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

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

A small, single-story cabin with a porch, surrounded by a garden and trees.
A gravel path leading to a small house with a white porch and a fenced yard.
A cozy cabin interior with a dining area, a living room with a blue sofa, and a kitchen with wooden cabinets.
A compact kitchen with wooden cabinetry, a built-in oven, and a coffee maker. A patterned rug runs along the floor, leading to a door.
A cozy room with a blue armchair, a pink sofa, and a wooden dining table.

Reviews

9.4 out of 10
Exceptional

Highlights

  • Made for relaxation
    Top-rated for comfort — guests feel right at home here.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Near The Acorn
1 bedroom1 bathroomSleeps 2

Popular amenities

  • Patio
  • Kitchenette
  • Barbecue grill
  • Air-conditioning
  • Refrigerator
  • Internet

Explore the area

View in a map
Three Oaks, MI
  • Place, Vickers Theatre
    ‪5 min walk‬
  • Place, The Acorn
    ‪5 min walk‬
  • Place, Acorn Theater
    ‪8 min walk‬
  • Airport, South Bend, IN (SBN-South Bend Intl.)
    ‪26 min drive‬

Rooms & beds

1 bedroom (sleeps 2)

Bedroom 1

1 Queen Bed

1 bathroom

Bathroom 1

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

Spaces

Deck or patio
Kitchen
Kitchenette
Garden

About this property

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

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.
Our prices include all fees. No hidden fees.

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House Rules

Check in after 4:00 PM
Check out before 11:00 AM
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Children

Adults only
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Check-out instructions

The host requires you to complete the following before checking out:
Turn off the lights and return the keys
Failure to complete these may result in a negative review from the host.

Important information

You need to know

Property # 3332866vb
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
On-site parties or group events are strictly prohibited
Long-term renters welcome
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Three Oaks

Three Oaks is home to this cottage. Vickers Theatre and Hesston Steam Museum are local landmarks, and some of the area's activities can be experienced at St. Julian Winery - Union Pier Tasting Room and Ghost Isle Brewery. Round Barn Union Pier Tasting Room and New Buffalo Railroad Museum are also worth visiting. Make sure you don't miss outdoor adventures like cycling and hiking/biking trails.
View more Cottages in Three OaksOpens in a new window
Map
Three Oaks, MI

What's nearby

  • Vickers Theatre - 5 min walk - 0.4 km
  • The Acorn - 5 min walk - 0.4 km
  • Acorn Theater - 8 min walk - 0.7 km
  • Three Oaks Township Hall - 8 min walk - 0.7 km
  • Watkins Memorial Park - 14 min walk - 1.2 km

Getting around

  • New Buffalo Station - 12 min drive
  • South Bend, IN (SBN-South Bend Intl.) - 36 min drive

Restaurants

  • ‪The Buffet at Four Winds Casino - ‬13 min drive
  • ‪Timbers at Four Winds Casino - ‬15 min drive
  • ‪Ray & Al’s - ‬10 min drive
  • ‪Heston Supper Club - ‬13 min drive
  • ‪Journeyman Distillery - ‬5 min walk

Frequently asked questions

Is Cherry Street Guesthouse with private wooded yard & firepit, 3 blocks to town! pet-friendly?

No, pets are not allowed at this property.

How much is parking at Cherry Street Guesthouse with private wooded yard & firepit, 3 blocks to town! ?

On-site parking is available at the property.

What time is check-in at Cherry Street Guesthouse with private wooded yard & firepit, 3 blocks to town! ?

Check-in begins at 4:00 PM.

What time is check-out at Cherry Street Guesthouse with private wooded yard & firepit, 3 blocks to town! ?

Checkout is at 11:00 AM.

Where is Cherry Street Guesthouse with private wooded yard & firepit, 3 blocks to town! located?

Situated in Three Oaks, this cottage is within a 10-minute walk of The Acorn, Vickers Theatre and Three Oaks Township Hall. Acorn Theater and Watkins Memorial Park are also within 1 mile (2 km).

Reviews

9.4

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 66 out of 83 reviews
Rating 8 - Good. 10 out of 83 reviews
Rating 6 - Okay. 3 out of 83 reviews
Rating 4 - Poor. 2 out of 83 reviews
Rating 2 - Terrible. 2 out of 83 reviews

9.6/10

Cleanliness

10/10

Check-in

9.8/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great stay in Three Oaks! This property was beautiful and in a great location. The house felt very cozy and private. I would absolutely recommend this rental!
Stayed 3 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Bike rental shop nearby.
Stayed 1 night in Aug 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Cute little property close to town. The only thing keeping it from 5 stars is the mattress. It is one of those where you and your spouse are going to sink to the center of the bed despite your best efforts! :)
Stayed 3 nights in Sep 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Overall I enjoyed my stay, great comms from the hosts and the place was easy to find. The place is clean, cozy and the porch works well for chillin outside. There’s really no HVAC to speak of but I stayed on a cool evening so no biggie. The only wrinkles with the stay were the too soft (foam?) mattress, no tvs, and a loose toilet. Otherwise it’s a nice place in a good location that’s easily walkable downtown.
Stayed 1 night in Sep 2026
Response from VrboOwner on 12 Oct 2026
Hi Richard, thank you for your review. There definitely is a/c in a wall unit covered by a red grate. Sorry you didn't see it. Tv is not listed as an amenity, as many guests prefer the "cabin" in the woods atmosphere & the quiet privacy. Thanks for pointing out the bed & loose item, they have been taken care of. Thanks again. Jan & Bob
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place. Close to downtown Three Oaks which is a fantastic gem in SW Michigan. Highly recommend this for a couple visiting the area.
Stayed 1 night in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved our one-day stay at the Cherry Street Guest House. It was charming, secluded, surprisingly roomy, with no clutter, and spotlessly clean. An excellent bathroom and kitchenette, comfortable bed, very pleasant area for sitting and dining, and great outdoor space (with grill and fire pit). The décor is tasteful and unfussy, the wood panelling welcoming. A short walk and even shorter drive to the centre of Three Oaks (we enthusiastically recommend Journeyman Distillery -- a very good tour, great products, nice restaurant, and a very enjoyable putting course). We loved the town and the Guest House and would stay again without hesitation.
Stayed 1 night in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
A charming little place, perfect for two people for a get away.
Stayed 1 night in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great communication from our host and excellent location
Stayed 3 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Clean great place for 2 people.
Stayed 2 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very cute place close to the acorn. We will book again! Thanks for hosting us!
Stayed 1 night in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Clean, private, and close to town, perfect
Stayed 2 nights in Jan 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We typically like to stay in secluded out of town locations, but wanted to give this a try. It was cute and very clean inside. It was very quite at night so no problem with noise. Jan and Bob were great! Would definitely stay again!
Stayed 2 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Cute place in a great location!
Stayed 1 night in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location and easy check in/out.
Stayed 3 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was great. Excellent hosts!
Stayed 1 night in Jan 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 1 night in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very Clean and cozy. Really close to Journeyman and Acorn. Nice quiet area.
Stayed 2 nights in Mar 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very cute. Good for two people.
Stayed 1 night in Mar 2026
Verified review

2/10 Terrible

Liked: Cleanliness, check-in, communication, location
Property was horrible . Too many bad things to mention and no tv .
Stayed 8 nights in Jun 2026
Verified review

6/10 Okay

Liked: Check-in, location
Disliked: Cleanliness
Clean enough. Bathroom & shower unappealing. Ground outside a mess. A/C did not work with remote - had to unplug & plug back in. No TV but that was not an issue for us. Nice walking distance to town. Left day early.
Stayed 2 nights in Jun 2026
Response from VrboOwner on 12 Jul 2026
Our guesthouse is always spotless when a guest checks in. I suppose that makes it sufficient. As to the outside ground conditions, we lost a tree in a recent storm & was in the process of being removed. This does not affect access & the grounds are always well maintained. The full bathroom which includes a toilet, sink & walk in shower as well as great lighting, vanity & full length mirrors & built in shelving for towels & supplies is attractive & efficient. The a/c remote needed new batteries. We would have addressed this if you had contacted us. Even tho you acknowledged the lack of tv was not an issue, you clearly knew that when you read the amenity list & subsequently reserved the property. Apparently, your early exit had nothing to do with the guesthouse. Your ambiguous and innaccurate review as well as any communication whatsoever causes us to question your desirability as a guest.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
very well appointed clean and very near the main drag . Will not hesitate to stay there again
Stayed 1 night in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 1 night in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 1 night in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 2 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 1 night in Nov 2025

About the host

Hosted by Jan or Bob

Host profile image
We moved to Three Oaks 6 years ago. We love this community & have watched it grow as an even larger artist's center! Having been involved in real estate & law, we are now retired but involved in all the Village has to offer including art as Bob is an oil painter & furniture maker known as "Vincent".

Why they chose this property

The location is 3 short blocks to town on a half acre. We love the convenience yet quiet privacy. Shopping & dining is great with lots of galleries, unique shops, great restaurants, bakeries, wineries, breweries, a distillery & coffee shops!. Local farms & fruitstands provide a wide array of meats, produce, cheeses & homemade breads.

What makes this property unique

As great reviews indicate, we have a darling cozy & private guesthouse with everything you need. It's on the opposite side of a 1 acre lot, with trees, privacy & quiet, has it's own driveway & a firepit! It's so close to town, shops, restaurants, wedding venues, bike rental & trails, hiking & of course, Lake Michigan beaches & Warren Dunes just 10 minutes away with kayaking rentals on the river!

Languages:

English

Premier Host

They consistently provide great experiences for their guests
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