Vacation rentals in Windsor and Maidenhead

An aerial view captures a vibrant riverside scene at dusk, showcasing a wide promenade with dining spaces illuminated by soft lights. The water reflects the warm glow from nearby establishments, while modern buildings rise in the background, creating an inviting urban atmosphere.

4.88 out of 5 average rating, 64 reviews

Spacious 4BR Home|FREE Parking & Wi-Fi|Garden

★Available for Business & Pleasure Bookings ★Accept Long & Short Stays ★FREE Wi-Fi & Parking ★Netflix & YouTube ♥Please message me with any questions! Enjoy your stay in this cozy, comfortable home! This house is located in the west of Reading, close to town centre. Take a stroll in Mcllroy Park, 30 acres Nature Reserve just behind the house. 1 Private parking & plenty of FREE parking on street. My place is close to Railway Station & Bus Stop. Excellent bus service to get you around Reading.

A bright bedroom is highlighted by a spacious bed dressed in soft linens and a textured throw. Shelving above the bed displays decorative items and plants. Two bedside lamps provide gentle illumination, while natural light enters through a window with clean white walls complementing the minimalist decor.

4.94 out of 5 average rating, 62 reviews

Stunning 2-Bed Notting Hill Portobello Apartment

Situated in Notting Hill / Portobello. The apartment is equipped with high speed Internet/WiFi and Netflix. The neighbourhood has an array of cafes, bars, restaurants, boutique & antique shops. All within a short walk and Portobello Market is just 300 yards. A well-conneced public transport with 3 nearby train stations, and local bus services to Hyde Park, Oxford Street, and Museums in South Kensington. Check-in time is from 3.30pm. Earlier Check-in subject to availbility (please enquire).

4.87 out of 5 average rating, 54 reviews

Condo

Lovely well-connected, spacious apartment

Our beautiful and spacious flat is located in South Harrow, Greater London. It’s a smoke free, please avoid smoke indoors. We are at the end of the high street very close to supermarkets and restaurants. Excellent transport and easy access to tourist attractions. A few minutes walk from Piccadilly line Underground, South Harrow station, with easy access to Heathrow airport (express bus) and Wembley stadium (one stop by train). We don’t have a designated parking space, but free street parking.

5 out of 5 average rating, 115 reviews

A serene bedroom features deep navy walls and large windows that allow natural light to fill the space. A minimalist mirror is mounted on one wall, and a stylish radiator creates a cozy feel. A low bed with a patterned duvet and a potted plant add to the decor.

Cottage

Upscale Bright Boutique Cottage Central St Albans

Our Cottage has been renovated from ground up and we are thrilled to present our "good life home". An experience of upscale casual elegance. Opting for a clean and uncluttered energy you will find our home equipped for the most discerning guests. A fully stocked gourmet kitchen with a Nespresso Citiz & Milk, a gas range cooking, Wall-to-wall window for natural light and a cosy outdoor lounge. The Living space displays contemporary décor, colours are serene and neutral and comfort is standard.

A modern studio space is highlighted by a well-equipped kitchen featuring cabinetry and a microwave. A round table with two chairs occupies a corner, while a large mirror enhances the room's sense of space. Natural light filters in through the window, illuminating the warm wood accents.

4.8 out of 5 average rating, 10 reviews

Nice studio in a top location at 3rd floor

Superb studio in a premium location. ☆Baker Street, Marylebone area Please, note that this apartment is located on the 3rd floor of an original period building and there is no elevator/lift, please bear this in mind if your luggage is very heavy. Perfect for tourist and business trips. One set of towels per guest and linen are provided. Feel free to send me a message if your dates are not available on the calendar. I will do my best to help you. Looking forward to hosting you!

A modern bathroom features a sleek walk-in shower enclosed by glass panels. A compact wall-mounted sink is positioned above a minimalistic toilet. Neutral-colored tiles and a well-lit mirror enhance the space, while shelves hold toiletries for convenience.

4.9 out of 5 average rating, 70 reviews

Number 2. Regents Park Apartments

Close to The Regents Park, this apartment is ideally situated for exploring London. With 3 underground stations within walking distance, plus the excellent Central London Bus network, getting to all popular attractions couldn't be easier or quicker. This spacious 2 bedroom apartment is situated above The Queen's Head & Artichoke Bar/Restaurant and has been recently converted into a stylish Airbnb rental. This special place is close to everything, making it easy to plan your visit.

4.89 out of 5 average rating, 47 reviews

A modern kitchen area is visible, featuring two green bar stools situated at a countertop. A cozy green sofa with a yellow cushion is positioned beside the kitchen. Large windows allow natural light to fill the space, while a leafy plant adds a touch of greenery.

Condo

Spacious, Designer one bedroom flat in Kensington

Enjoy a stylish experience at this centrally-located place. I am renting out my beautiful and recently renovated apartment in West Kensington. The flat has everything you need to enjoy your stay. The king size bed is what you need to sleep well. Location: peaceful, safe and quiet one-way road. Tube: 5 min walk District line (West Ken); 10 min walk Piccadilly Line (Barons Court Station) so you are 20 min from the Central London. Supermarket is 2 min walk, lots of bars and cafes.

A modern bathroom features a bathtub with a shower above, complemented by a white vanity with a sink. A round mirror hangs above the sink, and decorative tiles create an appealing pattern on the floor. A window provides natural light to the space.

4.93 out of 5 average rating, 14 reviews

Cosy, comfortable 1 bed flat in Streatham

Our stylish, bright and airy little flat in leafy south London is the perfect spot for a trip to the capital. With a large bedroom and spacious living room/diner it’s got everything you need to feel at home. There is a large sofa bed in the living room, meaning it’s perfect for a weekend trip with pals, or little ones. We also have a desk/makeup space in the bedroom, a dining table to seat 4 and a breakfast bar in the kitchen.

4.97 out of 5 average rating, 129 reviews

A private hot tub for four people is positioned on a wooden deck. The hot tub cover is partially open, revealing clear, inviting water. The surrounding area features wooden fencing and steps leading down to the garden, with greenery visible beyond.

Cabin

Little Cowdray Glamping - The Log Cabin

Little Cowdray Glamping Log Cabin is a self contained mini home, with a comfy King size bed, 2 Single Bunk beds, cooker, oven, microwave, bathroom with shower, log burner, and central heating. It has all the necessary accessories and utensils you will need for your stay. The Cabin has it's own Garden area, hot tub, and includes parking and outdoor seating. There is a Gas BBQ should you wish to dine outside or star gaze.

4.96 out of 5 average rating, 52 reviews

A modern kitchenette is equipped with a stainless-steel sink, a red kettle, and a two-ring hob. Natural light enters through a nearby window, while a white door provides access to the outside. The cabinetry features a light finish, enhancing the bright environment.

Guest suite

Self Contained near Didcot Station

Self-contained studio just 5 min from Didcot station. It's perfect for travelling to Harwell, Culham & Milton Park. Oxford is just 12 mins away by train, 15 mins to Reading. Short walk to town centre with all amenities, including the Orchard Shopping Centre, cinema and restaurants. Equipped with a kitchenette & ensuite shower room, Virgin broadband/TV. This is a great 'home from home' for one.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Windsor and Maidenhead vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Windsor and Maidenhead's top sights

Thorpe Park12 locals recommend

LEGOLAND® Windsor Resort174 locals recommend

Ascot Racecourse81 locals recommend

Thorpe Park Resort50 locals recommend

Lapland UK21 locals recommend

Windsor, a Wyevale Garden Centre181 locals recommend

Other great vacation rentals in Windsor and Maidenhead

A charming two-story brick house is set within a lush garden, featuring well-maintained greenery and colorful flower beds along the front. A gravel path leads to the entrance, and tall trees provide a natural backdrop to the property.

4.81 out of 5 average rating, 26 reviews

Airy 4-bedroom detached house with gardens/patios

A modern kitchen features a large central island with four black high stools. Stainless steel appliances, including an oven and a hood, are visible amid sleek white cabinetry and blue accents. Natural light enters through nearby windows, illuminating the glossy tiled floor.

5 out of 5 average rating, 8 reviews

NEW Tornado Chase | Luxury 5 Bedroom Home

Double doors open to a private balcony, featuring a small table and two green chairs. A cozy sofa in bright green is positioned nearby, complemented by a side table with a coffee cup and a kettle. Natural light fills the space, creating a welcoming atmosphere.

5 out of 5 average rating, 6 reviews

Chic 2Bed w/Balcony/10min FR Notting Hill

A bright living area is presented with large windows and warm wood flooring. A round glass dining table is surrounded by stylish chairs, while a modern blue sofa offers comfortable seating. A tapestry and artwork adorn the walls, adding character to the space.

5 out of 5 average rating, 9 reviews

Fabulous 2 Bed 2,5 Bath Apartment next to Park

A stylish lounge area features a comfortable L-shaped sofa adorned with colorful cushions. Light streams through large windows, illuminating the space. A modern coffee table sits on a patterned rug, while a dining table is visible through the patio doors leading to the private garden.

4.78 out of 5 average rating, 117 reviews

Stunning 1BD Basement Flat with Garden, Camden

5 out of 5 average rating, 16 reviews

Premium - 4 bedroom house with garden and balcony

4.98 out of 5 average rating, 51 reviews

A spacious living area features a neutral color palette with two sofas and armchairs arranged around a coffee table. Natural light enters through large windows, and a decorative mirror reflects the space. A vibrant area rug adds warmth, complementing the overall decor.

Condo

Immaculate Maisonette on Fulham/Chelsea border

A modern kitchen is showcased with a black countertop and glossy black tiled backsplash. Appliances include a microwave, kettle, and toaster, alongside a gas stove and coffee maker. Cabinetry in neutral tones complements the overall sleek design.