Entire home·Private host

Trail Side in the Heart of Winona Lake

Photo gallery for Trail Side in the Heart of Winona Lake

A covered porch with wooden flooring, two chairs, a table, and a window with blinds. - Trail Side in the Heart of Winona Lake (Winona Lake)
A compact kitchen with white cabinets, a built-in washer and dryer, a wooden table, and a bench. - Trail Side in the Heart of Winona Lake (Winona Lake)
A living room with a sofa, coffee table, and a TV mounted on a wooden wall. - Trail Side in the Heart of Winona Lake (Winona Lake)
Two brown leather chairs, a small table with a lamp, and a bicycle leaning against the wall. - Trail Side in the Heart of Winona Lake (Winona Lake)
A bedroom with a wooden headboard, a white bedspread, two bedside lamps, a nightstand, and a large window with frosted glass panels. - Trail Side in the Heart of Winona Lake (Winona Lake)
At Trail Side in the Heart of Winona Lake, you can look forward to a firepit, a playground and laundry facilities. Stay connected with free in-room WiFi.

Reviews

9.8 out of 10
Exceptional

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Free Wi-Fi
  • Air-conditioning
The current price is €243
includes taxes & fees
25 Oct - 26 Oct

Add dates for prices

About this property

Trail Side in the Heart of Winona Lake

  • In the heart of beautiful Winona Lake & just steps from the acclaimed trail system & greenway, this home offers a great getaway for any occasion! Take a short walk to the Village in Winona to enjoy dining, coffee, ice cream, shops, splash pad & park, & the beach. Our home celebrates the unique culture Winona Lake offers - trails, biking, lake life, the village, and Midwest charm!

    Enjoy this peaceful location with 2 bedrooms and a sofa bed, an open concept kitchen/ living room, fireplace, space for entertaining outdoors, and a gas fire pit on the cozy but expansive front porch that overlooks a wooded area. The open-concept living room & eat-in kitchen pairs space for dining & a comfortable sitting area with a TV & electric fireplace. The kitchen is fully stocked for your cooking and dining needs. Take your dinner outdoors to the quiet dining area with a gas and charcoal grill available and enjoy the birds and sounds of Winona Lake.

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About the area

Located in Winona Lake, this holiday home is on a lake. The area's natural beauty can be seen at Oppenheim Woods and Winona Lake Trails Park, while Billy Sunday Home Museum and Wagon Wheel Theatre are cultural highlights. Kayaking and fishing offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking and mountain biking nearby. Visit our Winona Lake travel guide
View more Holiday homes in Winona Lake
Map
Winona Lake, IN

What's nearby

  • A water tower, a lake, and a residential area with houses and trees.
    Winona Lake
    3 min walk - 0.3 km
  • Winona Lake Trails Park
    1 min walk - 0.1 km
  • Winona Lake Limitless Park
    5 min walk - 0.4 km
  • Grace College
    13 min walk - 1.1 km
  • Billy Sunday Home Museum
    13 min walk - 1.1 km

Getting around

  • Goshen, IN (GSH-Goshen Municipal)
    37 min drive

Restaurants

  • McDonald's
    6 min drive
  • Do Good BBQ
    4 min drive
  • Dunkin'
    4 min drive
  • Taco Bell
    5 min drive
  • Burger King
    4 min drive

Frequently asked questions

Is Trail Side in the Heart of Winona Lake pet-friendly?

Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 23 kg per pet.

How much does it cost to stay at Trail Side in the Heart of Winona Lake?

As of 24 Oct 2026, prices found for a 1-night stay for 2 adults at Trail Side in the Heart of Winona Lake on 25 Oct 2026 start from €243, 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 Trail Side in the Heart of Winona Lake?

On-site parking is available at the property.

What time is check-in at Trail Side in the Heart of Winona Lake?

Check-in begins at 4:00 PM.

What time is check-out at Trail Side in the Heart of Winona Lake?

Checkout is at 11:00 AM.

Where is Trail Side in the Heart of Winona Lake located?

Situated on a lake, this holiday home is within a 10-minute walk of Winona Lake Trails Park, Winona Lake and Winona Lake Limitless Park. Billy Sunday Home Museum and Grace College are also within 15 minutes.

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Reviews

Trail Side in the Heart of Winona Lake Reviews

9.8

Exceptional

10

Cleanliness

10

Location

10

Property conditions & facilities
Rating 10 - Excellent. 63 out of 69 reviews
Rating 8 - Good. 4 out of 69 reviews
Rating 6 - Okay. 1 out of 69 reviews
Rating 4 - Poor. 0 out of 69 reviews
Rating 2 - Terrible. 1 out of 69 reviews

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Fabulous place to stay! Great location, easily accessible to anything you need or want to see in Winona Lake and surrounding areas. The house very clean and comfortable and safe. Thank you, had a wonderful time.
Stayed 2 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent location and a very comfortable home. Would stay again.
Stayed 5 nights in Feb 2026
Verified review

10/10 Excellent

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

Great place to stay

House very comfortable, we enjoyed being close to the trails
Stayed 3 nights in Feb 2025
Verified review

10/10 Excellent

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

Great location; clean home

Perfect location for the lake and the trails. Would stay here again
Stayed 2 nights in Apr 2025
Verified review

10/10 Excellent

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

Weekend Stay

Very clean, well appointed bungalow in a great location.We would definitely return when visiting the area again.
Stayed 2 nights in Mar 2025
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is the second time I have stayed at this delightful lake cottage in the woods and I hope to return next year! I stayed almost 2 weeks to work on a writing project - perfect for that. The location is ideal - turn left out the front door and you are on your way to forest trails, turn right and you are off to the lake and village! The host is very responsive and the home so welcoming. The only reason I did four stars instead of five is due to a few home upkeep items I mentioned to the host.
Stayed 12 nights in May 2026
Verified review

10/10 Excellent

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

Lovely little cottage near bike trail

Great location for bike trail, lovely accommodations for our visit here to see family; gracious host.
Stayed 6 nights in Aug 2024
Verified review

10/10 Excellent

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

Fall getaway

Last minute getaway to the beautiful fall foliage. Couldn’t have asked for a better area or Accommodations to stay in.
Stayed 1 night in Oct 2024
Verified review

10/10 Excellent

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

Great spot!

Stayed here for an ND weekend. Two bedroom was perfect for my older parents and I, plus it was pet friendly and my dog loved the walking trails.
Stayed 3 nights in Nov 2024
Verified review

10/10 Excellent

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

Great house in a great location

The house was very clean, comfortable and recently updated. Awesome location near the lake, walking and mountain bike paths. We'd definitely go again!
Stayed 2 nights in May 2024
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
So clean and so well decorated. We loved biking the trails and around the town. It was perfect for our needs. Definitely plan to stay again.
Stayed 8 nights in Jun 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is an immaculate home. It is very close to some nice trails. It is close to the park at Winona Lake, who’s is a GREAT park with a splash pad, pickle ball and tennis courts, a nice playground and even a sandy beach area. The kitchen is really well stocked. A roomy 2 bedroom. Great place to stay.
Stayed 1 night in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Such a relaxing view of the woods across the street. Loved hearing all the wildlife. Enjoyed hiking the nearby woods. Close proximity to Winona Lake where we enjoyed a beautiful sunset. The house was very comfortable & relaxing. I would definitely rent again.
Stayed 4 nights in Sep 2025
Verified review

10/10 Excellent

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

Cute and Comfortable!

Loved the fireplace. Great property for 4 sisters trip. Very clean and updated. Nice neighborhood. Will book again.
Stayed 1 night in Dec 2024
Verified review

10/10 Excellent

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

Perfect Getaway

My husband and I very much enjoyed our stay. The home was peaceful, comfortable and clean. We loved the front porch and the propane fire pit there. The proximity to the trails, lake and shoppes made it easy for us to take advantage of all of them. It was everything we wanted.
Stayed 3 nights in Sep 2024
Verified review

10/10 Excellent

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

Annual changing of the leaves weekend with friends

Wonderful, clean and lovely combinations. We are thinking of coming back each year!
Stayed 4 nights in Oct 2024
Verified review

10/10 Excellent

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

Very nice 2 bedroom

Very clean and beautiful 2 bedroom home. Close to all of the best activities in Winona Lake. Everything was brand new!
Stayed 2 nights in Aug 2024
Verified review

10/10 Excellent

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

Fall in Winona

The property is very comfortable and quiet within easy walking distance of the shops in Winona. Everything was beautiful and casual and brand new. Our stay was too short and we look forward to returning.
Stayed 3 nights in Oct 2024
Verified review

10/10 Excellent

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

Beautiful rustic cottage

We had an amazing stay. Great location. Walking trails next door. Walking distance to stores and lake. Beautifully decorated home. Very clean and new. Had an amazing porch and fire pit. This home was spectacular! Would stay again and again.
Stayed 2 nights in Sep 2024
Verified review

10/10 Excellent

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

Perfect Little Getaway in our Hometown

My fiancé and I used to live in Warsaw before moving to Iowa and we enjoyed visiting Winona Lake and the Village. We have 2 dogs who we love to take on the trails for the exercise and the beautiful scenery. Having this cozy home for us and our dogs to relax at while moving my mother in Warsaw over the weekend was wonderful. We will absolutely want to come back to enjoy this home-away-from-home again!
Stayed 2 nights in May 2024
Verified review

8/10 Good

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

Positive

Overall it was a wonderful experience. It was our first time using a vacation rental. Erin responded quickly when I experience small inconveniences related to the comfort of our stay. As a family we enjoyed the fireplaces and the short walk to the park!
Stayed 14 nights in Oct 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Winona Lake was a gem. It was the perfect town for our little get away. Boutique stores, trails and history, great food (can recommend River coffee shop) and Oak and Alley restaurant (Warsaw). Pottery store holds classes. And the wagon Wheel theatre held their youth production. Amazing talent. The Trailside BNB was the perfect venue for our stay. The owners made you feel very welcome. The little touches - brochures, games, and so much more made our stay feel spa like. Clean and cozy. We both enjoyed the front porch and the propane fireplace, in the chilly fall evening. Many thanks to our hosts We hope to come back, again.
Stayed 2 nights in Oct 2025
Verified review

10/10 Excellent

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

Location Qualit Outstanding!

This was a perfect cottage experience - the house itself is so charming and well kept but what puts it over the top is the location! It is literally minutes from the wonderful forest trails or the lake. You can't go wrong with a walk in either direction! And it is an easy walk to the beach park and Village! I stayed two weeks to work on a writing project and could have stayed longer. Two of my favorite features of the house are the electric fireplace indoors and the gas fire pit on the porch. And the fact that they welcome dogs is a wonderful accommodation. All communication was fast and responsive to help with some issues that needed attention. I hope to return!
Stayed 14 nights in Apr 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Charming and immaculate, this 2 bedroom property had everything we needed and was perfect for our family. It's conveniently located just a short walk from a public beach, coffee shop, ice cream shop, restaurant and shopping on Winona Lake. The owner was friendly and responsive. We enjoyed evenings on the front porch and used the gas grill to cook dinner one night. The property is equipped with a washer and dryer, beach towels, and several board/card games as well. Highly recommend!
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great time here. Very relaxing and quiet. The house is very comfortable and convenient. Winona Lake is a very friendly town. Great place to spend July 4th.
Stayed 2 nights in Jul 2026