
Holiday houses in Winkler
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Winkler
Guests agree: these stays are highly rated for location, cleanliness and more.

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

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.

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!

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."

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.

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.

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.

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
Other great holiday rentals in Winkler

Serenity Bed and Breakfast

Cozy Eco-Cabin in the Valley

Bella's Castle | Penthouse Suite

Bell Aura ~ Gable Room

cozy basement suite

House of Comfort 2BR Basement

Town & Country

Featherstone Farm Cabin
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!




