Holiday houses in Windsor and Maidenhead

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Top-rated holiday rentals in Windsor and Maidenhead

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Top Guest favourite
The charming Victorian Lodge features a classic brick exterior with white trim, framed by lush greenery. Two inviting front windows and a central doorway are surrounded by decorative flower pots. A gravel pathway leads to the entrance, highlighted by an expansive tree nearby.
Cottage in Windsor
4.99 out of 5 average rating, 102 reviews

Gorgeous CountryCottage overlooking Windsor Castle

The Victorian Lodge (1876) is a charming & quintessentially English country cottage on a private estate once owned by King Henry 8th. It sits right beside Windsor Great Park, at the entrance of a long driveway to Little Dower House, where the owners of the Lodge live. The private gardens and stunning view at the Victorian Lodge provide the perfect setting for a small intimate wedding. Whilst the romantic gardens within the Little Dower House estate provide an ideal venue for larger weddings.

Top Guest favourite
The charming exterior of a Victorian terraced home features a white door framed by climbing greenery. Flower boxes filled with pink and white blooms adorn the windows, while a small bench sits beneath a decorative wrought iron fence.
Cottage in Bray
4.94 out of 5 average rating, 127 reviews

Charming terrace in the heart of Bray village

Our lovely victorian terraced home is perfectly situated for all the fine dining that the charming village of Bray has to offer. The Michelin 3-starred Waterside Inn and Fat Duck are a few mins walk away as are the Crown Inn, Hinds Head and Caldesi. Stroll 15 mins more and you’ll find the recently renovated Monkey Island Estate. A short drive and you can be at either Ascot or Windsor Races, Cliveden House, Legoland, the village of Cookham or the beautiful river Thames towns of Marlow or Henley

Top Guest favourite
The cottage's serene garden is shown, featuring a stone patio with a wooden dining set surrounded by greenery. Sunny skies illuminate the exterior of the cottage, with trees and shrubs providing privacy and a peaceful atmosphere.
Cottage in Bray
5 out of 5 average rating, 145 reviews

A Hidden Gem

A character cottage, tucked away, in the heart of gastronomic Bray - renowned for its Michelin-starred restaurants: The Waterside, The Fat Duck, the Hind's Head and Caldesi, all within easy walking distance of the cottage. Lych Cottage is a two-bed semi-detached property, completed to a high standard. It provides a stylish place to stay for those wishing to enjoy the comforts of home whilst availing themselves of the local amenities. The first night's stay includes a continental breakfast.

Top Guest favourite
A cozy sleeping area features a spacious bed with neutral bedding against a softly colored wall. A small armchair and a light-colored rug complement the wooden flooring. Wall-mounted shelves display framed images, and a small closet provides additional storage.
Guest suite in White Waltham
4.94 out of 5 average rating, 444 reviews

Completely separate self-contained studio flat

Self-contained double room with en-suite shower room and kitchen area. Private access and parking. Completely private stand-alone studio but part of our home. Suitable for professional person/couple for short let periods. Ideal Monday-Friday but good for weekends to visit local area too. Free wi-fi, TV. A car is essential. Located in White Waltham village just outside Maidenhead. Easy access to Junction 8/9 of M4 and Maidenhead station. Also handy for Windsor, Henley, Ascot, Reading

Top Guest favourite
A detached house with a brick and stucco exterior is visible. A paved driveway accommodates two vehicles, including a dark sedan and a blue SUV. Landscaping features a short hedge and a gravel area, framed by blue skies and a few scattered clouds.
Guesthouse in Berkshire
4.97 out of 5 average rating, 152 reviews

Self-contained studio Wokingham

A self-contained newly build 20 m2 studio with separate entrance and parking. The studio is comprised of an en-suite bathroom, a super-king bed, a tall boy and a work desk. A kitchenette just next to the room with fridge freezer, microwave, kettle, toaster, coffee machine, washing machine and a tumble dryer. “The kitchenette doesn’t have a stove or an oven.” The studio is brand new and built to high standards. The studio is a 15 minutes walk to Wokingham train station and town centre.

Guest favourite
The exterior of the Grade 11 listed Mews property is shown, featuring a combination of brick and tile. A spacious courtyard is visible, bordered by trees and carefully arranged pathways. Private gates provide security, while the surrounding landscape includes greenery and open sky.
Home in Englefield Green
4.93 out of 5 average rating, 111 reviews

5* Boutique House Nr Windsor Castle, Ascot, London

This Grade 11 listed Mews property was built in 1872 and offers contemporary, five star living space. Luxurious king size beds, beautiful bathrooms, abundant art and character; the property 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 within 6 miles. Central London is 35 minutes by train. Heathrow is 6 miles away.

Top Guest favourite
A cozy studio space is showcased, featuring a king-size bed with light bedding and decorative pillows. Natural light enters through large windows, illuminating the comfortable seating area with a patterned rug. A small bookshelf adorns the wall, adding a touch of warmth to the inviting atmosphere.
Apartment in Datchet
4.98 out of 5 average rating, 233 reviews

Stylish Studio-Walk to Windsor/Eton/Thames/Parking

Welcome to Crail Cottage in Datchet. Surrounded by beautiful greenery, there is plenty of wildlife and the River Thames is just behind the house. Take a walk to Windsor and Eton via the home park or the riverside. You can even walk to Eton through the school grounds from here. Our little studio is freshly decorated and welcomes you to stay. There is a new addition which is a King size bed with Hypnos mattress that will guarantee you a good night sleep. Perfect to relax after a busy day.

Top Guest favourite
The exterior of the modern annexe is showcased, featuring large glass doors that allow natural light to fill the interior. A spacious balcony is visible above, bordered by glass, and wooden furniture is arranged on the terrace, ideal for outdoor relaxation.
Home in Tetsworth
5 out of 5 average rating, 349 reviews

Luxury self-contained Annexe with balcony Jacuzzi

Luxury self-contained annexe on the edge of the Chilterns, situated in the peaceful countryside which can be enjoyed from the hot tub, yet only 5 mins to the M40, 15 mins to Oxford Park & Ride & 15 mins to the station with trains to London taking 45 mins. It is the perfect place to relax with cosy lounge, wood burning stove, bespoke kitchen & underfloor heating. Upstairs features a super-king sized bed, seating area, luxury wet-room with underfloor heating, balcony and Jacuzzi.

Top Guest favourite
The open-plan living area features two comfortable sofas arranged around a wooden coffee table, with decorative cushions. A modern kitchen is visible in the background, showcasing grey cabinetry and contemporary appliances. Natural light enters through large windows overlooking a private outdoor space.
Apartment in Wokingham
4.95 out of 5 average rating, 168 reviews

"Koti" Grade II Listed Flat in Wokingham

Newly renovated Grade II listed, two bedroom flat. Sole use. Own private entrance and check in. Historical detail combined with contemporary furnishings creates a stunning base from which to explore the local area. Three minute walk to the station, excellent train links. Easy access to the A329 and motorways. 30 mins to Heathrow. Parking is on road in front of the property on a one way street. Hosts live below so always available for any assistance or local information.

Top Guest favourite
A cozy corner of the apartment features a decorative fireplace with an ornate mantle. Handwritten notes are displayed above the mantle, and a wooden desk is positioned nearby. A vintage chair and a chandelier add to the room's charm, with warm light filtering through a window.
Condo in Hertfordshire
4.99 out of 5 average rating, 139 reviews

Wizards Retreat - 8 Mins to HP Warner Bros Studio!

Welcome to ‘The Wizard’s Retreat’ This Airbnb is perfectly located just an 8-minute drive from Warner Bros. Studios, making it the ideal stay for fans visiting the Harry Potter Tour. There's wizard books to read, games to play & spooky potions to see! Whether it’s a spellbinding weekend with friends, a cosy couple’s getaway, or a family adventure, The Wizard’s Retreat has been designed to capture the wonder and excitement of the wizarding world for all to enjoy!

Guest favourite
A modern living area features large floor-to-ceiling windows, providing abundant natural light and showcasing expansive views. A plush sofa complements a sleek dining table set for six. Light wooden floors enhance the spaciousness, while greenery adds a touch of nature.
Condo in Bracknell
4.97 out of 5 average rating, 136 reviews

Luxury Penthouse with Huge Balcony

Take a break in our luxurious penthouse. The enormous south-west facing balcony offers panoramic views of the sunset each evening, making it the perfect spot to relax after a day. The interior is bright and modern, with floor-to-ceiling windows and sliding doors that fill the space with natural light. The fully-equipped kitchen has everything you need to prepare meals, and the living room is outfitted with premium audio (Sonos) and TV for your entertainment.

Top Guest favourite
A cozy sitting room is featured, showcasing a comfortable armchair and a large coffee table adorned with various books and decorative items. A warm fire burns in the fireplace, and built-in shelving lines one wall, filled with a diverse selection of books.
Cottage in Warfield
4.98 out of 5 average rating, 309 reviews

Luxury 2 bedroom cottage

Luxury Cottage at Hayley Green A charming, character-filled retreat for up to 4 guests in a peaceful semi-rural setting. Designed for comfort and relaxation, it’s ideal for couples, families, or friends. Enjoy a well-stocked library if you prefer to stay in. Perfectly located: 6 mins to Lapland Ascot 9 mins to Legoland 11 mins to Ascot 16 mins to Windsor & Wentworth 30 mins to Henley-on-Thames Under 1 hour by train to London via nearby Bracknell station

Popular amenities for Windsor and Maidenhead holiday rentals

When is the best time to visit Windsor and Maidenhead?

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Frequently Asked Questions

  • What are the best places to stay in Windsor and Maidenhead?

    Windsor and Maidenhead has inviting neighborhoods near the river and around the historic town center. Staying in areas such as Windsor’s central district or Maidenhead’s riverside neighborhoods gives you easy access to local shops, parks, and landmarks.

  • What are the best things to do in Windsor and Maidenhead with kids?

    Families can explore Windsor Castle, visit LEGOLAND Windsor Resort, and walk along scenic riverside paths. The area has parklands and hands-on museums that make for interactive outings.

  • What are some of the best things to do in Windsor and Maidenhead?

    Windsor and Maidenhead has historic sites like Windsor Castle, scenic strolls by the Thames, and vibrant local markets. Exploring Eton College or relaxing in Windsor Great Park are often recommended experiences.

  • How is the weather in Windsor and Maidenhead?

    Windsor and Maidenhead has mild winters around 37–48°F (3–9°C) and warmer summer days near 58–75°F (14–24°C). Rain is spread across the year, so a light waterproof jacket is handy for exploring outdoor sites.

  • What are the best places to visit in Windsor and Maidenhead?

    Explore Windsor Castle, stroll through Windsor Great Park, and visit the charming streets near Eton College. Maidenhead’s riverside and the town’s vibrant markets are also popular spots.

  • What are some hiking trails in Windsor and Maidenhead?

    Windsor Great Park has footpaths winding by woodlands and gardens, while the Thames Path offers scenic riverside walks. These trails welcome both relaxed and energetic hikers throughout the seasons.

  • What are some family activities we can do in Windsor and Maidenhead?

    Families often explore Windsor Castle, enjoy playtime at LEGOLAND Windsor Resort, and picnic along the Thames. Local parks and interactive museums make for engaging and relaxing days out.

  • What are some of the best day trip ideas from Windsor and Maidenhead?

    You can explore the historic market town of Marlow, stroll through Kew Gardens for botanical treasures, or discover Oxford’s famous university area for culture and architecture. Each destination has unique attractions and local flavors to enjoy.

  • Are there any pet friendly accommodations available in Windsor and Maidenhead?

    Windsor and Maidenhead has pet-friendly stays, especially in riverside neighborhoods and near public parks. Many hosts welcome pets, making it easy to explore local trails and green spaces with your companion.

  • What are some local tips for visiting Windsor and Maidenhead?

    Consider joining a guided walk by the Thames for local insights, and explore markets for regional flavors and artisan goods. Public transport connects many popular sites around town, and comfortable shoes help with cobbled streets and trails.

  • What is Windsor and Maidenhead known for?

    Windsor and Maidenhead is known for the iconic Windsor Castle, riverside views, and rich royal history. The area has vibrant markets, scenic parks, and cultural sites rooted in centuries of tradition.

  • What are the best hidden gems to explore in Windsor and Maidenhead?

    Explore Dorney Court, a Tudor manor with local history, or stroll Bray village’s quiet lanes known for charming pubs and gardens. The Alexandra Gardens are a peaceful spot for picnics along the Thames.

  • What are the best foods to try in Windsor and Maidenhead?

    Windsor and Maidenhead has classic British fare such as roasted meats, savory pies, and local cheeses. Neighborhood pubs and seasonal markets are frequently suggested for sampling regional cooking and fresh produce.

  • What should I bring for a trip to Windsor and Maidenhead?

    Bring comfortable walking shoes for cobbled streets and river paths, a rain jacket for occasional showers, and layers that suit year-round mild temperatures. A small daypack is useful for market visits or castle tours.

  • What is the nightlife in Windsor and Maidenhead like?

    Nightlife in Windsor and Maidenhead includes lively pubs, relaxed wine bars, and venues with live music and comedy. Riverside areas and Windsor’s historic streets host a mix of local favorites for evening hangouts.

  • What are the most popular events or festivals in Windsor and Maidenhead?

    The Royal Windsor Horse Show is often highlighted in spring, while Windsor Fringe Festival brings arts and performances in early autumn. Street fairs and food festivals around the river are popular community traditions.

  • Are there family friendly vacation rentals in Windsor and Maidenhead?

    Many vacation rentals in Windsor and Maidenhead welcome families, especially in central neighborhoods or near local parks. Look for properties with easy access to walking paths, playgrounds, and cultural sites for convenient outings.

  • When is the best time to visit Windsor and Maidenhead?

    Late spring through early autumn is frequently suggested for enjoying Windsor and Maidenhead, with warmer temperatures and outdoor festivals. Many visitors appreciate the area’s gardens and walks when flowers are in bloom.

Quick stats about holiday rentals in Windsor and Maidenhead

  • Total holiday rentals

    Explore 2,520 holiday rentals in Windsor and Maidenhead

  • Verified guest reviews

    Over 78,250 verified reviews to help you choose

  • Family-friendly holiday rentals

    1,220 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 530 rentals that welcome pets

  • Holiday rentals with a pool

    60 properties feature pools

  • Rentals with dedicated workspaces

    1,020 properties have a dedicated workspace

  • Wi-Fi availability

    2,430 of Windsor and Maidenhead holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Windsor and Maidenhead rentals

  • 4.7 Average rating

    Windsor and Maidenhead stays receive an average rating of 4.7 out of 5 from guests

  • Nearby attractions

    Windsor and Maidenhead's top spots, include Ascot Racecourse, Virginia Water Lake, and Odeon Maidenhead

Destinations to explore