House holiday rentals in Windsor

A bright living area features a blue sectional sofa positioned beside a modern, round coffee table. Natural light enters through large windows, illuminating the space. A sleek fireplace and a mounted television are visible along the white brick wall, creating a cozy gathering spot.

4.83 out of 5 average rating, 286 reviews

Walkerville Charm Home

This stunning 4 bedroom, 6 bed home is dressed to impress! We have spared no detail to ensure your comfort, including: *4 Casper queen beds; * 2 Casper full beds; * a Weber gas BBQ; * lightning fast WIFI connection; * a 50-inch smart Samsung TV in the living room; * a 55-inch smart Samsung TV on the upper floor; * a large formal dining room; * an open concept dining/living/sitting space which can comfortably seat 10 people; * a kids' korner for playtime; * and+++ *Note: Hot tub not available

4.97 out of 5 average rating, 143 reviews

A private outdoor patio features a hot tub surrounded by wooden fencing and a pergola. Comfortable seating is provided by two chairs, with a BBQ grill situated nearby. Natural light filters in through the overhead structure, enhancing the relaxing atmosphere.

Home in Riverside

Perfect hideaway with a hot tub and a fireplace

Find your sanctuary at Little River Retreat. Bordering parks, with luxe vibes, a crackling fireplace, and a dreamy hot tub. Enjoy a walk or bike ride through beautiful parks and beaches, including the 10 km+ Ganatchio Trail and Sandpoint Beach (both 5 minutes away). In under 45 min, find yourself in wine country, or for nature lovers, Point Pelee National Park. WFCU Centre 3 min away. Caesars Windsor, tunnel & bridge to USA 10-15 min away. Detroit airport approx 45 min, new battery plant 9 min

4.94 out of 5 average rating, 120 reviews

An outdoor dining area is set with a red table and chairs under a retractable awning. The grey exterior of the lodge is framed by a manicured lawn and wooden fencing, creating a secluded and private atmosphere. Natural light enhances the inviting space.

Home in South Windsor

Luxury 2BR home with high ceilings and BBQ w/patio

Labelle Lodge invites you to this bright home with 2 spacious bedrooms and a living area with high ceilings and tons of natural light. Nestled amongst majestic trees, the serene getaway is just 7 minutes away from the US border. Conveniently located near EC Row, you’re minutes away from the Riverside and the entertainment district. Enjoy high speed internet and two smart TVs with all your streaming apps. Indulge in the outdoor dining area and experience the tranquility of South Windsor.

4.8 out of 5 average rating, 218 reviews

Home in Riverside

Cozy & Spacious Family Home w/Fireplace & Sunroom!

*HEATED POOL IS OPEN APRIL 1 - OCT 31* Welcome to Windsor’s largest and coziest stay! This gorgeous home blends modern design with comfort, featuring an inviting sunroom with soaring ceilings and natural light, perfect for morning coffee or quiet evenings. The chic decor creates a stylish, yet homey feel :) Unwind in a private backyard oasis with a 15x30, 8’ deep, in-ground oval pool with a brand NEW heater and BBQ lounge! Our backyard designed for a unique and relaxing family experience!

An open living area is featured, showcasing a dining table with black chairs and a modern design. A corner sectional sofa and large wall-mounted TV are visible. Light-colored walls and a wood-like floor create a seamless flow between the spaces.

4.88 out of 5 average rating, 162 reviews

Beautiful 3Bedroom 2Bath Home free parking&laundry

Welcome to our spacious Midtown home away from home featuring 2 floors of living(main & upper stairs) that have been beautifully updated offering 3 bdrms 2 full baths, 2 living rms w/65”&55” TVs w/Netflix. Full kitchen w/stainless appliances, granite counters, covered front porch for enjoyment, fenced backyard. On a quiet block, close to transit, shopping, restaurants, ECRow, 401&Windsor-Detroit Tunnel. Private drive Ideal for families, out of town workers or large groups. Come & Relax!

A modern living area is featured, furnished with a soft gray sofa and a stylish coffee table. A wooden sideboard is placed against the wall, complemented by decorative items. Light walls enhance the spacious feel, while a chandelier adds subtle brightness to the room.

4.94 out of 5 average rating, 192 reviews

Charming Old Walkerville 2-Bedroom Luxury Suite

Located in the heart of Old Walkerville. Steps from restaurants, bars, shops, parks and the waterfront. A bright and comfortable main level suite that's part of a large duplex home. Perfect for relaxing visitors or working professionals. There are two spacious bedrooms with queen beds, closet and drawer storage. The grand room and kitchen are fully equipped just like home. The deck and yard space are available for fresh air fun and entertainment. There are 2 parking spots on site.

A modern kitchen features sleek white cabinetry and stainless steel appliances. A quartz island is complemented by a decorative tray with coffee essentials. A wall clock adds a touch of functionality, while a bowl of green apples offers a fresh accent.

4.99 out of 5 average rating, 122 reviews

Luxurious 3BR, King Bed, Ensuite. Perfect Stay!

Welcome to our 2 year old, modern and bright 3-bedroom, 3-bathroom townhome in East Windsor! Our home features a spacious layout with a clean and contemporary design, making it the perfect spot for your next getaway. The king-sized bed in the master bedroom comes with an ensuite bathroom for added privacy and convenience. Great location, close to WFCU Centre. Perfect for family vacations, weekend getaways, or business trips. Experience the best of East Windsor from our cozy home!

A private outdoor space is highlighted by a covered gazebo, featuring a hot tub and relaxing seating options. Lush greenery surrounds the area, complemented by well-placed planters. Natural light filters through, creating a soothing environment for leisure and relaxation.

4.84 out of 5 average rating, 129 reviews

Couple's Romantic Retreat with hot tub, fire pit.

Romantic and soothing discreet hideaway. Come to relax, reunite and enjoy the night. This beautiful unit features: -private backyard Oasis with Hot tub, cedar Gazebo, outdoor Tv and sound bar, accent lighting, bbq and fire pit. -king size bed; -couple's spa shower; -massage table -fully stocked chef's kitchen; -private garage parking; -nearby parks and trails; -plus all of the comforts of being in the city. Everything you need to enjoy a restful and relaxing weekend away.

A spacious backyard is presented, showcasing a hot tub situated on a concrete pad. Green grass lines the space, complemented by wooden fencing and ambient lighting. A small tree is visible in the corner, and utility lines are present in the sky against a colorful sunset backdrop.

4.96 out of 5 average rating, 114 reviews

Modern Walkerville Gem | HotTub & Cozy Backyard

This beautifully renovated townhome combines luxury and comfort. Cook in the spacious kitchen with new stainless steel appliances and granite countertops, dine at the custom live-edge wood table, and enjoy your favorite shows on a 65" Roku TV with Sonos soundbar. Relax in the deep bathtub or retreat to the backyard oasis featuring a large deck, hot tub, natural gas BBQ, patio furniture, and beautiful lighting. Rest easy on two plush queen beds in this stunning retreat.

4.89 out of 5 average rating, 227 reviews

A spacious living area with modern furnishings is visible. A dark sectional sofa and a matching ottoman are arranged near a large window, with natural light illuminating the space. A mounted television is positioned on the wall opposite a dining table set with plates and glasses.

Home in Downtown Windsor

Downtown 2 Bed 1 Bath Unit w/ Free Parking

Welcome to our updated 2 bed 1 bath upper unit in downtown Windsor! With a fully equipped kitchen including stainless steel appliances & quartz countertops and a 65in TV with Netflix in the living room, this apartment has everything you need for a comfortable stay. Located near transit, shopping, and restaurants. This location is on a quiet block just minutes walk to the heart of downtown. Book now for a cozy and convenient home-away-from-home experience!

4.97 out of 5 average rating, 213 reviews

A spacious living area features a sectional sofa and a coffee table, with soft lighting provided by a pendant light. A dining table with white chairs sits nearby, and an image of a bridge adorns the wall, contributing to a modern and inviting atmosphere.

Home in Forest Glade

Shalom - Modern Spacious Home, 4BR + 4Beds + 3BA

A beautifully renovated house with a modern finish that lies within Forest Glade, East Windsor Ontario Canada. The 4 bedrooms, 3 bathroom and sofa bed house is plentiful in space for guests and is perfect for families, business travellers, and front line workers. During your stay, we provide the essentials from toilet paper to towels and linens in order for your stay to be as trouble-free as possible. With that being said, we welcome you to come

A bright living room features two modern sofas facing a coffee table, with a large window dressed in sheer curtains allowing natural light. A functional bar area with stools is visible in the background, connecting to the kitchen, while light wood flooring enhances the space.

4.94 out of 5 average rating, 121 reviews

Family-Sized 3BR • 5 Beds • Near Downtown

Stay close to downtown Windsor in our 3-bedroom home, with an extra bedroom/living space in the finished basement. We've got 5 beds (2 queens, 3 twins, and a sofa bed in the basement), plus a TV in every bedroom. It's pet-friendly with a big backyard. Ideal for families – we've got a high chair and playpen. Kids can have their own space in the basement with a big TV. Enjoy a convenient and comfortable stay!

Popular amenities for Windsor house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.86 out of 5 average rating, 99 reviews

A two-story cottage with a light grey exterior is showcased, featuring a welcoming front porch with white railings. A spacious yard surrounds the home, with a gravel driveway leading up to it. Lush green grass complements the serene environment.

Home in Amherstburg

Cottage Escape by the Water

4.86 out of 5 average rating, 22 reviews

A heated sports pool, surrounded by a spacious patio area, is complemented by comfortable seating options including loungers and umbrellas. A contemporary pool house with large windows is visible in the background, featuring a clean design that enhances the outdoor space.

Home in Belle River

The Grand River Retreat. Pool/ hot tub avail Sep

The exterior of a single-story home is shown, featuring a spacious driveway lined with paving stones. Lush greenery, including a large evergreen tree and manicured shrubs, frames the entrance, which includes a blue door and large front windows under a lightly clouded sky.

4.59 out of 5 average rating, 34 reviews

Luxury at its finest (Windsor) Swimming Pool

A two-story brick house is framed by lush green landscaping. Large front windows allow natural light to fill the interior. A driveway leads to a two-car garage, while decorative stones and various shrubs add visual interest to the front yard.

5 out of 5 average rating, 3 reviews

Warm&Bright Upper Unit | Pool+Coffee+Big Driveway

4.98 out of 5 average rating, 40 reviews

A spacious living room features a large sectional couch and a coffee table, with a television displaying a beach scene. Bright natural light enters through the window, which is complemented by light curtains. The polished wooden floor adds warmth to the space.

Home in Riverside

Spacious Family Getaway w/ Pool -Sleeps 12 - 2 TVs

4.92 out of 5 average rating, 118 reviews

The exterior of a two-story brick home features large windows framed by wooden shutters. A stone pathway leads to the entrance steps, which are flanked by neatly landscaped flower beds and ornamental plants in decorative pots. The entrance is inviting, with a warm color palette.

Home in Malden

The Ambassador Estate Inn

4.98 out of 5 average rating, 95 reviews

A spacious outdoor pool is highlighted under clear blue skies. Several lounge chairs are positioned poolside, providing ample seating for relaxation. The surrounding area features well-maintained greenery and a fence that encloses the space.

Home in Belle River

Belanger Air BnB

A modern retreat is highlighted by a sleek, heated pool reflecting the evening sky. Floor-to-ceiling windows provide glimpses of illuminated indoor spaces, while a rooftop terrace is accessible. A landscaped patio is bordered by a wooden fence, offering privacy.

4.68 out of 5 average rating, 25 reviews

Architectural Gem | Direct-Entry Pool

Weekly house rentals

A cozy living area features comfortable seating with dark leather chairs and a sectional sofa. A glass dining table is set for four, with a view of a television and a doorway leading to a bedroom in the background, complemented by soft wall colors.

4.82 out of 5 average rating, 44 reviews

Paradise Home - Home Away From Home

5 out of 5 average rating, 6 reviews

Two bedrooms full house

A well-maintained brick house is set on a landscaped front yard featuring manicured grass and various shrubs. A spacious driveway leads to an attached garage. Large windows allow natural light to illuminate the home, surrounded by nearby trees and a pleasant neighborhood.

4.63 out of 5 average rating, 8 reviews

TEC-East BSMT APT 55inchTVSports CBL Office Space

4.87 out of 5 average rating, 30 reviews

Private Clean Suite Getaway |Work & Relax in Style

A living area is displayed with modern furniture, including a beige sofa and a glass coffee table. A large plant adds a touch of greenery beside a dark television stand. The open layout connects to a bright kitchen, featuring white cabinetry and stainless steel appliances.

4.68 out of 5 average rating, 34 reviews

Cozy 2Bdrm Entire Home in East Windsor

4.9 out of 5 average rating, 60 reviews

A welcoming exterior view of a charming house features a covered front porch with wooden railings. The entrance is highlighted by a white door, flanked by bouquets of colorful flowers in hanging pots. Lush green landscaping surrounds the stone pathway leading to the porch.

Home in Downtown Windsor

Cozy corner home in Windsor

4.75 out of 5 average rating, 40 reviews

A bright living room is filled with natural light from tall windows. Two pieces of abstract artwork adorn the wall above a dark coffee table, which is surrounded by light-colored seating. Textured rugs cover the floor, adding warmth to the space.

Home in South Windsor

Charming urban retreat

4.83 out of 5 average rating, 29 reviews

Chic and Cozy Walkerville Retreat! 3beds, 2 Baths

Private house rentals

5 out of 5 average rating, 14 reviews

Stylish 4BD House | Mins To DT | Sleeps 8

4.93 out of 5 average rating, 30 reviews

Clean 4 BR Home with Karaoke and Arcades

A dining area features a round table set with placemats, positioned near a large window. Black chairs are placed around the table, offering a view of the traffic and street activity outside. Natural light enters through the window, creating a functional space.

5 out of 5 average rating, 6 reviews

Perfect place to stay

5 out of 5 average rating, 7 reviews

4B 3.5B New Listing! Dream Home

4.98 out of 5 average rating, 42 reviews

The historic brick duplex displays a classic architectural style with a welcoming porch and three prominent front windows. Lush greenery surrounds the entrance, enhancing the outdoor space. A charming balcony above offers additional character to the building's facade.

Home in Henry Ford

Renovated cozy home for working professionals

A living room is shown with light-colored walls and hardwood flooring. A beige sofa is positioned in the center, with two patterned yellow chairs flanking a simple wooden coffee table. A framed artwork with a floral design hangs above the sofa, and greenery is visible from a nearby window.

5 out of 5 average rating, 25 reviews

Spacious 3-Bed Home in S windsor

5 out of 5 average rating, 40 reviews

The exterior of The Stone Cottage is highlighted by its striking stone façade and black shutters. A covered porch extends across the front, supported by decorative beams. Potted plants flank the entrance, while a brick-paved walkway leads to the entry door, enhancing the inviting atmosphere.

Home in Amherstburg

The Stone Cottage

A well-appointed bedroom features a wooden sleigh bed adorned with decorative cushions. Two bedside lamps provide soft illumination on matching nightstands. A patterned area rug lies on the warm-toned wooden floor, adding comfort and style to the space.