Cherry Street Guesthouse with private wooded yard & firepit, 3 blocks to town!

Three Oaks, Michigan
$280 avg/night
Bed 1

Bed

Bath 1

Bath

Home Cottage

Property Type

Sleep 2

Max Sleeps

A romantic getaway in a private wooded setting in the charming Village of Three Oaks sits in a secluded corner of a large lot with privacy fencing & its own driveway. This one bedroom cottage has vaulted ceilings & pine interior and was designed with a northwoods flair by local artist & owner Vincent. It contains several of his paintings & custom designed furniture.

Only a 3 block walk to downtown Three Oaks, Journeyman's Distillery & Froelich's shops, restaurant, bakery/ coffeehouse, candy shop & wedding venue as well as a farmers' market, wonderful restaurants, unique shops, art galleries, a fine arts cinema, and a live performance theater, 2 major wedding venues and an organic distillery with world class putting greens designed after St. Andrews golf course in Scotland.

Beaches, Warren Dunes, kayaking, biking, hiking, wineries, breweries & all that Harbor Country has to offer are nearby.

Read More Expand
  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    1 Bedroom Bed Sheets Provided
  • GENERAL

    Property Does Not Allow Children Unit Size: 400 Sq Ft (37 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Electric Kettle Ice Maker Microwave Paper Towels Refrigerator Stovetop
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Barbecue Grill Firepit Garden Outdoor Furniture Patio
  • BATHROOMS

    1 Bathroom Bathtub Or Shower Hair Dryer Shampoo Soap Toilet Paper Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Bicycle On Site Cycling Nearby Hiking Nearby Hiking/biking Trails Nearby
  • CLIMATE CONTROL

    Air Conditioning Heating
  • SERVICES AND CONVENIENCES

    Phone
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 2

Map Map

School District Availability

Review Review

  • Tina B.

    Submitted Apr 20, 2026

    Stayed Apr 18, 2026

    We had a lovely time at this little cabin for just an overnight stay. We appreciated that we were able to do one night during the off season. It was the perfect little cabin for what we needed. The owners were great with communication and instructions. It is so close to the town and we enjoyed the Journeyman whiskey distillery with Glenn as our tour guide and had the Granor Farm dinner experience and it was fabulous! We shopped Three Oaks shops on Sunday and stopped at the Warren Dunes and in New Buffalo at Beer Church for amazing pizza on the way home. Overall relaxing and fun 20th anniversary celebration.

  • Shirley C.

    Submitted Mar 28, 2026

    Stayed Mar 27, 2026

    Very cute. Good for two people.

  • Bob L.

    Submitted Mar 23, 2026

    Stayed Mar 20, 2026

    Very Clean and cozy. Really close to Journeyman and Acorn. Nice quiet area.

  • Jason P.

    Submitted Mar 12, 2026

    Stayed Feb 20, 2026

    Clean great place for 2 people.

  • Kaleigh A.

    Submitted Mar 1, 2026

    Stayed Feb 28, 2026

    A charming little place, perfect for two people for a get away.

  • Melissa M.

    Submitted Feb 28, 2026

    Stayed Feb 27, 2026

    The Guesthouse was a perfect place for an overnight stay in Three Oaks. We were within walking distance of restaurants and the theater where we were seeing a concert.

  • Submitted Feb 20, 2026

    Stayed Jan 23, 2026

    Everything was great. Excellent hosts!

  • Rebecca L.

    Submitted Feb 20, 2026

    Stayed Feb 13, 2026

    Great communication from our host and excellent location

  • Dorea L.

    Submitted Jan 12, 2026

    Stayed Dec 31, 2025

    This is such a great place! The cabin is amazingly cute, obviously curated by an artist with great hospitality skills. We only stayed one night, just in for a show at The Acorn Theater. It was cold and icy but the cabin is just a couple block walk. Had it been summer we would have. We also would have taken advantage of the fire pit in the garden which I’m quite sure is spectacular in season. Garden is again filled with art. Bob is a very good host, attentive to our asks and needs. And he has good recommendations for local eateries! We have already booked a return stay for August when we can enjoy all Cherry Street Guesthouse has to offer. Thanks Bob!!! Cozy AClean ALocation AHospitality AWeather D-

  • Alex P.

    Submitted Jan 7, 2026

    Stayed Jan 2, 2026

    Clean, private, and close to town, perfect

  • Alison H.

    Submitted Dec 5, 2025

    Stayed Nov 23, 2025

    Cute place in a great location!

  • Michaele J.

    Submitted Nov 30, 2025

    Stayed Nov 26, 2025

    The main reason for two stars is that the primary piece of furniture traditionally used for relaxation in the living area was an extremely uncomfortable futon which was supposed to act as a sofa. We tried laying it flat and adding pillows to try to make it more comfortable but, alas, no luck. Besides the futon was one other chair for relaxing. There’s no TV so we brought our own setup to watch the game. There are no cooking utensils except for one metal spatula! I was lucky I brought a large spoon from home! There were no bowls so we ate out ice cream from coffee mugs. Aside from one small saucepan, the cooking pans were a pair of very thin pans which scorched the food and had no lids. We couldn’t open our canned food as there was no can opener and no dish drainer to dry dishes. also no bedside lights for reading.

  • Carl S.

    Submitted Nov 24, 2025

    Stayed Nov 22, 2025

    The house was perfect for our honeymoon night. Comfortable and nicely stocked with towels, soap, glassware, mini fridge, coffee and separate tea maker.Quent small Southwestern Michigan town!

  • Linda C.

    Submitted Oct 9, 2025

    Stayed Oct 8, 2025

    Perfect cozy spot for two people to stay while checking out Three Oaks and Warren Woods. The hiking was beautiful. Bed was comfortable and the kitchen had everything we needed for our trip. Enjoyed the cozy feel of the tiny cabin home and the outdoor seating was nice. Would stay again.

  • Krista S.

    Submitted Sep 28, 2025

    Stayed Sep 26, 2025

    We came to Three Oaks for a friend’s wedding and had the absolute best time! Jan and Bob’s guest house is lovely and very comfortable. You will not regret spending a few days here.

  • Ryan F.

    Submitted Sep 18, 2025

    Stayed Sep 5, 2025

    Very nice and clean

  • Amanda A.

    Submitted Aug 11, 2025

    Stayed Jul 24, 2025

    Great location and easy check in/out.

  • Nick B.

    Submitted Aug 2, 2025

    Stayed Jul 30, 2025

    Great 2 night stay! Firepit was awesome to use at night. 10/10 recommend.

  • Nicole S.

    Submitted Jul 28, 2025

    Stayed Jul 27, 2025

    Cute, clean, functional! Fire pit was nice to enjoy at night.

  • Linda C.

    Submitted Jul 28, 2025

    Stayed Jul 20, 2025

    Clean, walking distance to town and close to neighboring cities. Never met the owners but had to contact them once and the quickly responded. Only one thing, there is a window air conditioner in the main room which also has a ceiling paddle fan. Got a litle warm in the bedroom. A ceiling fan would help.We had a great time.

  • Barbara B.

    Submitted Jul 26, 2025

    Stayed Jul 3, 2025

    Comfortable stay and many personal touches to ensure a good experience for guests. Timely responses to questions. Would definitely stay again.

  • michael m.

    Submitted Jun 14, 2025

    Stayed Jun 13, 2025

    very well appointed clean and very near the main drag . Will not hesitate to stay there again

  • Submitted Jun 8, 2025

    Stayed Jun 4, 2025

    The property is lovely and just right for 2 people. My husbans was disappointed that there was not a TV bit we were so busy I did not notice. The artwork in the space is beautiful and gives an eclectic vibe. Super convenient to everything.

  • Shelia M.

    Submitted Jun 1, 2025

    Stayed May 30, 2025

    Cozy and clean place to stay in a great location!! Loved sitting by the fire. Lots of extra blankets, a fan, and an electric fireplace. We will come back!

  • Kathleen G.

    Submitted May 19, 2025

    Stayed May 16, 2025

    Very cute cottage. Great for 2 people. Super clean. No TV. (We didn't care).Could use some blackout curtains in the bedroom, especially after a wedding ;)

  • Greta S.

    Submitted Apr 28, 2025

    Stayed Apr 18, 2025

    The cottage is adorably decorated and spotlessly clean. I recommend taking a fan for the bedroom if that is your norm.

  • Mary F.

    Submitted Apr 14, 2025

    Stayed Apr 11, 2025

    This is a nice place for a person or couple to stay in a quiet neighborhood setting within easy walking distance to all the charms of Three Oaks MI. We would have loved to give this cottage a 10 rating, but the issues preventing that are the unfortunate “sulfur/rotten egg” smell when running the water in the kitchen and bathroom sinks (we did not risk showering) and we found the mattress a bit too soft/sloping to the middle for our preference. Also my husband noted the lack of any ventilation in the bathroom.

  • Submitted Mar 30, 2025

    Stayed Mar 29, 2025

    This little place is in a very convenient spot. I should have asked questions, since this was my first VRBO stay. I didn’t realize there wouldn’t be a tv or sugar/creamer for coffee. We enjoyed our stay!

  • Gregory G.

    Submitted Mar 23, 2025

    Stayed Mar 20, 2025

    Wonderful atmosphere, cozy, wood lined and decorated with art. Clean and tidy as could be. Just being there put a smile on our face.

  • Janice G.

    Submitted Mar 8, 2025

    Stayed Mar 1, 2025

    The place was clean and cute. We stayed one night to see a concert at the Acorn, which was just a few blocks away. It should be listed in the description that there isn’t a TV. It’s not listed on the amenities, but generally it’s a given that there is a TV! That was our only disappointment.

  • Lexi G.

    Submitted Feb 28, 2025

    Stayed Feb 21, 2025

    Super close to the main street of shops and restaurants and the cabin was cozy and comfortable.

  • julie g.

    Submitted Feb 16, 2025

    Stayed Feb 14, 2025

    Wonderful little cottage for a weekend get away! Thank you!

  • Sandy H.

    Submitted Dec 23, 2024

    Stayed Dec 20, 2024

    We came up to see the IU vs ND game, but this place ended up being the best part of the trip. Cottage was cute as a button and a short drive from the stadium. We were bummed we missed the Prancer festivities but were still able to enjoy the towns self-guided tour of the making of Prancer. Will come back next year for sure!

  • Valerie B.

    Submitted Dec 23, 2024

    Stayed Dec 21, 2024

    What an adorable and comfortable cottage! The gracious and friendly hosts were available and accomodating. They provided many recommendations for dining and entertainment in the area. Cabin in the woods feel, but conveniently in town. Definitely would return!

  • Brandi H.

    Submitted Nov 28, 2024

    Stayed Nov 15, 2024

    Stayed here for a girls birthday weekend. Cute place for two people. Would definitely stay there again!

  • Brent C.

    Submitted Nov 2, 2024

    Stayed Nov 1, 2024

    Fantastic charming tiny house. We will be staying here again if the opportunity arises.

  • C B.

    Submitted Oct 26, 2024

    Stayed Oct 17, 2024

    Charming, quirky cottage in Three Oaks - walking distance to all the shops and restaurants. Loved the colorful decor and cool artwork and all the basics were provided for a comfortable stay. Good place for a solo traveler or couple.

  • Alisa K.

    Submitted Oct 23, 2024

    Stayed Oct 18, 2024

    Cute cottage near downtown area of Three Oaks. The property owners were very helpful and accommodating during our stay. This is a great location and it has all of the basic essentials except for a tv.

  • HAROLD C.

    Submitted Oct 18, 2024

    Stayed Oct 16, 2024

    Cozy little guesthouse in a quiet neighborhood. Short easy, walk to downtown restaurants and shops.

  • Erika L.

    Submitted Sep 20, 2024

    Stayed Sep 17, 2024

    Very cozy, charming, and pristine cottage that’s only a couple of blocks from downtown Three Oaks. Perfect for my solo stay!

  • Bradley G.

    Submitted Sep 2, 2024

    Stayed Aug 31, 2024

    Great cottage! Perfect for two. Super clean and comfortable. Walk to town for breakfast lunch or dinner! Close to Union Pier, New Buffalo, and lots of activities in the area.

  • John L.

    Submitted Aug 22, 2024

    Stayed Aug 19, 2024

    We enjoyed two nights and wall was well. Nice and simple, yet artistic. Place is a great get away!

  • Jennifer P.

    Submitted Aug 5, 2024

    Stayed Jul 22, 2024

    This Three Oaks location is likely best if taking advantage of prime weekday/weekend town events and community business hours. Fortunately, New Buffalo and neighboring towns are a close drive to access coffee and activities. Offered a few suggestions to owners that would allow future guests a 10/10 experience.

  • Leo P.

    Submitted Aug 5, 2024

    Stayed Jul 11, 2024

    A quaint and cozy stay. Loved it. Hope to be back.

  • Jennifer E.

    Submitted Jul 23, 2024

    Stayed Jul 21, 2024

    Perfect cozy cabin for a short getaway!

  • Alicia Y.

    Submitted Jul 22, 2024

    Stayed Jul 7, 2024

    Clean, cozy and comfortable! Very nice neighborhood, private but close to town, would stay here again!

Your dates are Available!

Total

Includes taxes and fees
$280+
View details