Trail Side in the Heart of Winona Lake

Photo gallery for Trail Side in the Heart of Winona Lake

A house with a covered porch, a front door, and a mailbox.
A modern kitchen with white cabinets, a stainless steel refrigerator, and a wooden countertop.
A modern fireplace with a wooden facade, a mounted television above it, and a white door to the right.
A bedroom with a wooden headboard, a white bedspread, two bedside lamps, a nightstand, and a large window with frosted glass panels.
Two brown leather chairs, a small table with a lamp, and a bicycle leaning against the wall.

Reviews

9.8 out of 10
Exceptional

Highlights

  • Feels like home
    Guests love the warm, welcoming atmosphere.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Near Winona Lake

Popular amenities

  • Dog-friendly
  • Barbecue grill
  • Air conditioning
  • Refrigerator
  • Internet
  • Washer

Explore the area

View in a map
Winona Lake, IN
  • Place, Winona Lake Trails Park
    ‪1 min walk‬
  • Place, Winona Lake
    ‪3 min walk‬
  • Place, Grace College
    ‪13 min walk‬
  • Airport, Goshen, IN (GSH-Goshen Municipal)
    ‪33 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

Living Room 1

1 Double Sofa Bed

1 bathroom

Bathroom

Soap · Towels provided · Toilet · Shower only · Shampoo

Spaces

Porch or lanai
Kitchen
Number of living rooms
Outdoor play area

Add dates for prices

Similar properties

Property grounds
Stylish & Modern 2-Bdrm Apt in Downtown Warsaw featuring an urban rooftop deck.
Warsaw
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
10.0 out of 10, Exceptional, (31 reviews)
Stylish & Modern 2-Bdrm Apt in Downtown Warsaw featuring an urban rooftop deck.

About the neighborhood

Winona Lake

Located in Winona Lake, this vacation 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 mountain biking and cycling nearby.
View more Vacation Homes in Winona LakeOpens in a new window
Map
Winona Lake, IN

What's nearby

  • Winona Lake Trails Park - 1 min walk - 0.1 km
  • Winona Lake - 3 min walk - 0.3 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
  • ‪Wendy's - ‬6 min drive
  • ‪Dunkin' - ‬4 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 50 lbs per pet.

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

As of Nov 12, 2026, prices found for a 1-night stay for 2 adults at Trail Side in the Heart of Winona Lake on Nov 15, 2026 start from $219, 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?

Onsite 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?

Check-out is at 11:00 AM.

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

Situated on a lake, this vacation 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.

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 65 out of 71 reviews
Rating 8 - Good. 4 out of 71 reviews
Rating 6 - Okay. 1 out of 71 reviews
Rating 4 - Poor. 0 out of 71 reviews
Rating 2 - Terrible. 1 out of 71 reviews

10/10

Cleanliness

8.0/10

Amenities

10/10

Property conditions & facilities

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent stay!
Stayed 1 night in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very clean and nicely decorated
Stayed 1 night in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Clean, cute property with nice appointments. Lots of little touches to make it feel like home away from home. Erin was great to work with. Our stay was excellent. We would definitely stay here again!
Stayed 2 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The home was absolutely darling! We will be back.
Stayed 1 night in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The home was absolutely beautiful, freshly decorated and had every convenience I could have thought of down to coffee pods and nice shampoo, conditioner and body wash. The fireplace was an excellent bonus that took the chill out of the air quickly when we arrived. I will definitely book again.
Stayed 1 night in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house is so cute! Great location too! We had some problems with the TV’s working and Erin was easy to get ahold of & fixed them for us.Great place to stay in Winonia!
Stayed 2 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Happy with golf stay.
Stayed 1 night in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect little spot for me and my husband! Great location, very clean and comfortable! We will definitely be back to visit!
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is my second time staying at Trailside. It was chilly outside so I enjoyed the electric fireplace. Also, enjoyed the wooded view from the cozy front porch. Hiked the nearby trails & deer were visible everywhere. If I'm ever in the area again. I would definitely rent again.
Stayed 4 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent experience we will definitely stay there again
Stayed 2 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is a great place to stay. Very quiet and peaceful. We spent several hours a couple of days to read and talk on the front covered porch. It is an easy walk to the Village at Winona. Very convenient also for anyone with a college student at Grace college. We have stayed at this property 3times and it has been perfect for us.
Stayed 4 nights in Aug 2026
Response from VrboOwner on Aug 30, 2026
Thank you! We are always happy to host you guys!
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
This was my second visit to this property which should speak volumes. The first time with my husband; the second with my daughter. Erin was so easy to work with allowing early access both times. I love the proximity to the hiking and biking trails. I always love places with outdoor spaces. This one: the cozy porch and conveniently furnished patio. I encourage anyone reading my review to seriously consider this property as one of your best options.
Stayed 1 night in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wow! This place was amazing! I felt completely at home. It’s even better than the pictures show. Easily top two places I have ever stayed. Oh! And my dog loved it, too, with the trails near by.
Stayed 2 nights in Jul 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
This is a very cute little house. The neighborhood was very peaceful at night and the view of the woods across the street made it feel secluded, even though you are in Winona Lake. I would definitely recommend to anyone!
Stayed 1 night in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was perfect for our weekend stay. It was very clean and the check in & check out process were super easy!
Stayed 2 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great property would definitely stay there again! My only constructive criticism would be, All three TVs in the house have different ways of connecting to getting all the Tv apps. Multiple devices just to turn on and all different brands The toilets seat is loose. All in all a wonderful place to stay. Well appointed and a watermark for cleanliness.
Stayed 2 nights in Jul 2026
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

10/10 Excellent

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

Nice place to stay in a good area

very newly remodeled property with nice touches
Stayed 1 night in Feb 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is a fantastic property. Very clean and comfortable! Great neighborhood for walking and close to shops and restaurants. Will definitely stay here again.
Stayed 4 nights in Aug 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
Perfect place to stay. Convenient walking distance to food and shops. The house was so clean and was perfect for my husband and me. Also was convenient for going up into Amish country.
Stayed 4 nights in Oct 2025
Verified review

6/10 Okay

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice place…. Smelled like animals. It did say pet friendly and I missed it when I looked at the property.
Stayed 2 nights in Apr 2026
Response from VrboOwner on Apr 13, 2026
Thank you for your feedback! We’re glad you liked the space. While we clean thoroughly between guests, we understand sensitivities can vary. One of our guests cooked something prior to your stay that may have still been residually lingering. We’ll continue doing our best to keep the home as fresh as possible for all guests!
Tell us how we can improve our siteShare feedback