacation home is in a rural area and on the beach. Village at Grand Traverse Commons and Front Street are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Lake Michigan and Sleeping Bear Dunes National Lakeshore. Traveling with kids? Consider Burnett Park, or check out an event or a game at Turtle Creek Stadium. Be sure to check out the area's animals with activities such as game walks and birdwatching.
Lake Ann, MI
What's nearby
- Bryan Lake - 19 min walk - 1.6 km
- Lake View - 3 min drive - 1.8 km
- Almira Town Hall - 4 min drive - 2.6 km
- Burnett Park - 5 min drive - 2.9 km
- Lake Ann Brewing Company - 5 min drive - 2.9 km
Getting around
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
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window9.6/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
10/10 Excellent
kimberly m.
Jul 30, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful Vintage Cottage
kimberly m.
Stayed 7 nights in Jul 2024
10/10 Excellent
jackie p.
Aug 3, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
jackie p.
Stayed 7 nights in Jul 2025
10/10 Excellent
Julie M.
Aug 16, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Thanks for the memories!
Julie M.
Stayed 7 nights in Jul 2023
10/10 Excellent
Joe M.
Jul 15, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Joe M.
Stayed 7 nights in Jun 2025
10/10 Excellent
Sue C.
Aug 5, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Absolutely wonderful!
Sue C.
Stayed 7 nights in Jul 2022
10/10 Excellent
Dave M.
Jul 15, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice location on the lake
Dave M.
Stayed 7 nights in Jul 2022
10/10 Excellent
Megan B.
Jul 5, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect Family Getaway!
Megan B.
Stayed 7 nights in Jun 2022
10/10 Excellent
Jillian M.
Sep 22, 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
The perfect spot
Jillian M.
Stayed 7 nights in Sep 2021
10/10 Excellent
Ken S.
Aug 19, 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic Getaway Retreat
Ken S.
Stayed 7 nights in Aug 2021
10/10 Excellent
Maria G C.
Jul 26, 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect in every way!
Maria G C.
Stayed 7 nights in Jul 2021
10/10 Excellent
Jeffrey R.
Jul 22, 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Such a special place!
Jeffrey R.
Stayed 14 nights in Jul 2021
10/10 Excellent
Kevin H.
Feb 17, 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
A very relaxing, comfortable place to stay. Excellent hosts!
Kevin H.
10/10 Excellent
Stephanie W., Westerville, USA
Sep 9, 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fabulous Family Vacation Spot
Stephanie W.
Stayed 7 nights in Aug 2019
10/10 Excellent
Christine P.
Aug 16, 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
Girls week
Christine P.
Stayed 7 nights in Jul 2019
About the host
Hosted by Scott Hedberg
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!
Languages:
English
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