Vacation rentals in Winkler

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Top-rated vacation rentals in Winkler

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Guest favorite
A winter view of Mosswood Cabin is presented, showcasing a wooden structure adorned with a sloped roof and a large front deck. Snow blankets the ground and roof, while trees with bare branches frame the cozy entrance and screened porch area.
Cabin in Roseisle
4.99 out of 5 average rating, 173 reviews

Mosswood Cabin - on the Manitoba Escarpment

Mosswood Cabin is a cozy (hygge, gezellig) 700 sq ft year-round cabin located on the Manitoba Escarpment. 8000 years ago, it was lakefront property on Glacial Lake Agassiz, now it’s 40 acres of gorgeous parkland forest, with a seasonal creek winding its way through a deep ravine, access to many kilometres of multi-use trails, and part of a regular raptor, songbird, and monarch migratory route. The cabin is equipped with a full kitchen, a bathroom, a wood stove, and an outbuilding electric sauna.

Guest favorite
Apartment in Winkler
5 out of 5 average rating, 12 reviews

Studio 7 – Mighty, Modern, Fully Equipped

Small but mighty, this compact Winkler suite offers style, convenience and the perfect balance for your stay. This cozy studio is thoughtfully designed to offer everything you need for a relaxing stay, all within a clean, modern, and intelligently organized layout. What You’ll Love: ✔ Private entrance, self-contained suite — no shared living spaces ✔ 3-Piece Bath ✔ Fully Equipped Kitchenette ✔ Mini Fridge/freezer ✔ Queen-Size Bed ✔ Smart TV ✔ Modern Lighting & Clean Design ✔ Convenient Location

Top guest favorite
A modern loft is perched above a two-car garage, featuring a spacious balcony with glass railing. The exterior is complemented by a neatly maintained lawn and a single small tree. Clear skies provide a bright backdrop, highlighting the architectural simplicity of the building.
Home in Winkler
4.98 out of 5 average rating, 154 reviews

Loft on Small Acreage in Winkler, Morden area.

Pine Loft is set on a beautiful 2 acre yard which features a large garden with a range of fruits and vegetables that we welcome you to help yourselves to! You can enjoy sitting on the balcony while the sun sets across the expansive prairie sky over picturesque fields characteristic to Southern MB. Located on the outskirts of Winkler you will have close access to everything Winkler and the area has to offer while being able to experience privacy with a little taste of the Manitoban countryside.

Top guest favorite
The exterior of The Red Granary is showcased, featuring a vibrant red façade and green doors. A porch with seating is visible, along with a gravel pathway leading to the entrance. Lush greenery surrounds the building, enhancing the serene setting.
Barn in Neubergthal
4.99 out of 5 average rating, 154 reviews

A peaceful , Quiet farmyard in a historic granary

A quiet farmyard. It is situated half mile North of Neubergthal-a national Heritage site. The Red Granary was a building used for storing grain, and it was red and it had green doors. It is an original style from the early 1900’s We live on the same farmyard with 4 dogs and farm animals. But we each have our own space. Whether a guest wants to interact or wants privacy, both are easily attainable and respected. You MUST register your dog as a guest. (Dogs cannot be left alone in the Granary)

Top guest favorite
Tiny home in Morden
5 out of 5 average rating, 28 reviews

Valley Tiny!

Come to the Valley Tiny where you can leave behind the hustle and bustle of everyday life. Experience God's creation in an unforgettable setting. Small, simple, quiet, yet access to all of the amenities within a 20 minute drive. Come to get away, or use it as a home base while exploring all that the Pembina Valley area has to offer. The Pembina Valley Provincial Park is 12 minutes away with picnic spots and ample hiking trails. Hy-Wire Zipline Adventures is only 1/2 an hours drive away.

Top guest favorite
Guesthouse in Winkler
4.98 out of 5 average rating, 62 reviews

Prairie Suite Guesthouse

This cozy 1-bedroom Airbnb offers a comfortable and private retreat, perfect for solo travelers or couples. Cleaning fees included We are located near the VBs entertainment centre, with plenty of restaurants nearby. ( KFC, Mr mikes, Burger King, Wendy’s, A&W , Chucks, Ralph’s German restaurant and buttercup. For fun : The meridian exhibition & golf course are about 4 minutes away, winners & landmark cinema are in the southland mall. Winkler has all you need! With minimal driving & traffic.

Top guest favorite
Barn in Stanley
5 out of 5 average rating, 11 reviews

Lucy’s Loft. Barn loft near Winkler.

Experience the charm of barn living in a brand new space designed for comfort, style, and relaxation. This newly built barn offers cozy but modern finishes boasting a clean, bright, and thoughtfully designed home away from home. Start your mornings with coffee and sunrise views, spend your days exploring or unwinding, and end your evenings in a quiet, welcoming space that is both unique and brand new. Perfect for couples, solo travelers, or anyone looking for a unique and relaxing getaway.

Superhost
A modest suite features a spacious bed with blue and white bedding. A kitchenette with a small sink and refrigerator is visible, along with a table and a folding chair. The floor is adorned with dark laminate, adding to the room's practical ambiance.
Apartment in Morden
4.8 out of 5 average rating, 25 reviews

Aspen Ridge Haven

We live in a quiet neighborhood on an acreage approximately three miles from the city. It is very wooded and pretty. The suite is a new build and a work in progress. It is a safe and comfortable space. It is not part of the main house, you do however walk through a wood work shop to enter the suite. The space includes a queen bed, table and chairs, Kitchenette includes fridge,stove, microwave and all the dishes etc. All linens are included, towels bedding etc. There is a three piece bath.

Top guest favorite
A glowing fire pit stands in the foreground, surrounded by a well-lit area. In the background, a spacious tent is illuminated softly, nestled amidst trees. The scene captures a serene nighttime atmosphere, with soft blue skies and hints of surrounding greenery.
Tent in Stanley
4.97 out of 5 average rating, 33 reviews

Hidden Valley Off Grid Glamping Tent

Get lost in this cozy rustic unique glamping trappers tent. You can often see and hear wild animals from the porch on the tent such as eagles, deers, and coyotes. The tent offers a fantastic view, situated on the valley edge. With natures music all around it’s a great place to unwind and disconnect. This off grid escape has out of this world star gazing, no light pollution. Excellent bird watching, novice or extreme hiking trails through the valley. A paradise for outdoor enthusiasts.

Guest favorite
A wooden pathway illuminated by string lights leads to the treehouse, reflecting warmly on the water. The structure's large window offers a glimpse of the interior, while trees line the background, creating a serene atmosphere at dusk.
Treehouse in Rosenort
4.93 out of 5 average rating, 272 reviews

Treehouse on the River

Reconnect with nature at this unforgettable escape just 30 minutes from Winnipeg. This cozy treehouse is a perfect getaway for rest, creativity and renewal. The single bedroom is surrounded by a wraparound deck with peaceful river views, offering a true sense of immersion in the outdoors. Finish your day and canoe along the river while watching wildlife or relax with a bon fire underneath a canopy of stars. Clear your mind in this serene setting. (bathroom on property 100 meters away)

Guest favorite
A wooden cabin is shown, featuring a steeply pitched roof and large windows. A small porch area is visible, with two chairs positioned on a lush green lawn. Surrounding trees create a natural setting, enhancing the secluded atmosphere.
Tiny home in Rosenort
4.89 out of 5 average rating, 55 reviews

Welcome to Bunkie Village!

Welcome to Bunk House #1, a sweet getaway only 35 minutes from Winnipeg. Located on a beautiful park-like property, with a bit of hobby farm feel. Be entertained by the chickens and pigs! Stroll the acreage, canoe in the pond, sit around the fire or indulge in apples/plums/raspberries when in season! There is a Bathroom Bunkie and an outdoor shower! Both the Bathroom Bunkie and Outdoor shower are available May - September Tranquil space to unplug, relax and reconnect with nature.

Top guest favorite
A spacious barn structure featuring a unique hip roof and large windows. The wooden exterior shows character and charm, surrounded by greenery and seasonal decor. A welcoming entrance is highlighted by a covered porch, offering a glimpse into the inviting atmosphere of the space.
Barn in Morden
4.99 out of 5 average rating, 115 reviews

Renovated Barn built in 1920s

Dive into the history of this unique and memorable place. This barn was built in 1925 and moved to its current location in 1986. The lovely oak staircase leads up to the 2nd and 3rd floors. The second floor features a full functioning kitchen, living area with leather furniture and TV, dining area with farmhouse table & chairs, a queen size bed, laundry room & 3 pce bath. Lovely cedar ceilings create ambiance and charm. The 3rd floor has 2 bedrooms with an ensuite in primary bedroom.

Popular amenities for Winkler vacation rentals

Quick stats about vacation rentals in Winkler

  • Total vacation rentals

    Explore 10 vacation rentals in Winkler

  • Nightly prices starting at

    Winkler vacation rentals start at G$4,192 GYD per night before taxes and fees

  • Verified guest reviews

    Over 340 verified reviews to help you choose

  • Wi-Fi availability

    10 of Winkler vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winkler rentals

  • 4.8 Average rating

    Winkler stays are highly rated by guests—averaging 4.8 out of 5!

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