Skip to content

Vacation rentals in Winkler

Find and book unique accommodations on Airbnb

When results are available, navigate with up and down arrow keys or explore by touch or swipe gestures.

Top-rated vacation rentals in Winkler

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite
Cabin in Roseisle, Canada
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.
Apr 17 – 24
$107 per night
4.99 out of 5 average rating, 146 reviews
Guest favorite
Home in Winkler, Canada
Bright Loft Space on Small Acreage in Winkler
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.
Aug 16 – 23
$102 per night
4.98 out of 5 average rating, 103 reviews
Guest favorite
Treehouse in Rosenort, Canada
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 skate along the river while watching wildlife or relax with a bon fire underneath a canopy of stars.
Dec 20 – 27
$63 per night
4.9 out of 5 average rating, 112 reviews

Popular amenities for Winkler vacation rentals

Other great vacation rentals in Winkler

Guest favorite
Barn in Reinfeld, Canada
The Roost in Reinfeld
Mar 30 – Apr 6
$56 per night
4.94 out of 5 average rating, 17 reviews
Guest favorite
Condo in Plum Coulee, Canada
🛏️ Cozy, Modern, Vibrant ☀️ Studio Suite
Mar 14 – 21
$33 per night
4.87 out of 5 average rating, 45 reviews
Guest favorite
Barn in Morden, Canada
Renovated Barn built in 1920s
Dec 27 – Jan 3
$110 per night
5.0 out of 5 average rating, 31 reviews
Guest favorite
Guesthouse in Stanley, Canada
Rural Retreat
May 3 – 10
$80 per night
5.0 out of 5 average rating, 15 reviews
Guest favorite
Home in Walhalla, North Dakota
Adorable 1 BR home close to Pembina Gorge
Dec 26 – Jan 2
$90 per night
4.92 out of 5 average rating, 39 reviews
Guest favorite
Guest suite in Friedensruh, Canada
2-bedroom suite with Sauna
Nov 4 – 11
$53 per night
5.0 out of 5 average rating, 6 reviews
Superhost
Tiny home in Stanley, Canada
Hidden Valley Off Grid remote tiny cabin
May 25 – Jun 1
$63 per night
5.0 out of 5 average rating, 3 reviews
Guest favorite
Home in Treherne, Canada
Cozy Getaway in Treherne
Dec 16 – 23
$67 per night
4.97 out of 5 average rating, 79 reviews
Guest favorite
Apartment in Cavalier, North Dakota
Roof Top Pines
Nov 3 – 10
$95 per night
4.89 out of 5 average rating, 38 reviews
Guest favorite
Home in Pembina, North Dakota
Unique, Charming, Comfortable 4 Bedroom Home
Jan 29 – Feb 5
$131 per night
4.84 out of 5 average rating, 38 reviews
Guest favorite
Apartment in Norfolk Treherne, Canada
Bison Hills
Jun 12 – 19
$103 per night
5.0 out of 5 average rating, 13 reviews
Guest favorite
Home in Cavalier, North Dakota
A completely revamped house in a central location.
May 28 – Jun 4
$225 per night
5.0 out of 5 average rating, 32 reviews

Destinations to explore

  1. Airbnb
  2. Canada
  3. Manitoba
  4. Stanley Region
  5. Winkler