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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, 155 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 modern open-concept kitchen and living area is showcased, featuring a large island with seating for three. Sleek white cabinetry and stainless steel appliances are present, with a spacious seating area visible in the background. Natural light enters through multiple windows, enhancing the bright atmosphere.
Flat in Westboro
4.99 out of 5 average rating, 255 reviews

Lovely spacious&modern one-bedroom unit in Ottawa

Centrally located in the upscale and trendy neighborhood of Westboro village, this quiet and bright one-bedroom apartment is only a few minutes away from downtown Ottawa and its tourist attractions by car or by public transportation, and a few steps away from all restaurants and boutiques that Westboro has to offer. Vibrant community with every amenity at a walking distance: restaurants,groceries, liquor store,banks,medical center,pharmacy,hospital,public transportation,EV charging station, etc.

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, 219 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.

Guest favourite
A light-filled dining area features a round table surrounded by four white chairs. A soft red area rug complements the decor, while a chandelier hangs above. Natural light streams through a window adorned with sheer curtains, illuminating the simple yet inviting space.
Flat in Chelsea
4.91 out of 5 average rating, 366 reviews

Your Old Chelsea/Gatineau Park Pied-à-Terre

Beautiful, well appointed 2 bedroom apartment with fully furnished kitchen in charming Old Chelsea village. You will be 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.

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 kayaks available for use. For those seeking extra indulgence, the apartment also features a private hot tub and courtyard. There is a shared igloo, putting green, pickleball court, and beach area.

Superhost
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
4.94 out of 5 average rating, 151 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, 105 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
The home entrance features a welcoming door with decorative windows. Surrounding the entrance are vibrant flowers and foliage, complemented by several garden stones. Four metal chairs are positioned near the entrance, providing a quaint spot to relax in the lush greenery.
Flat in Cornwall
5 out of 5 average rating, 213 reviews

Basement Bliss!

Welcome to Cornwall! Nestled in a quiet north end Cornwall neighbourhood, just around the corner from the Ontario Hockey Academy and within close proximity to all city amenities (sports facilities, big box stores and restaurants). My home is 3 kilometres south of the 401, 3 kilometres north of the USA border and 25 minutes west of the Quebec/Ontario border. Key-less entry through the side door. Come and go as you please. Short-term rental available. Message for further details.

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, 167 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
A modern kitchen is equipped with a large island featuring high stools. Sleek appliances, including a refrigerator and stove, are complemented by minimalist cabinetry. Natural light filters through a nearby window, enhancing the clean design. A decorative plant adds a touch of warmth.
Flat in Chelsea
4.97 out of 5 average rating, 119 reviews

Dream apartment comforting & relaxing

The bike path is accessible directly from the parking lot. Only a few minutes from the Voie Verte, Larrimac Golf and Tennis Club, Ski Camp Fortune, Great Canadian Bungee and the gateway to Gatineau Park. The apartment’s convenient location in Chelsea makes it a comforting destination in many ways. Come and explore this small village which has lots to offer such as many art galleries, boutiques, cafés and gourmet stops. Relax and unwind at Nordik Spa Nature. CITQ. #318284

Top guest favourite
Flat in Gatineau
4.93 out of 5 average rating, 123 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.

Popular amenities for Winchester apartment rentals