Vacation rentals in Windsor and Maidenhead

Cottage in Englefield Green

A grand entrance is showcased with a decorative wrought iron gate, featuring the year '1872' prominently displayed. The courtyard beyond is paved and lined with greenery, creating an inviting atmosphere. The brick architecture of the surrounding buildings adds historical charm.

4.88 out of 5 average rating, 179 reviews

Luxury 5* House Near Windsor Castle, Ascot, London

This Grade 11 listed Mews property was built in 1872 and offers contemporary, luxurious living space. Luxurious king size beds, beautiful bathrooms, abundant art and character; the properties look onto an ancient courtyard with fountain, secure behind private gates with parking. The location is exceptional. Windsor Great Park is a 10 min stroll away, and Windsor is 3 miles away, Wentworth Golf Club and Ascot are all within 6 miles. Central London is 35 minutes by train. Heathrow is 6 miles away.

4.88 out of 5 average rating, 64 reviews

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.

Home in Reading

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.

Apartment in Notting Hill

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).

5 out of 5 average rating, 114 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 in Hertfordshire

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.

4.97 out of 5 average rating, 140 reviews

Large glass doors open to a lush garden area, framed by greenery. A wooden dining table is set among plants, with chairs arranged around it. Natural light floods the indoor space, creating an inviting connection to the outdoors.

Home in Oxford

Beautiful , Oxford House, parking, EV charger

Our beautiful, very spacious Victorian town house is situated in a lovely quiet road favoured by academics and creatives. We have 4 large double bedrooms, comfortable and spacious living spaces and parking for 2 cars. We include crisp white linens and towels which are high temperature washed and the house is deep cleaned. Vibrant East Oxford has some of the best restaurants and cafes. We are a short walk from Magdalen Bridge, the Botanical Gardens, punting and the historic city centre.

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 in West Kensington

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.

4.99 out of 5 average rating, 102 reviews

An outdoor seating area features a circular table surrounded by dark wooden chairs. A barbeque grill stands nearby, and the surrounding garden is lush with greenery. The unique architecture of the property includes charming brick walls and vibrant green doors, framed by foliage.

Cottage in Chobham

The Coach House

The Coach House is a totally unique property, nestled in the peaceful surroundings of Chobham Common. Spread over two floors, this charming accommodation offers 2 bedrooms, 2 bathrooms, a sitting room, a dining room, a kitchen, & a utility room. There is also an outdoor seating area equipped with barbeque, perfect for unwinding. The quirky design & characterful features of this historic building add to its charm & make it a truly delightful place to stay.

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 in Didcot

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.

4.98 out of 5 average rating, 135 reviews

The bright and airy studio features vaulted ceilings with wooden beams. A king-sized bed is positioned beside large doors that open onto a small balcony. A cozy red sofa and coffee table are arranged in the sitting area. A decorative rug adds warmth to the wooden floor.

Guesthouse in Goring

The White House at Wayland

The studio is situated on a quiet private road overlooking an area of outstanding natural beauty, within easy walking distance to the riverside village of Goring-on-Thames. The self contained studio is a two story accommodation which is bright, airy and beautifully furnished with a private entrance. Breakfast basket and fresh ground coffee will be included

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

Apartments

Convenient locations with everyday essentials

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 Park24 locals recommend

LEGOLAND® Windsor Resort390 locals recommend

Ascot Racecourse181 locals recommend

Thorpe Park Resort216 locals recommend

Lapland UK21 locals recommend

Windsor, a Wyevale Garden Centre181 locals recommend

Other great vacation rentals in Windsor and Maidenhead

5 out of 5 average rating, 18 reviews

A spacious garden features a meticulously maintained lawn with striped patterns, bordered by dense greenery. A patio area is seen in the background, featuring seating under a white canopy, offering a peaceful space for relaxation.

Home in Windsor

Central Windsor, Large Garden, Games Room & Office

5 out of 5 average rating, 7 reviews

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.

Home in Berkshire

NEW Tornado Chase | Luxury 5 Bedroom Home

4.9 out of 5 average rating, 59 reviews

A modern kitchen is illuminated by natural light from skylights, featuring sleek cabinetry and stainless steel appliances. A dining set for four is positioned near windows, with light wood flooring enhancing the spacious feel. Neutral-colored curtains frame the windows.

Home in Greater London

3 bedroom house with parking

Apartment in Queen's Park

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

4.98 out of 5 average rating, 50 reviews

A lush garden setting is presented, featuring various greenery and flowering plants. Stone pathways lead through planted areas, while a table with chairs is positioned on a stone patio. A small shed is visible in the background among the vibrant foliage.

Condo in Greater London

Immaculate Maisonette on Fulham/Chelsea border

5 out of 5 average rating, 5 reviews

Condo in Colindale

Modern 3 Bedroom Apartment Next to London Museum

Shepherd’s hut in Old Windsor

A charming Shepherd's Hut is set on a spacious wooden deck, surrounded by colorful wildflowers. The hut's rustic exterior features a sloped roof and wooden doors, while outdoor seating is placed nearby, inviting relaxation in the natural surroundings.

4.92 out of 5 average rating, 13 reviews

Cosy Luxury Shepherd’s Hut near London & Windsor