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Apartment holiday rentals in Winchester

Find and book unique apartments on Airbnb

Top-rated apartment rentals in Winchester

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

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Guest favourite
A modernized rustic kitchen features wooden wall accents and a stylish bar area with two chairs. Sleek appliances, including a refrigerator and stove, are visible. Natural light flows through a nearby window, highlighting the clean lines and inviting setup.
Flat in Montebello
4.92 out of 5 average rating, 153 reviews

The Zen suite

Rustic-Chic Retreat in Montebello Stay in the heart of Montebello, steps from the Fromagerie & marina, This cozy, zen-inspired retreat is perfect for couples or friends seeking comfort and adventure 🛌 Queen bed for 2 guests 🛁 Stylish, unique bathroom 🎥 75'' TV, Netflix, comfy sofa, and Wi-Fi 🚗 5 mins to Parc Omega Nearby Activities: Explore Château Montebello and its amenities Local shops, cafés, and restaurants Hiking ,biking ,golfing ,Parc Omega Papineau-Labelle Reserve and more

Top guest favourite
A balcony extends from the loft, featuring wooden flooring and a shade awning above. Two black chairs are positioned along the railing, offering views of the surrounding farmland under a clear blue sky.
Flat in Greely
4.97 out of 5 average rating, 217 reviews

Walk 2 OLRT & Hard Rock, mins to airport & EY Ctr

A one-of-a-kind stay; this cozy loft nestled inside a converted airport hangar has rustic charm, curved ceilings, & wide-open views. It offers the perfect blend of character & convenience. Relax on the balcony & watch stunning sunsets, explore the open space, or hit the nearby trails for a walk or bike ride. Enjoy Starlink Wi-Fi, AC, a dedicated workspace, and a stocked pantry. Just 7 minutes from the airport & EY Centre, 2 mins. from the Hard Rock & Casino, golf course, & 20 mins. to downtown.

Top guest favourite
A grassy area is highlighted by a large tree featuring a playset with a slide. In the background, tranquil water reflects the sky, while a shed stands nearby. The scene is framed by scattered clouds and greenery.
Flat in Edwardsburgh/Cardinal
4.89 out of 5 average rating, 174 reviews

1000 Islands waterfront accommodation

Amazing hot tub & patio both with awesome river view!-DSL hi-speed wifi-17 min Brockville-Gorgeous 1000 sq ft walk-out St. Lawrence River secluded waterfront accommodation! Ambient in-floor heating to compliment beautiful gas fireplace! Grand rm features custom kitchen with hand-crafted pine cabinetry & a wall of 4 very tall south-facing windows/patio doors-Hi-end 4-piece bath-Mstr quarters offer king-sized bed/his & hers closet space-2nd bdrm has queen murphy bed-Enjoy kayaks/fish from dock!

Guest favourite
An open living area features a wooden dining table with white chairs, accompanied by potted plants. A sleek white sofa sits nearby, with a cozy throw draped over it. Natural light pours in through multiple windows, enhancing the spacious layout.
Flat in Chelsea
4.89 out of 5 average rating, 333 reviews

Lovely modern 2 bedroom open space apartment

Beautiful well appointed 2 bedroom modern open space apartment with fully furnished kitchen in charming Old Chelsea. Within walking distance from the Gatineau Park, center village's bistros, boutiques, Nordik Spa and farmer's markets. Outdoor enthusiast can start their hike or hit the cross-country/snowshoe trails across the street from the airbnb. For the more adventurous, Camp Fortunes ski resort's cross-country mountain bike trails, aerial park zip lines and slops are only a 5 min drive.

Guest favourite
A cozy living area features a comfortable sectional sofa adorned with patterned cushions. A TV sits on a low stand, and a projector is mounted on the ceiling. A spacious bed is partially visible, alongside decorative elements like a wall clock and small shelves.
Flat in Gloucester
4.97 out of 5 average rating, 147 reviews

Lynn's Cozy Nest

Welcome to Lynn’s Home Nest! Just a 10-minute drive from the airport, our cozy 2 bedroom guest suite is perfect for families and remote workers alike. Enjoy high-speed WiFi, dedicated workspaces, and lots of room to relax. The kids will love the family area, while adults appreciate the fully equipped kitchenette and living spaces. Unwind on the private patio, explore nearby parks, or check out local dining. Ideal for work, family time, or both - Lynn’s place has it all for a perfect stay!

Guest favourite
A two-story house is illuminated softly in the evening light, highlighting its brick facade. A well-maintained lawn with potted flowers frames the entrance. A vehicle is parked in the driveway, with large windows allowing a view of the home's interior.
Flat in Manotick
4.92 out of 5 average rating, 103 reviews

Apartment with Big Lounge

Book with confidence! Experienced host with 80+ FIVE-STAR ⭐⭐⭐⭐⭐ reviews on our property. Welcome to our stylish, large and independent 1-bedroom apartment with a spacious living area for work or relaxation. The layout features a kitchenette with all essentials and a dedicated office desk with high-speed internet for remote work. Located in a quiet and beautiful neighborhood, ideal for couples or business stays. Enjoy convenience near local attractions, restaurants, and sightseeing!

Top guest favourite
A window offers a view of the Mississippi River framed by sheer curtains. Lush greenery and outdoor seating are visible in the foreground, with trees lining the riverbank and a small deck accessible from the water's edge.
Flat in Mississippi Mills
4.98 out of 5 average rating, 166 reviews

Heron's Nest on the Mississippi -Couple's Getaway

Absolutely unique space. Newly renovated, with private entrance, one bedroom apartment on the Mississippi River. Beautiful views with a patio & terrace overlooking the river. Minutes walking to shops, restaurants, galleries, bike & walking trails, birdwatching, river boat launch, fishing & downtown core. Full kitchen, WIFI & TV. A great couple's getaway. Two day booking minimum, although special requests may be accepted & discounts given for weekly and monthly rentals.

Top guest favourite
A collection of vintage items is displayed against a bright yellow wall. Notable elements include a retro Pepsi-Cola sign, a vibrant red popcorn container, and various decorative mugs. A small toy car, a Polaroid-style camera, and an assortment of playful signs add character to the arrangement.
Flat in Prescott
4.96 out of 5 average rating, 308 reviews

2 Bedroom Vintage Suite (mid-term available)

The 2 bedroom apartment is located on the 2nd floor and can accommodate 4 guests. The suite is in the Mechanic Block and dates back to 1874. The apartment was restored while keeping the historical integrity in check. With vintage sink, clawfoot tub and 7' interior walls (not reaching ceiling as shown on photos) There is private parking and separate entrance. You get the entire apartment. The main level of this historical commercial building is operated by the building owner.

Top guest favourite
Flat in Gatineau
4.93 out of 5 average rating, 120 reviews

The loop - CITQ 321091

NON-SMOKING LEVEL 2 car charging station ($ to be discussed). Private apartment and private entrance. On-site parking. Full kitchen, bathroom with shower. Queen bed with quality feather duvet. Bed with anti-mite cover. Laundry room in the house Pets allowed (with approval). Netflix, Disney and Prime included. High-speed internet. Outdoor cameras, smoke and carbon monoxide detector, fire extinguisher, unique code lock, various emergency exits, outdoor lighting, etc.

Top guest favourite
Flat in Westboro
4.94 out of 5 average rating, 152 reviews

Sunny Westboro Retreat | Walk to Everything

Stay in our sun-filled, beautifully renovated two-floor apartment in the heart of Westboro—one of Ottawa’s most walkable and vibrant neighbourhoods. Relax in the cozy Queen bedroom, cook in the fully equipped open-concept kitchen, and enjoy thoughtful touches from warm, responsive hosts. Steps to cafés, bakeries, restaurants, shops, gyms, groceries, and the LCBO, with the Civic Hospital just 6 minutes away. Pet friendly and designed to feel like home.

Top guest favourite
Flat in Potsdam
4.99 out of 5 average rating, 235 reviews

Beth's Place Potsdam - River - Pickleball- Hot Tub

Beth's Place- celebrating 12 years in business in 2026 - is a luxurious, self-contained apartment with a separate entrance for maximum privacy. It is spacious, tastefully furnished, and conveniently located within 1 mile of downtown Potsdam. Our guests can also enjoy the scenic Raquette River, with free kayaks available for use. For those seeking extra indulgence, the apartment also features a private hot tub – exclusively for our guests' use!

Top guest favourite
Flat in Ottawa
4.99 out of 5 average rating, 145 reviews

Whispering Timber Suite

Enjoy the peaceful calm of being surrounded by nature in Whispering Timber suite. You'll have exclusive access to the in-law suite of our home, complete with a bedroom (queen size bed), a sofa bed, a full bathroom and a small kitchen. The suite is located at the back of the home with it's own exterior entrance. Extra towels, sheets and comforters are provided, along with dishes and cookware in case you want to make a meal.

Popular amenities for Winchester apartment rentals