Vacation rentals in Anola

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Top-rated vacation rentals in Anola

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

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Top guest favorite

The living area features a sleek black leather sofa accompanied by two modern chairs. A glass coffee table sits on a geometric patterned rug, while a metallic floor lamp stands in the corner. The walls are painted in soft gray, complementing the wall art above the sofa.

Home in Winnipeg

Bright & Spacious 3 Bdrm Home, Close to downtown

Bright & spacious, 3 bdrm, 6 guest home within 10 mins drive to downtown, walking distance to city bus, restaurants or a scenic walk along the river. You will feel right at home in this modern/contemporary 2-storey newer home which has a full eat-in kitchen with fridge, stove, dishwasher and microwave, 1 1/2 baths, comfy beds, Smart TV, Wifi, washer/dryer in a full basement, central A/C, fenced in front yard, parking in back yard or on front street, and easy self check-in. Kids & pets welcome.

FamilyValueParking

4.95 out of 5 average rating, 607 reviews

Top guest favorite

A spacious games room features a bright blue pool table at its center, surrounded by comfortable seating areas. Large windows provide ample natural light, and a wood stove adds warmth to the space. The walls are adorned with various decorative elements.

Cabin in Marchand

Private house w/ 7 rms & close to amenities

Beautiful Whole house with 7 bedroom, 3 bathroom with 2 half bathrooms, fully stocked kitchen, games room with pool table, large fenced backyard with big fire pit area, wifi, smart tv's in bedrooms and games room, coin-op laundry, large circular driveway with lots of parking for large trailers. Extensive trail system just 5 minutes up the road. Gas station directly across the street, vender/bar right next door! Min. 2 bedrooms for 4 guests. Additional fee for additional guests and cleaning fee.

FamilyLocationBackyard

4.97 out of 5 average rating, 129 reviews

Top guest favorite

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

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

LocationFamilyCheckout

5.0 out of 5 average rating, 385 reviews

Top guest favorite

A vibrant red cabin is set against a clear blue sky, surrounded by greenery and natural landscape. A simple wooden table is positioned in the foreground, providing a space for outdoor dining or relaxation.

Tiny home in Richer

Little Western Cabin

Need a place to relax with your significant other, or maybe just get away on your own? Book your getaway to this cozy little Western Cabin. Located in Wild Oaks Campground this cabin is the perfect place to connect with nature and each other. Take a dip in the pond during the summer months, or enjoy the hot tub and pool. Bring your snow shoes in the winter and enjoy a hike outside on one of our many trails, or get cozy by the campfire. (Hot tub/pool are not open starting September 8th-May 1).

ValueLocationCleanliness

4.89 out of 5 average rating, 305 reviews

Guest favorite

Home in West St. Paul

COZY Relaxing Luxury House in Countryside Living

Bring the whole family to this great place with lots of room for fun. Toys and books for kids Gym equipment for exercise Big Patio deck for enjoy in THE SPACE Big kitchen and big living room Enjoy exclusive access to this luxury house with lots OF amenities are all yours with driveway parking up to 10 vehicles SLEEPING PRIMARY SUITE, KING BED WITH NIGHTSTANDS AND WALK-IN CLOSET A BIG WASHROOM WITH DOUBLE SINK, SHOWER AND JACUZZI to enjoy ALL SIX ROOMS HAVE QUEEN BEDS AND WALK-IN CLOSET

LocationFamilyOutdoor spaces

5.0 out of 5 average rating, 18 reviews

Top guest favorite

Cabin in Grand Marais

Black Aspen Green Dog-Friendly Cabin - Near Beach

Black Aspen Green: Have fun with the whole family at our modern cottage near the beach. Walking distance to the beach, our dog friendly space boasts comforts for everyone. This modern cottage was designed for a large family or for two families to share. 3 bedroom, 2 bath including a bunk room for the kids and a mudroom with built in kennels and a dog bath. The backyard has a large ground level deck with two BBQs, seating and dining spaces as well as a fire pit area with plenty of seating.

FamilyValueTV

4.99 out of 5 average rating, 138 reviews

Top guest favorite

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

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.

FamilyValueCheckout

4.99 out of 5 average rating, 177 reviews

Top guest favorite

A spacious bed is dressed in white linens, complemented by a neutral throw at the foot. Nightstands with plants adorn either side of the bed, and soft wall sconces provide ambient lighting. A serene artwork piece is mounted above the headboard.

Home in St. Boniface

2BR separate unit/ kitchen

Peaceful, centrally located in St. Boniface. Host bilingual English/French. Very near hospitals (St.Boniface and HSC), shopping, groceries, restaurants and 5 min drive to The Forks. Close access to Trans Canada Hwy. Large 2BR unit with King and queen bed. Separate entrance with self check-in. Baby play pen on-site and laundry available upon request. Host resides upstairs. Kitchen includes basics (salt, pepper, oil, tea). Nespresso (pods provided). Breakfast items provided. TV (CRAVE)

LocationFamilyTV

5.0 out of 5 average rating, 211 reviews

Top guest favorite

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

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)

LocationValueAmenities

4.93 out of 5 average rating, 309 reviews

Guest favorite

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.

Guesthouse in Anola

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.

LocationValueComfort

4.83 out of 5 average rating, 77 reviews

Top guest favorite

A modern kitchen showcases sleek cabinetry with light wood and dark grey finishes. An island with a marble countertop features two brown leather bar stools. Stainless steel appliances and a well-organized countertop are evident, while ambient lighting highlights the open layout connecting to a cozy living area.

Home in Winnipeg

Brand New Home! Osborne, 3 Bed, 2.5 bath

Welcome to Your Osborne Sanctuary! Perfectly located near Winnipeg’s top attractions. From cozy coffee shops, and unique restaurants, to the iconic Park Theatre, this vibrant neighborhood offers a hub of culture and culinary delights. Explore scenic walking trails, tree-lined streets, and Park Alleys Bowling. Just minutes from downtown, enjoy easy access to BDI Ice Cream, community markets, and serene parks. Your Osborne retreat awaits!

LocationFamilyCleanliness

4.98 out of 5 average rating, 167 reviews

Top guest favorite

Home in St. Boniface

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!

ValueFamilyCheckout

4.95 out of 5 average rating, 128 reviews