Holiday rentals in De Winton

Guest house in Southeast Calgary

4.97 out of 5 average rating, 33 reviews

Chic & Cozy Brand-New Guesthouse (1 bedroom)

Welcome to our brand-new 1-bedroom suite! The bedroom features a queen bed with luxury mattress and memory foam pillows for a restful night’s sleep. Enjoy a spacious bathroom, in-unit laundry, and a fully equipped kitchen with all essentials. Relax in the cozy living room with a sofa, accent chair, and 65" smart TV with Netflix, Amazon Prime, Disney+, Paramont+, CraveTV and more. Designed for comfort and convenience, our suite is the ideal home away from home. Book your stay and unwind in style!

4.93 out of 5 average rating, 125 reviews

Guest suite in Foothills

Escape to the Country

Indulge in tranquility. A 6 minute drive south of town and yet you feel a long way from the hustle and bustle of life. Sitting on 4 private acres, entire suite is west facing with uninterrupted views of the valley below and onto the majestic Rocky Mountains. Enjoy the covered patio with fire pit and seating looking out onto the front lawn. This suite is perfect for a couple looking for a quiet retreat or a base to explore the surrounding area. Hot tub is available seasonally (September-May).

4.93 out of 5 average rating, 42 reviews

Guest suite in De Winton

Crocus Meadows suite

Relax at this beautiful and peaceful place. Enjoy friendly environment in 2 bedroom+den, 1 bathroom, full kitchen dining/living areas walkout guest suite (1500sqft). This beautiful getaway is located in Foothills county on a large acreage in private and quiet neighborhood. The guest suite is on the lower, walk-out level of the estate home. 15 min. from Calgary, Okotoks, Spruce Meadows, Sirroco Golf Course and The Calgary Polo Club. 40 min. from the Calgary International Airport. Very welcome.

4.98 out of 5 average rating, 142 reviews

♥You will love this 2BR Guest Suite in SE Calgary♥

This modern 2-bedroom apartment is a great option for business or pleasure. We are a few minutes drive from the South Health Campus, Real Canadian Superstore, and the World’s biggest YMCA. We provide FREE: ✓ Coffee & Tea ✓ Wifi ✓ Parking ✓ Quality toiletries and soaps ✓ 65" QLED Smart TV: Amazon Prime, Netflix & more ✓ Water & Drinks Other services include: ✓ Self-check-in ✓ Comfortable beds & pillows ✓ Warm duvets ✓ Washer & Dryer ✓ Iron ✓ Toaster ✓ Hairdryer ✓ Microwave oven

4.98 out of 5 average rating, 160 reviews

RUSTY RANCH A/C- TINY Charming Brand New Suite📍YYC

This unique place has a style all its own. Enjoy this BRAND NEW rustic-themed tiny suite for your perfect relaxed stay in Calgary’s southeast neighborhood, Seton. The area is conveniently located near the South Health Campus hospital and Fish Creek Park. Easy access to restaurants, banks, grocery & cineplex. Suite includes: - large HD TV with Telus channels, Netflix & Prime - Queen size bed - Microwave - Mini fridge - Standing shower - Central AC ACCESS IS ONLY TO THE GUEST SUITE

4.98 out of 5 average rating, 96 reviews

Guest suite in Okotoks

Crystal Green Retreat, 1 King & 1 Queen Suite

Come and stay in our luxury two bedroom, 1 bathroom lower level retreat. You will be instantly greeted with a cozy living area and stylish decor. Cozy up to a modern crystal fireplace and a comfortable large reclining leather sectional, while you enjoy watching a 80” smart theater TV. We offer a side bar with coffee station, microwave and fridge and freezer. There are 2 large bedrooms and walk-in closet with plenty of storage. The king size tempur pedic bed is absolutely heavenly.

5 out of 5 average rating, 17 reviews

Private guest suite in South Calgary

Kick back and relax in this calm, stylish space. This newly built guest suite has its own private entrance and everything you need to enjoy peaceful and undisturbed stay. Located in a family-oriented and serene community of Legacy, recently developed with ponds, walking paths, parks, kids playgrounds, picnic and recreation areas, our place is great for family vacation or a work trip. Community has its own shopping plaza with many stores, restaurants, bakeries, and gyms.

Superhost

Home in Southeast Calgary

5 out of 5 average rating, 3 reviews

Ultra-Luxe 9-Bed Escape | 2 Kitchens |AC |BBQ

Welcome to your stylish 5-bedroom, 3.5-bath retreat in Calgary’s sought-after Wolf Willow community—where comfort meets flexibility for families, friends, and larger groups. With 9 beds offering smart sleeping arrangements, central A/C, and a fully stocked kitchen, this home is designed for ease, relaxation, and connection. The spacious layout includes modern décor, multiple gathering spaces, and a private patio with a BBQ, ideal for outdoor dining or stargazing.

4.92 out of 5 average rating, 115 reviews

Tent in Priddis

Braided Creek Luxury Glamping

Indoor - Outdoor Living at its finest. Feel at home in the luxuriously appointed glamping tent just 12 minutes from South Calgary. Private, secluded tent located on a creek with an indoor fireplace, mini fridge, outdoor kitchen, hot shower, flushing toilet, power outlets. Plenty do to or nothing at all from exploring the nearby 166km of maintained trails in Bragg Creek, fishing the creek from your deck, to playing lawn games in your private 1 acre area.

4.89 out of 5 average rating, 125 reviews

SD Lodge

Welcome to our charming modern self-check-in lower unit! Just a short walk from a local grocery store for fresh produce and daily essentials. Craving a quick bite? Many fast-food options are nearby. Looking to unwind? A delightful wine and liquor store is just around the corner with an excellent selection for your evening. With its prime location and numerous nearby amenities, our place is the ideal choice for a comfortable, hassle-free stay.

Home in Southeast Calgary

4.96 out of 5 average rating, 271 reviews

SE Calgary Home with HOT TUB

This beautiful, luxurious home by Live@Jag’s is furnished with top-of-the-line stylish finishings, Hot Tub and quality BBQ (TRAEGER). “You don’t stay here, you live at Jag’s” Located in the quiet and gorgeous neighborhood of Auburn bay, this semi-detached property is perfect for family and friends to stopover. Located in Auburn Bay close to the new YMCA, South Health Campus (Hospital), Cineplex, + many restaurants and bars.

4.92 out of 5 average rating, 109 reviews

Cozy and new private basement suite

Get comfortable and enjoy plenty of extra room at this newly spacious place. Walk down the neighborhood to a beautiful lake. There are many restaurants near by and everything you can think of with easy access to major roads and highways. Only 20 minute drive to the main shopping centre, 30 minute to downtown, and 1.5 hours to Banff and the mountains. Surrounded by tons of fantastic trails.

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Other great holiday rentals in De Winton

Flat in Southeast Calgary

4.9 out of 5 average rating, 21 reviews

Elegant Cozy Private Apartment

JonathanRating, 5 stars1 week ago

Great spot if you are looking for a getaway. Very peaceful and relaxing environment. Clean suite and fantastic host. Would stay there again.

5 out of 5 average rating, 15 reviews

Guest house in Okotoks

Okotoks Oasis

ShelaneRating, 5 stars4 days ago

New place in a new development. In a year or so, this will be a beautiful spot with nearby parks and trails. Way better than staying at a hotel and more affordable. We enjoyed our stay very much. The family upstairs were very respectful and didn’t make much noise. Would stay here again if ever in Okotoks.

5 out of 5 average rating, 19 reviews

Guest house in Foothills

Cozy Country-Private, S.H.C. Hosp. Golf, Bow River

CandaceRating, 5 stars1 week ago

We loved our stay at Kandace's place for our anniversary weekend. The suite was cozy and well-appointed. We especially enjoyed the soaker tub and steam shower. There were clear instructions for how to use everything. Our only regret was not figuring out the TV. Kandace didn't see our messages for several hours but was willing to come and fix the issue once she did see it. We had decided to go to a movie instead. She even offered to reimburse us for the inconvenience, which was absolutely above and beyond! We didn't take her up on it because there were so many other extras provided which more than compensated for no TV! It was like a luxury camping excursion. We even enjoyed not having a full kitchen so we could totally ease up on our usual day-to-day. It was nice to go to the local restaurant near by or have snacks and charcuterie! We would happily stay there again if we're ever looking for an easy getaway in a quiet, peaceful spot with the convenience of city amenities close by.

4.88 out of 5 average rating, 26 reviews

Guest suite in De Winton

The Farmhouse @ Spruce Meadows/ Dewinton 2 bed

CharityRating, 5 stars2 months ago

We had a very comfortable stay and the host family was truly lovely. My first impression was that the home smelt and felt very clean. The space was nicer in person than the photos and furnished with thoughtful details including books, games, puzzles, some welcome snacks and coffee pods. We were made to feel at home and the hosts welcomed our puppy, as well. Being in the country was a bonus and we felt comfortable to walk the pup along the property. It is a gorgeous and convenient location close to Calgary and Okotoks. The beds were very comfortable and the hosts provided really lovely shampoo, conditioner and shower gel from Rocky Mountain Soap Co. 10/10 would recommend!

5 out of 5 average rating, 6 reviews

Cozy Luxe Suite | King Bed

MoniqueRating, 5 stars1 week ago

Super spacious basement accommodation! Everything felt clean and fresh. Really comfortable space to stay in. Thanks for having me.

5 out of 5 average rating, 27 reviews

1 BR walkout suite with kitchen, laundry + yard!

DeannaRating, 5 stars3 weeks ago

Loved our stay here! Very high end kitchen and appliances. Fabulous location for what we needed. Bedding was also high end. Home was spotless and we felt very comfy. Although it’s a basement suite, its basement walk in so it’s still bright and airy and no noise issues from above. Hosts were so helpful and accommodating. Would recommend this listing to anyone! We will be back

Superhost

Flat in Southeast Calgary

4.85 out of 5 average rating, 13 reviews

Designer-Inspired Stay 2BR, Parking, Workspace

RowenaRating, 5 stars1 week ago

We feel at home right away. We would recommend this place to our family and friends. So pristine clean and the house smells so good. We feel safe with all our belongings inside and a good plus for the covered garage. Will definitely book this place again when we come visit Calgary.