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

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A small, single-story cabin with a porch, surrounded by a garden and trees. - Cherry Street Guesthouse with private wooded yard & firepit, 3 blocks to town! (Three Oaks)
A cozy cabin interior with a dining area, a living room with a blue sofa, and a kitchen with wooden cabinets. - Cherry Street Guesthouse with private wooded yard & firepit, 3 blocks to town! (Three Oaks)
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. - Cherry Street Guesthouse with private wooded yard & firepit, 3 blocks to town! (Three Oaks)
A gravel path leading to a small house with a white porch and a fenced yard. - Cherry Street Guesthouse with private wooded yard & firepit, 3 blocks to town! (Three Oaks)
A cozy room with a blue armchair, a pink sofa, and a wooden dining table. - Cherry Street Guesthouse with private wooded yard & firepit, 3 blocks to town! (Three Oaks)
Cherry Street Guesthouse with private wooded yard & firepit, 3 blocks to town! provides amenities, such as a firepit and a garden. Guests can connect to free in-room WiFi.

Reviews

9.4 out of 10
Exceptional

Popular amenities

  • Kitchen
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space
  • Parking available
  • Barbecue grill
The current price is £163
includes taxes & fees
8 Nov - 9 Nov

Add dates for prices

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.

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About the area

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. Visit our Three Oaks travel guide
View more Cottages in Three Oaks
Map
Three Oaks, MI

What's nearby

  • A branch with green leaves and acorns against a clear blue sky.
    The Acorn
    5 min walk - 0.3 miles
  • Vickers Theatre
    5 min walk - 0.3 miles
  • Acorn Theater
    8 min walk - 0.5 miles
  • Three Oaks Township Hall
    8 min walk - 0.5 miles
  • Watkins Memorial Park
    14 min walk - 0.8 miles

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 does it cost to stay at Cherry Street Guesthouse with private wooded yard & firepit, 3 blocks to town! ?

As of 7 Nov 2026, prices found for a 1-night stay for 2 adults at Cherry Street Guesthouse with private wooded yard & firepit, 3 blocks to town! on 8 Nov 2026 start from £163, 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 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 Sugarwood Forest Preserve are also within 3 miles (5 km).

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Reviews

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

9.4

Exceptional

9.6

Cleanliness

9.8

Location
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

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Great to walk to town. Nice area to road bike etc.
Stayed 1 night in Aug 2026
Verified review

6/10 Okay

Liked: Cleanliness, check-in, communication, listing accuracy
The only reason for three stars: the bed. All the precious reviews mentioned the bed. Certainly, I reasoned, this issue would be remedied. We slept maybe a fitful two hours because of the poor mattress quality. Sleeping on an air mattress would have been an improvement. Again, the area and the location were great. The house was adorable. But the mattress issue needs to be addressed.
Stayed 1 night in Aug 2026
Verified review

10/10 Excellent

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

Wonderful stay

Comfortable and convenient
Stayed 1 night in Jun 2024
Verified review

10/10 Excellent

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

Cute and relaxing

Super close to the main street of shops and restaurants and the cabin was cozy and comfortable.
Stayed 2 nights in Feb 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Comfortable stay and many personal touches to ensure a good experience for guests. Timely responses to questions. Would definitely stay again.
Stayed 3 nights in Jul 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

The perfect little place

Cozy little guesthouse in a quiet neighborhood. Short easy, walk to downtown restaurants and shops.
Stayed 1 night in Oct 2024
Verified review

10/10 Excellent

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

Charming Cottage in Three Oaks

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.
Stayed 1 night in Oct 2024
Verified review

10/10 Excellent

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

Cozy Cottage Near Downtown

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.
Stayed 3 nights in Oct 2024
Verified review

10/10 Excellent

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

Cozy Cottage!

This was the perfect place for us to stay during our visit to Three Oaks for a wedding. Quick walk to everything in town. Adorable cottage with everything we needed to be comfortable. Loved the art and the garden!
Stayed 3 nights in Sep 2023
Verified review

10/10 Excellent

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

Experiencing at cottage

It was a great stay. Cleanliness was top notch. Amazing stay to relax and decompress not to mention the host was very responsive and friendly. I highly recommended it!
Stayed 2 nights in Jul 2023
Verified review

10/10 Excellent

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

Great cottage for two!

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.
Stayed 2 nights in Aug 2024
Verified review

10/10 Excellent

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

Cottage delight

Wonderful atmosphere, cozy, wood lined and decorated with art. Clean and tidy as could be. Just being there put a smile on our face.
Stayed 2 nights in Mar 2025
Verified review

10/10 Excellent

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

Recommend

Clean, cozy and comfortable! Very nice neighborhood, private but close to town, would stay here again!
Stayed 4 nights in Jul 2024
Verified review

10/10 Excellent

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

Summary of our stay

Jan and Bob (the owners) met us when we were coming in. Extremely pleasant people, and the accommodations were exactly what we were seeking. Quiet, comfortable and clean. Very quaint and we would definitely stay there again.
Stayed 2 nights in Nov 2023
Verified review

10/10 Excellent

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

Cozy cottage in SW Michigan

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!
Stayed 1 night in Dec 2024
Verified review

10/10 Excellent

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

Just perfect!

The guest house was so quaint & aesthetically pleasing. Everything you need for your stay & more. Host was quick to respond from beginning to end. Very private, safe, quite neighborhood.
Stayed 2 nights in Jun 2024
Verified review

10/10 Excellent

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

Wonderful property!

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!
Stayed 1 night in Dec 2024
Verified review

10/10 Excellent

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

Perfect Little Cottage

Cute little place to stay. It was clean. Had everything we needed. Jan and Bob responded quickly to our messages. Very kind and helpful. Was a quiet place to unwind and relax. Close to everything we needed to do. Thank you for a wonderful stay.
Stayed 3 nights in Aug 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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-
Stayed 1 night in Dec 2025
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
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
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
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
Clean, private, and close to town, perfect
Stayed 2 nights in Jan 2026