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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

Le 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
Flat in Potsdam
4.99 out of 5 average rating, 210 reviews

Beth's Place II Potsdam-Pickleball, River & HotTub

Beth's Place II - on the river - is a private apartment above our garage, with a separate entrance and a great private outdoor space with a hot tub. The tastefully furnished cozy apartment provides an ideal relaxing setting with beautiful river views. Outfront is our new pickleball court & putting green for our guests' enjoyment! We are located just 1 mile from downtown Potsdam, 1 mile from Clarkson, 2 miles from SUNY Potsdam, and 10 miles from SLU and SUNY Canton. We know you'll love our place!

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

La loop - CITQ 321091

NON FUMEUR Recharge auto NIVEAU 2 ($ à discuter). Appartement privé et entrée privée. Parking sur place. Cuisine complète, salle de bain douche. Lit queen avec couette-plume de qualité. Lit avec housse anti-acariens. Buanderie dans le logement Animaux permis (avec approbation). Netflix, Disney et Prime inclus. Internet haute vitesse. Caméras extérieures, détecteur de fumée et de monoxide de carbone, extincteur, serrure à code unique, diverses issues de secours, éclairage extérieur, etc.

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, 367 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.

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, 152 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, 214 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, 168 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, 310 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, 120 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 Westboro
4.94 out of 5 average rating, 154 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 Ottawa
4.99 out of 5 average rating, 148 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