
Holiday houses in Winkler
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Top-rated holiday rentals in Winkler
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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.

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.

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.

River Creek Retreat
Experience the quiet of our 900-sq ft timber frame straw-bale suite. Relax in the eco-friendly hot tub. The private, main floor suite is surrounded by gardens and trees. Situated on an acreage 11 kms south of Winnipeg, only a 30 minute drive from downtown (10 min longer now, due to road closure). A lovely close-to-the-city location that feels remote and relaxing. In winter, experience the luxury of radiant floor heating. In summer, marvel at how the space remains cool without air conditioning.

Cozy, Relaxing - Studio Suite - 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!

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.

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

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.

Peaceful Retreat in the Bush
Welcome to a peaceful oasis, tucked away in the bush, away from the business of life. This newly built one-of-a-kind house is a gorgeous retreat, complete with 60 acres of bush to explore, a top of the line hot tub, and a cozy wood burning fireplace, and plenty of friendly cats to keep you company. Just a few minutes away you can enjoy a round of golf at our local course in the summer, and the snowmobile trails are just around the corner in the winter.

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.

Rural Retreat
Take it easy at this unique and tranquil getaway. we are located 1 and 3/4 miles from the Boundary trials health center, only 2 miles from town yet its a country hide away. this 2 bedroom guest house is located on 2 acres of recreation including a rural beach. Surround by trees. Raspberry picking on cool evenings when in season. well designed cottage to meet most daily needs.

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.
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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 $31 AUD per night before taxes and fees

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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!