Holiday rentals in Oakbank

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Top-rated holiday rentals in Oakbank

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

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Guest favourite
Home in Transcona
5 out of 5 average rating, 8 reviews

Velvet&Rose|Elegant Private 1BR Suite|Free Parking

Welcome to your cozy private retreat Enjoy a beautiful, clean, comfortable one-bedroom basement suite designed for a relaxing stay. Featuring a cozy bed, modern bathroom, and inviting living space, it’s perfect for unwinding after a long day. Located in a quiet, central area, you’re just minutes from shopping, dining, and city attractions. Includes free parking and fast Wi-Fi. Perfect for solo travelers or couples seeking comfort, privacy, and convenience. Book now for a peaceful memorable stay

Top guest favourite
Home in Transcona
4.94 out of 5 average rating, 35 reviews

Luxury 1 bedroom Basement suite (Private Entrance)

Luxury one bedroom basement suite in a quiet Winnipeg neighborhood. Perfect for short or long stays, business or leisure. • Living area with chairs, high speed Wi Fi, 65-inch smart TV with Netflix and Prime • Functional kitchenette with smart bin • Spacious bedroom with queen bed, closet, pillows, clean linens • Full bathroom with shower essentials, towels, and bidet • Onsite parking Close to Transcona Trails, Kildonan Mall, Safeway, Transcona Museum, Regent Casino, and Transcona Water Park.

Top guest favourite
Barn in Saint Germain South
4.99 out of 5 average rating, 80 reviews

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.

Top guest favourite
A cozy living and dining area is highlighted by warm wooden beams and exposed brick walls. A dark leather sofa is surrounded by artful decor and various plants. A dining table is set for a meal, complemented by stylish chairs and soft lighting from industrial fixtures.
Loft in Downtown Winnipeg
5 out of 5 average rating, 375 reviews

theLOFTonJAMES Authentic Industrial Warehouse Loft

Historic Architectural award winning Industrial Loft in the heart of the Winnipeg Exchange District, thoughtfully designed and curated. 📌 24 HR FREE PARKING INCLUDED 📌 Complimentary Museum Passes 📌 Early Check-In (subject to Availability) 📌​ Large fully equipped Chef's Kitchen 📌 Free WiFi 📌 2 Bedrooms with queen beds 📌 Smartlock 📌 Walking distance to Winnipeg's top 5 Tourist Destinations 📌 43" Smart TV with Netflix, Prime Video, Disney, Apple and more. 📌 In-suite​ Washer & Dryer ​

Top guest favourite
A modern living area features a black sectional sofa adorned with patterned cushions. A round coffee table sits in front, complemented by a decorative plant. The room is brightened by natural light from a window and showcases a clean, white panelled wall design.
Home in Transcona
4.97 out of 5 average rating, 155 reviews

Private 1BR Apt - Sep Entrance - Full Kitchen

Welcome! Enjoy our stylishly designed and exceptionally clean 1-bed self-contained basement suite with private entrance, full kitchen and Amenities. Just 16mins from downtown Winnipeg, the home is located in a serene neighbourhood with parks, nearby shopping, resturants and amenities. We are 5minutes drive from Kildonan Mall, Club Regent, grocery stores(Super Store, Walmart, Costco) and Concordia hospital. New to the City? The Forks is a great place to visit, we are just 13minutes away

Top guest favourite
Home in St. Boniface
4.99 out of 5 average rating, 221 reviews

Modern basement with all comforts in Bonavista

Looking for a getaway, private, quiet and tranquil place! 1 bedroom basement apartment with a kitchen side which comes with a fridge, microwave, kettle, coffee brewer, cutlery as well as basic serving utensils for your use. The room is equipped with an adjustable reading desk and chair, a treadmill for exercise and a queen bed that is warm and cozy for a perfect sleep. Fresh/clean towels are provided. It is located in a serene environment of the city with functional transit bus system.

Top guest favourite
A spacious outdoor deck is illuminated by string lights, featuring a comfortable seating area with a sectional sofa and a table. A hot tub with a soothing blue hue is positioned nearby, surrounded by trees, creating a serene and inviting atmosphere.
Treehouse in La Broquerie
4.99 out of 5 average rating, 158 reviews

Pine view Treehouse

Reconnect with nature at this unforgettable escape. Enjoy the 43 acres of privacy and 1.5 miles of walking trails. There are more amazing hiking and cross country ski trails in the nearby sandilands provincial forest. With hundreds of miles of ATV and snowmobile trails to explore, it will leave you with many great memories. This treehouse is great for couples and families to enjoy! The ground level deck is screened in to keep the bugs out while you relax in the 7 person hot tub.

Top guest favourite
A spacious bedroom is highlighted by a large bed with a dark headboard and soft bedding. Natural light filters through a window, framed by dark curtains. A small desk and lamp are positioned nearby, while recessed lighting enhances the overall ambiance.
Home in Winnipeg
4.96 out of 5 average rating, 413 reviews

Entire Suite in Crestview

Welcome to our amazing new suite nestled in a peaceful neighborhood in Crestview, just a stone's throw away from Winnipeg's finest dining establishments and shopping centers. Whether you're here for a relaxing getaway or a business trip, our location ensures convenience and tranquility. Situated a mere 15-minute drive from Winnipeg Airport and Polo Park, our suite is easily accessible. As part of a new duplex-style home, this unit offers complete privacy with its own separate entrance.

Top guest favourite
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, 287 reviews

Treehouse on the River

Reconnect with nature at this unforgettable escape just 30 minutes from Winnipeg. This cozy treehouse is a perfect getaway for rest, creativity and renewal. The single bedroom is surrounded by a wraparound deck with peaceful river views, offering a true sense of immersion in the outdoors. Finish your day and canoe along the river while watching wildlife or relax with a bon fire underneath a canopy of stars. Clear your mind in this serene setting. (bathroom on property 100 meters away)

Guest favourite
A child is seen leading a brown horse along a gravel path in the foreground. In the background, a house with large windows is visible, surrounded by green grass and a bit of landscaping. A red lawn tractor is parked nearby.
Guest house in Anola
4.82 out of 5 average rating, 72 reviews

Horse Farm Getaway

Relax with the whole family at this peaceful place to stay amongst our up and coming horse farm. Take a relaxing trail ride or just a getaway outside of the city; though we are located next to the train tracks, you are situated on 110 acre farm with groomed trails on site. This 4 seasons trailer has its own bathroom and kitchen; towels and dishes provided. Sorry no pets allowed as this is a fully functioning farm with various animals on site.

Guest favourite
The interior of the glamping dome features a queen-sized bed with a textured white comforter. A cozy seating area includes a wicker coffee table and two armchairs. Natural light filters through large windows, enhancing the space's connection with the surrounding forest.
Dome in Stead
4.93 out of 5 average rating, 140 reviews

Dome In The Woods

This off-grid 4 season glamping dome cabin is located on a beautiful 20 acre property at a 10 min drive from the shores of Lake Winnipeg and 5 mins away from Gull Lake. Enjoy walking on our forest trails, have a soak in our wood-fired hot tub or go explore the countless hiking trails nearby. Located just off a groomed snowmobile trail, this is a perfect home base for snowmobilers, ice fishermen and cross-country skiers in the winter time.

Guest favourite
A spacious living room features a large leather sectional sofa arranged around a central coffee table. A wall-mounted 55" smart TV displays the Netflix logo. Natural light streams in through large windows, illuminating the room's light hardwood floors and neutral-toned walls.
Home in St. Boniface
4.95 out of 5 average rating, 101 reviews

Riverfront 4BR Luxe w/ Hot Tub & Fire Pit

Riverfront retreat minutes from downtown! Unwind in the hot tub, gather by the fire pit, or stroll straight into Bois-des-Esprits forest. Inside: 4 spacious bedrooms, 2 baths, grand living room, game lounge with pool table, ping-pong, arcade, gym & smart TVs. Huge kitchen and dining for family feasts. Kayaks, riverside sunsets, walks on a frozen river and year-round adventure await—relax or explore, then book now to secure your dates!

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