Holiday rentals in Montgomery

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Top-rated holiday rentals in Montgomery

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

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Top guest favourite
A bright open living area features a dark sectional couch paired with a light ottoman. A kitchen island with modern countertops is equipped with bar stools. Large windows allow natural light to fill the space, while decorative accents enhance the welcoming atmosphere.
Guest house in Bowness
4.94 out of 5 average rating, 140 reviews

NW Lane Home/Winsport view/private/no clean fee

Enjoy winter and kick back and relax in this calm, stylish space. Enjoy the privacy of a fully separate home with view of Canada Olympic Park (Winsport) and evening sunsets. Luxury features including central air conditioning, quartz counters, hardwood floors and rejuvenating air tub. Located a short walk to the Bow River and quick access to the Trans-Canada Highway (Hwy 1) for your mountain adventures! Includes private single heated garage and off street parking for your short or long term stay.

Guest favourite
A cozy living area features a large sectional sofa with decorative throw pillows. A glass coffee table is positioned atop a textured area rug. A smart TV is located on a white media console, with dining and kitchen areas visible in the background.
Home in Montgomery
4.98 out of 5 average rating, 55 reviews

Central Oasis | Close to Hospital | River |UofC

Stay in the heart of the sought-after Montgomery community! Perfect for work or relaxation: Prime Location: -Easy access to U of C, Market Mall, Parks, Schools, Public Transit -Close to Foothills & Children's Hospitals, SAIT, River Living: -2 cozy bedrooms -Fully stocked kitchen + Coffee -Washer & Dryer In Unit Amenities: -Workspace: 24" monitor, keyboard, mouse, printer -58" Smart TV -High-speed internet Parking: -Parking for 2 vehicles + free street parking Relax and enjoy a seamless stay!

Top guest favourite
Home in Calgary
5 out of 5 average rating, 10 reviews

Minutes to Children's Hospital/UofC—Luxury NW Home

💎 Montgomery Carriage House! Luxury 2-BR detached garage suite. No shared walls or neighbors! Minutes to Foothills & Children’s Hospitals, WinSport/COP, and Banff access. 🛌 King Bed + Blackout Blinds 🚿 Heated Bathroom Floors ❄️ Central A/C 🍳 Full Modern Kitchen + Coffee 💻 High-Speed Wi-Fi & Smart TVs 🧺 Private In-suite Laundry 🌲 Steps to Bow River Trails & Parks 🎓 Near UofC Oval & University District ✨ Professional & Private. Your upscale base for medical stays or mountain adventures!

Top guest favourite
A spacious bed with a clean, white duvet is centered in the room, flanked by two bedside tables with modern lamps. A wall art piece depicting a scenic landscape is visible above the bed. Soft, light-colored carpet covers the floor, enhancing the room's aesthetic.
Guest suite in Montgomery
4.96 out of 5 average rating, 198 reviews

Modern & Spacious 1B - Close to UofC & Hospitals

Beautiful, bright, modern, legal/registered basement suite with a private entrance in a Montgomery infill. Minutes from Foothills and Children's Hospitals, University of Calgary, Market Mall, Shouldice and Edworthy Parks, and river pathways and dog parks. 10-15 minute drive to downtown Calgary, and a quick getaway out west for a Rocky Mountain adventure. Contemporary open floor plan living room and kitchen. In-suite stackable washer and dryer. Pets welcomed for an extra fee ($25 Canadian)

Superhost
A charming house with a welcoming entrance features a light-colored facade and a decorative front door. Colorful flower baskets hang by the front steps, and lush greenery lines the walkway, offering a serene presence. The surrounding area includes well-maintained shrubbery and trees, creating a peaceful atmosphere.
Guest suite in Montgomery
4.78 out of 5 average rating, 238 reviews

Chateau Near the Bow in Montgomery

Would you like to stay in one of the Calgary’s trendiest inner-city areas close to EVERYTHING? Are you an active outdoor enthusiast or prefer the quite solitude of an established community? Then, welcome to the Chateau Near the Bow - a space you can call your home! Enjoy a spacious 2-bd basement suite with private entrance, full jetted bathroom, high ceilings, large windows and a fully equipped kitchen combined with outdoor barbecue and fire pit dining facilities. Business Licence 234292

Top guest favourite
A light-filled living area is presented, featuring a spacious sectional sofa adorned with various cushions. A low coffee table is positioned centrally on an area rug, and a wall-mounted television is visible across from the seating. Large windows provide natural light and views of the outdoors.
Guest house in Southwest Calgary
4.98 out of 5 average rating, 227 reviews

Luxury private carriage house with character!

Enjoy a stylish experience in this bright and open carriage house located in a very desirable part of the city. Close to restaurants, shopping, downtown, the Saddledome, Mount Royal University, and much more! The architect-designed suite is one of a kind and full of character and natural light. Relax with a coffee or a glass of wine on the covered private balcony or take a short walk to Marda Loop, one of Calgary's premier dining destinations! Max occupancy is 2 adults & 1 child under 12.

Top guest favourite
The exterior of the residence features a two-story design with a stone façade and a spacious garage. Large windows illuminate the front, while a driveway leads from the street. Greenery is present alongside the home, contributing to the overall inviting appearance.
Guest suite in Aspenwoods
4.97 out of 5 average rating, 402 reviews

NO CLEAN FEE*Modern Basement with own entrance

Relax with the whole family at this peaceful place to stay. Our place has a door separating upstairs and basement and a private entrance and in an affluent area of Calgary. It's quiet, safe and boasts panoramic views of Aspen Woods. Only a 5 minute walk to Aspen Landing and Blush Lane Organic Market where you will find a variety of restaurants, pharmacies, coffee shops, grocery, liquor stores & more. 5min drive to C-train and 15 min drive to downtown. A quick drive to Banff and airport.

Top guest favourite
A retro soda shop-style kitchen and living area is highlighted by a checkered black-and-white floor. A bright red Coca-Cola fridge stands prominently, while a counter with three stools invites seating. Artistic soda shop signage adorns the walls, enhancing the nostalgic atmosphere.
Flat in Southwest Calgary
4.87 out of 5 average rating, 551 reviews

1950's Soda Shop suite

No Cleaning Fee ! Basement Suite 5 Minutes from Banff highway on western edge of Calgary !!!!! City of Calgary license number BL236879 Spend some fun time in our 1950's Soda Shop suite !! One bedroom with queen bed, ............ also have an inflatable queen size air bed for extra guests as well as a couple of roll-a-way cots available for kids. 1000 square feet ground level, private entrance beautiful backyard oasis with patio, firepit, waterfall & pond water feature

Top guest favourite
Home in Calgary
5 out of 5 average rating, 15 reviews

The Nordic Glow - 3-BR, Wifi, Yard, +Style

Step into this stunning upper-level home that blends modern elegance with cozy comfort. Designed with style and function in mind, this space offers the perfect retreat for families, professionals, or groups looking for a memorable stay. This home isn’t just a place to stay—it’s a design-forward experience. From the warm wood accents and custom tilework to the thoughtfully chosen furnishings and spa-inspired ensuite, every detail was created for comfort and sophistication.

Guest favourite
Home in Montgomery
5 out of 5 average rating, 9 reviews

Private Walkout Basement

This private walkout basement suite is located in a quiet neighborhood with many parks and close to the Bow River. The unit has everything you need for a short stay including a fully equipped kitchen, a separate laundry room and free street parking. Walkable distance to Market Mall, University of Calgary and Alberta Children’s Hospital and less than 10 min drive to Foothills Medical Centre. It has easy access to downtown and Banff and bus stops are minutes away.

Top guest favourite
A spacious living area features a modern gray sectional sofa complemented by a round coffee table. High ceilings enhance the open feel, while light wood flooring offers warmth. A minimalist dining area with four black bar stools is positioned at a sleek white kitchen island.
Guest suite in Montgomery
4.98 out of 5 average rating, 48 reviews

UofC | Market Mall | Hospitals | Downtown | Banff

Private basement suite with a separate entrance. Free street parking. Minutes from Foothills and Children's Hospitals, University of Calgary, Market Mall, parks and river pathways. Centrally located with easy access to downtown and Banff. Bus stops within a 2-min walk. The kitchenette is stocked with new amenities including, mini fridge, microwave, Nespresso machine, toaster and more. The 10-foot ceiling will leave you feeling you’re on the main floor!

Top guest favourite
Guest suite in Montgomery
5 out of 5 average rating, 9 reviews

New 2BR Near DT, Hospitals, U of C & Shopping

Welcome to our 2-bedroom legal suite in the vibrant Montgomery area! Just 10 minutes to downtown and minutes from Foothills Hospital, Children’s Hospital, U of C, and the Bow River. Also a few minute drive to my favourite mall, Market Mall. Enjoy a full kitchen, large windows, private entrance, and free parking. Perfect for medical visits, work trips, or mountain getaways. Clean, comfortable, and thoughtfully stocked for a great stay.

Popular amenities for Montgomery holiday rentals

Quick stats about holiday rentals in Montgomery

  • Total holiday rentals

    Explore 70 holiday rentals in Montgomery

  • Nightly prices starting at

    Montgomery holiday rentals start at $38 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,580 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    70 of Montgomery holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Montgomery rentals

  • 4.8 Average rating

    Montgomery stays are highly rated by guests – averaging 4.8 out of 5!

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