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 Aug 23, 2025, prices found for a 1-night stay for 2 adults at Trail Side in the Heart of Winona Lake on Aug 27, 2025 start from CA $168.96, excluding 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.

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.

Trail Side in the Heart of Winona Lake - Latest Reviews, Deals & Photos 2025

About the area

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 hiking/biking trails and cycling nearby.

Visit our Winona Lake travel guide

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10/10 Excellent

Dennis A.

Feb 25, 2025

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

10/10 Excellent

Kerry M.

Apr 13, 2025

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

10/10 Excellent

William S.

Mar 30, 2025

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

10/10 Excellent

Jim M.

Nov 21, 2024

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

10/10 Excellent

jodi L.

Dec 11, 2024

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

Winona stay

Loved the house and the location. Everything was perfect for our stay. Can’t wait to try it in the summer

Stayed 4 nights in Nov 2024

10/10 Excellent

Colleen J.

Aug 18, 2024

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

10/10 Excellent

Kelly L.

Nov 11, 2024

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

10/10 Excellent

Sandy A.

Dec 10, 2024

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

10/10 Excellent

David M.

May 28, 2024

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

10/10 Excellent

Sue K.

Aug 30, 2024

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

Girl's Trip

The house was perfect for my friend and I. The front porch was our favorite spot.

Stayed 1 night in Aug 2024

10/10 Excellent

Calvin J.

Oct 30, 2024

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

10/10 Excellent

Pamela B.

Sep 7, 2024

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

10/10 Excellent

Luann V.

May 15, 2025

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

10/10 Excellent

Shwrry C.

Jul 16, 2024

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

Charming and Perfect!

The place was beautifully designed and decorated. In great shape, newly renovated. They thought of everything we could possibly need! Great quality and will return again and again!

Stayed 2 nights in Jul 2024

10/10 Excellent

Mike S.

Aug 7, 2024

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

10/10 Excellent

Laurie R.

Sep 24, 2024

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

8/10 Good

Parthenia M.

Oct 30, 2024

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

10/10 Excellent

Janette G.

May 19, 2024

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

10/10 Excellent

Robert G.

Feb 19, 2025

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

10/10 Excellent

Lucy S.

Oct 27, 2024

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

10/10 Excellent

Bob B.

Sep 15, 2024

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

Stayed 3 nights in Aug 2024

10/10 Excellent

jack l.

Jul 24, 2024

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

Excellent property

Perfect stay for a getaway to Winona Lake. Place was beautiful and had everything we needed. The owner Erin was extremely nice. Thanks!

Stayed 4 nights in Jul 2024

10/10 Excellent

Helen

Jun 27, 2024

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

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Trail Side in the Heart of Winona Lake

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