Vacation rentals in Winkler

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Top-rated vacation rentals in Winkler

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Guest favorite

A cozy studio suite is presented, featuring a queen bed with striped bedding and a wooden headboard. A small kitchen area equipped with a mini fridge and microwave is visible. A black dresser and a comfortable armchair with an ottoman complete the furnishings.

Condo in Plum Coulee

4.89 out of 5 average rating, 54 reviews

🛏️ Cozy, Modern, Vibrant ☀️ Studio Suite

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!

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, 166 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 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, 142 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 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

4.95 out of 5 average rating, 77 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.

Top guest favorite

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 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

4.88 out of 5 average rating, 50 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, 96 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.

Guest favorite

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, 18 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

Top 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, 235 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.

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, 143 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 favorite

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, 86 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.

Top guest favorite

A well-lit bedroom features a twin-size bed covered with a grey blanket against a light-colored wall. A small black bookshelf displays decor and books. A workspace with a chair and a simple table is positioned near the window, enhancing the functional layout.

Guest suite in Friedensruh

4.95 out of 5 average rating, 21 reviews

2-bedroom suite with Sauna

This is a comfortable 2 bedroom suite including a kitchen, washer dryer and a Sauna. Private entrance and parking. Bedroom 1 has a queen size bed. Bedroom 2 has a twin size bed. More than 3 people can be accommodated. Please inquire. The suite is attached to a larger house in the village of Friedensruh about 10 minutes southeast of Winkler.