Holiday houses in Winkler

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Top-rated holiday rentals in Winkler

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Apartment in Winkler
5 out of 5 average rating, 3 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 ✔ Double-Size Bed ✔ Smart TV ✔ Modern Lighting & Clean Design ✔ Convenient Location

Top Guest favourite
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, 169 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.

Top Guest favourite
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, 149 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 favourite
The exterior of a vintage home presents a blend of muted green and grey siding, with a welcoming deck at the entrance. A patio area is shown, featuring seating and a grill. A sprawling yard is visible, framed by mature oak trees.
Home in Walhalla
4.94 out of 5 average rating, 81 reviews

The Sherlock Home close to Pembina Gorge

Your home away from home! The Sherlock Home is your a fully furnished vacation rental! With one bedroom (king size bed), one bath + queen size air bed (24" high), we can accommodate 4 guests. There's plenty of space for outdoor entertaining, including a deck, firepit & off-street parking with room for trailers. The perfect place to soak in the view of the hills and the Pembina Gorge & outdoor activities: hunting, ATVing, kayaking, skiing, golfing, mountain biking, snowmobiling, and hiking.

Guest favourite
A cozy suite features a spacious bed with neutral bedding. A comfortable armchair is positioned next to a large window, which allows natural light to fill the room. Air conditioning is provided, and a white small table adds a functional touch.
Condo in Plum Coulee
4.91 out of 5 average rating, 11 reviews

Copper Studio - Long Term Stays!

Welcome to Plum Coulee, this cozy suite is walking distance to the beach, restaurant, grocery store, laundry mat, local park & museum. Enjoy the laid back, quiet and relaxed small town living. This location is perfect for guests working out of town and is centrally located from numerous job communities with a short drive: Location - Mins Winkler - 12 Morden - 18 Altona - 19 Gretna - 24 Explore the Pembina Valley, hiking trails, zip lines, arts & culture, parks, beaches, golf courses & more!

Top Guest favourite
A cozy living area is presented with a gray sofa adorned with red accents and a patterned area rug. A comfortable armchair complements the space. Large windows provide natural light and offer a view of outdoor seating on a wooden deck.
Tiny home in Langdon
5 out of 5 average rating, 47 reviews

Up North Cozy Cabin near Pembina Gorge

Enjoy a boutique nature retreat! This 9-acre property is 9 miles west of the Pembina Gorge. View Northern Lights and relax under the stars. Plenty of trailers/ATV parking. Enjoy the great outdoors: 4 miles to Mount Carmel Dam, 10 miles to Frost Fire Park, 13 miles to Langdon, and 17 miles to Walhalla. Sleeps 6: two bedrooms with queen size beds and a sofa sleeper with queen size mattress On a sceptic system with well water. Located on same property as "Up North RV near Pembina Gorge."

Top Guest favourite
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, 106 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.

Top Guest favourite
A spacious living area features a high wooden ceiling with pendant lights illuminating the room. A sectional sofa is placed adjacent to a wooden coffee table, and an artwork decorates the wall. A kitchen area with modern appliances is visible in the background.
Home in Rhineland
5 out of 5 average rating, 20 reviews

Prairie Wind Ranch House

Prairie Wind Ranch House is located on the outskirts of Altona Manitoba, in the small village of Gnadenfeld. This 3 bedroom, 2 bath ranch style home on a 2 acre yard has plenty of space to entertain family and friends, romantic weekend getaways. Perfect for baseball weekends, wedding groups and stag or stagette parties. And all within distance to shops, groceries, restaurants and local attractions. Altona is 2km, Winkler is 42km, Morden is 56km, The Gables Wedding Barn is 12km

Guest favourite
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, 254 reviews

Treehouse on the River

Reconnect with nature at this unforgettable escape. This cozy treehouse is perfect for a getaway just 30 minutes from Winnipeg. The one level bedroom is surrounded by a wrap around deck overlooking the river. (bathroom on property 100 meters away) This space is the perfect place to rest, create and rejuvenate while maintaining a space to clear your mind. Finish your day and canoe along the river while watching wildlife or relax with a bon fire underneath a canopy of stars.

Guest favourite
The entrance of a two-story home is framed by vibrant autumn foliage. A path leads to wooden steps and a welcoming front door. Surrounding greenery is visible, with fallen leaves covering the ground, creating a peaceful and inviting atmosphere.
Home in Pembina
4.85 out of 5 average rating, 85 reviews

Unique, Charming, Comfortable 4 Bedroom Home

Bring the whole family to this unique home with lots of room for friendship, fun and family engagement. Spacious kitchen and bedrooms, comfortable living/family room, classic dining room. Quiet, small town America, just two miles from Manitoba and Canada. Convenient stopping place for Canadian tourists heading back home. High-speed internet, ample room for business activities. Beautiful facility to just get away and relax. Four bedrooms, sleeping room for 10.

Top Guest favourite
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, 147 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 3 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.

Top Guest favourite
An open concept living area is seen, featuring a cozy sofa and dining table set for four. A well-equipped kitchen is visible with white cabinetry and modern appliances. Natural light enters through a glass door leading outside.
Guesthouse in Winkler
4.99 out of 5 average rating, 92 reviews

Friesen’s Place

Friesen’s Place is a home away from home, located in a quiet residential area of Winkler. Enjoy your stay in the privacy of your very own house nestled in the corner of the backyard. There is a barbecue and patio set in your own private outdoor space within a fenced yard. Friesen’s Place is conveniently located within a 5-minute drive downtown, parks and business centre.

Popular amenities for Winkler holiday rentals

Quick stats about holiday rentals in Winkler

  • Total holiday rentals

    Explore 10 holiday rentals in Winkler

  • Nightly prices starting at

    Winkler holiday rentals start at $35 NZD per night before taxes and fees

  • Verified guest reviews

    Over 290 verified reviews to help you choose

  • Wi-Fi availability

    10 of Winkler holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Winkler rentals

  • 4.9 Average rating

    Winkler stays are highly rated by guests—averaging 4.9 out of 5!

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