Vacation rentals in Winkler

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Top-rated vacation rentals in Winkler

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Guest favorite

Condo in Plum Coulee

4.88 out of 5 average rating, 49 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!

Superhost

Cabin in Roseisle

4.99 out of 5 average rating, 156 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

Home in Winkler

4.98 out of 5 average rating, 123 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.

Guest favorite

Home in Cavalier

5 out of 5 average rating, 39 reviews

A completely revamped house in a central location.

Completely new updates throughout. Room for kids to play. Located within walking distance of the pool, city park and main street. A short drive or bike to Icelandic State Park and approx. 30-40 mins to Frost Fire Ski Resort. Enjoy your family reunion, of family vacation. Upstairs: King bedroom, Queen bedroom, shower/bathroom Main Level: Kitchen, dining, living room, TV room, laundry, bathroom with walk in shower. Lower Level: Bunk room (2 bunk beds and two twin beds) with bathroom/shower.

Guest favorite

Home in Walhalla

4.93 out of 5 average rating, 59 reviews

The Sherlock Home close to Pembina Gorge

Your home away from home! The Sherlock Home is happy to offer a fully furnished vacation rental in the Valley of the Gods - Walhalla! 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. We have a deck, firepit & off-street parking with room for trailers in the spring, summer and fall. Count on anything you find in a regular hotel room + household basics + a few home-like bonuses!

Guest favorite

Barn in Morden

4.98 out of 5 average rating, 64 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

Tiny home in Langdon

5 out of 5 average rating, 28 reviews

Up North Cozy Cabin near Pembina Gorge

Explore a 9-acre property 9 miles west of the Pembina Gorge. View Northern Lights and relax under the stars. Plenty of parking for trailers/ATVs. This property positions you to be in nature's northern playground: 13 miles from Langdon, 10 miles from Frost Fire Park, and 17 miles from 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."

Guest favorite

Treehouse in Rosenort

4.94 out of 5 average rating, 172 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. This 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 favorite

Home in Pembina

4.86 out of 5 average rating, 65 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.

Guest favorite

Barn in Neubergthal

4.99 out of 5 average rating, 124 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.

Guest favorite

Guesthouse in Stanley

5 out of 5 average rating, 38 reviews

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 and strawberry picking on cool evenings when in season. well designed cottage to meet most daily needs.

Guest favorite

Guesthouse in Winkler

4.98 out of 5 average rating, 60 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.