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Trail Side in the Heart of Winona Lake

Winona Lake vacation home with kitchen

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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.
A modern living room with a sofa, coffee table, and a fireplace.
A compact kitchen with white cabinets, a built-in washer and dryer, a wooden table, and a bench.
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

Entire home

2 bedrooms1 bathroomSleeps 4850 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi
  • Air conditioning

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

Room options

About the neighborhood

Winona Lake

On lake.Your stay at this Winona Lake vacation home places you within a 10-minute walk of Winona Lake Trails Park and Winona Lake. Also, Winona Lake Limitless Park is within half a mile (1 km) and Billy Sunday Home Museum is within 2 miles (3 km).
View more Vacation Homes in Winona LakeOpens in a new window

What's nearby

  • Winona Lake Trails Park - 1 min walk - 0.1 miles
  • Winona Lake - 3 min walk - 0.2 miles
  • Winona Lake Limitless Park - 5 min walk - 0.3 miles
  • Grace College - 13 min walk - 0.7 miles
  • Billy Sunday Home Museum - 13 min walk - 0.7 miles

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
  • ‪Burger King - ‬4 min drive
  • ‪Taco Bell - ‬5 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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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Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster
  • Water dispenser

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Fireplace
  • Living room

Entertainment

  • Smart TV

Outdoor areas

  • Charcoal grill
  • Firepit
  • Porch/lanai

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • One pet total (up to 50 lbs per pet)

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • No elevator (single-level property)
  • Smoking not allowed

Location highlights

  • In a village
  • Near a hospital
  • On a lake

Things to do

  • Basketball nearby
  • Fishing nearby
  • Hiking/biking trails nearby
  • Ice skating nearby
  • Kayaking nearby
  • Mountain biking nearby
  • Swimming nearby
  • Wildlife walks nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

General

  • Local artist showcase
  • Locally-owned and organized tours and activities
  • Recycling
  • Unit size: 850 square feet
  • Water dispenser

Policies

Check-in

Check-in time starts at 4:00 PM

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Check-out instructions

The host requires you complete the following before checking out:
Load and start the dishwasher
Gather used towels
Remove personal items, remove leftover food and drinks, and take out the trash
Turn off the lights and lock the doors
Failure to complete these may result in a negative review from the host.

Pets

  • Pets are welcome
  • Only dogs are allowed
  • Maximum 1 (weight limit: 50 lbs per pet)
  • Service animals are exempt from fees

Children and extra beds

  • Children are welcome.

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

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
Onsite parties or group events are strictly prohibited
Long-term renters welcome
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. Onsite parties or group events are strictly prohibited. Long-term renters welcome. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, and a deadbolt lock in each accommodation.

Frequently asked questions

How close is Trail Side in the Heart of Winona Lake to the airport?

This vacation home is 24.7 mi (37-min drive) away from the Goshen, IN (GSH-Goshen Municipal) airport, the closest popular airport to the property.

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

As of Sep 5, 2026, prices found for a 1-night stay for 2 adults at Trail Side in the Heart of Winona Lake on Sep 7, 2026 start from $249, 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.

Does Trail Side in the Heart of Winona Lake have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Trail Side in the Heart of Winona Lake to the beach?

This vacation home is 3.3 mi (8-min drive) from Pike Lake Beach.

Does Trail Side in the Heart of Winona Lake offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Trail Side in the Heart of Winona Lake?

No, there is no casino at this vacation home.

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

Check-in begins at 4:00 PM.

Is there free parking at Trail Side in the Heart of Winona Lake?

Free parking is not available at this vacation home.

Does Trail Side in the Heart of Winona Lake have a pool?

This vacation home does not have a pool.

Does Trail Side in the Heart of Winona Lake have a spa?

There are no spa services available at this vacation home.

How close is Trail Side in the Heart of Winona Lake to downtown Winona Lake?

This vacation home is 0.7 mi away from Winona Lake.

Trail Side in the Heart of Winona Lake Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 54 out of 59 reviews
Rating 8 - Good. 3 out of 59 reviews
Rating 6 - Okay. 1 out of 59 reviews
Rating 4 - Poor. 0 out of 59 reviews
Rating 2 - Terrible. 1 out of 59 reviews

10/10

Cleanliness

8.0/10

Amenities

10/10

Property conditions & facilities

Reviews

Verified review

10/10 Excellent

Nick H.

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

William S.

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

Angie A.

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

Dennis A.

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

Melissa S.

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

8/10 Good

Luann V.

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

6/10 Okay

Tracy I.

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
Verified review

10/10 Excellent

Kerry M.

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

William S.

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

Robert G.

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

Susan J.

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

10/10 Excellent

Eric B.

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

10/10 Excellent

Jesse G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice, clean, fully updated, little cottage with all amenities in a quaint little village. Perfect place to stay for our weekend getaway. Everyone we met was so friendly and polite. If staying be sure to stop at Trailhouse and rent a bike!
Stayed 2 nights in Sep 2025
Verified review

10/10 Excellent

William B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful place! So many thoughtful amenities. Comfortable, homey, welcoming. One of the best in our experience.
Stayed 2 nights in Aug 2025
Verified review

10/10 Excellent

Clay C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
I really enjoyed the location being just a block from the lake and within walking distance of parks, trails, the college, a farmer’s market and fun shops. The host had great taste and decorated the house in seasonal decor. Just right for our party of 3.
Stayed 2 nights in Oct 2025
Verified review

10/10 Excellent

Colleen J.

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

Kathie S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Spotless!! Well-appointed, comfortable furnishings and beds. Walkable location close to lake, village and walking/hiking trails.
Stayed 3 nights in Aug 2025
Verified review

10/10 Excellent

Jim M.

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

Kelly L.

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

jodi L.

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
Verified review

10/10 Excellent

David M.

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

Helen

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

Tammy B.

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

Katie D.

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

jack l.

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

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