Vacation rentals in Windsor and Maidenhead

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Top-rated vacation rentals in Windsor and Maidenhead

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Top guest favorite
A cozy bedroom is depicted with a double bed featuring decorative pillows. The walls are adorned with various framed artworks and photographs, contributing to a personalized aesthetic. A small nightstand is visible beside the bed, and an open door leads to a well-lit hallway.
Guest suite in Egham
4.93 out of 5 average rating, 207 reviews

Self-contained Annex Studio Flat

The accommodation consists of a double bedroom with French doors opening onto a nice big garden. There is a fully fitted kitchen and a small bathroom with walk-in shower. Broadband, TV, fridge, washing machine and drier are all included. It is about 50 yards from Egham station which has regular trains to London, the journey taking about 40 minutes. The train goes to Waterloo Station which is very close to the London Eye and Westminster, with Buckingham Palace, St James Park, Trafalgar Square a short walk away. Heathrow Airport is 5 or 6 miles away. Egham is a small town, but it has some historic interest in that the Magna Carta was signed at Runnymede down the road by the river in 1215. Not far away is Windsor castle and Eton (where princes William and Harry, and David Cameron went to school). There is also some lovely countryside around and lovely walks.

Top guest favorite
A marching band of guards in red uniforms and tall black hats moves down a street lined with historic buildings. The scene captures the vibrant atmosphere of Windsor, as onlookers watch from above, framed by the charming architecture.
Condo in Berkshire
4.99 out of 5 average rating, 132 reviews

Spacious & light 2bd, 2ba in the heart of Windsor

This beautiful 2bed, 2bath apartment, with parking, in the heart of Windsor, is an exceptional find. With Windsor Castle (watch the marching bands for the Changing of the Guard pass right outside your front door!), Windsor Great Park, The Guildhall, beautiful Eton and its own historic town centre with fabulous shops, restaurants, bars and clubs all only minutes away on foot, you couldn't be better placed for your stay. Windsor is also a very short drive from both Ascot Racecourse and Legoland.

Superhost
An open-plan living space features a wooden ceiling beam, creating a cozy ambiance. The kitchen is equipped with modern appliances, and a comfortable seating area is arranged with stylish chairs and a sofa, with natural light flowing in through the large windows.
Cottage in Winkfield Row
4.91 out of 5 average rating, 227 reviews

Unique Cottage, Beautiful Views, Ascot, Windsor

This is the perfect hideaway to retreat, unwind and escape from the pressures of life. The cottage is a newly refurbished, converted stable block, set in a unique location. Close to historic towns & villages including Ascot and Windsor with direct trains from London Waterloo and close to the M4, M25 & M3. A plethora of Michelin starred restaurants, wonderful walks in Windsor Great Park, Virginia Water & the neighbouring Chilterns await you! Ideally situated for visiting Lapland UK and Legoland.

Guest favorite
A charming exterior of the converted barn is framed by lush greenery, featuring a wooden deck and double doors. A cozy outdoor seating area with wicker chairs and a table is surrounded by an assortment of potted plants and flowers, enhancing the tranquil garden setting.
Barn in Warfield
4.91 out of 5 average rating, 839 reviews

Delightful small converted barn

Unique newly converted small barn, bright, light and self contained. Sleeps 3 adults or 2 adults and 2 children (or 2 small adults) due to restricted height space in loft. Large gravel drive behind big, wooden gates for safe and easy parking. An assortment of Teas, coffee & biscuits. Breakfast is not provided. Situated down a country lane, within the garden of the house, walking distance to pubs and restaurants. Near Lapland UK, Legoland, Ascot, Windsor, Train stations to London and Reading

Top guest favorite
A riverside log cabin is nestled among trees, featuring a spacious deck and seating area overlooking the water. Lush greenery surrounds the outdoor space, creating a natural setting that invites relaxation. The cabin’s wooden structure blends harmoniously with its peaceful environment.
Cabin in Reading
4.98 out of 5 average rating, 420 reviews

Riverside Log Cabin+Luxury Hot Tub Spa+Copper bath

Charming, riverside log cabin on the bank of the Kennett, overlooking a nature reserve. Privately located in my back garden there is a large open plan room with 2 double sofa beds, sleeping 4, a slate bed pool table & Hi Fi system. There's a luxury en suite bathroom with copper bathtub, shower, basin & WC. There are basic kitchen facilities with kettle, toaster, double hot plate, microwave & grill, sink & refrigerator/freezer. A veranda with 2 bbq's & seats plus lower deck overlook the river.

Guest favorite
A bright living area features two large sofas in green tones and a stylish glass coffee table. A dining table with four chairs is set for a meal, complemented by wall art and natural light from a window with curtains.
Apartment in Berkshire
4.95 out of 5 average rating, 170 reviews

Apartment in Windsor

Newly refurbished apartment located 10 minutes walk from Windsor Castle and the town centre with all of its great shops, bars, restaurants and tourist attractions. Benefits from its own private entrance, double bedroom, wet room, kitchen and separate living room with 2 large sofas and dining area. Easy access to the M4 and only a 10 minute walk to the train station with direct links into London, it is ideally located for a business stay or as a base to explore Windsor and the surrounding area.

Top guest favorite
The entrance to the Garden View Suite is framed by vibrant flower boxes on either side. A clear glass door, with a welcoming sign, invites guests into the private space. A small gate leads to a lush garden area filled with greenery.
Guest suite in Old Windsor
4.97 out of 5 average rating, 298 reviews

Garden View Annex Private Free parking River walks

Take a gentle walk from here along the Thames Path to historic National Trust Runnymede, with its tea shop, many monuments to Magna Carta and beautiful outdoor art works. Less than 2 miles from The Long Walk, explore Windsor and the Castle or visit Saville Garden in the Great Park. We're also close to Legoland. Old Windsor has lots of places to eat (see guidebook) all in walking distance, we're surrounded by beautiful walks and we're also on the direct bus route to Windsor and Heathrow.

Guest favorite
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
4.93 out of 5 average rating, 119 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

Guest favorite
A charming cottage is framed by a well-tended garden featuring a thatched roof. Comfortable seating is arranged on a grassy area, accompanied by a small table. The entrance door is flanked by windows adorned with flower pots, creating a welcoming look.
Guesthouse in Cookham Dean
4.85 out of 5 average rating, 103 reviews

Charming Cottage, dogs welcome, private garden .

A pretty cottage fully equipped for a comfortable holiday/ stay! Set back from the road, a peaceful haven. Private garden & parking. Easy walk to all local amenities & The River Thames. Great pubs &Michelin Star restaurants locally. The Chiltern Way offers a stunning path to all cyclists & walkers. Gorgeous old Towns of Windsor ( Legoland& Castle) Henley( Regatta & Festival)& Marlow (Tom Kerridge) , Cliveden, The Stanley Spencer Gallery,Train -London Paddington. M4 M40, Bicester Village .

Guest favorite
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, 438 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

Guest favorite
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 favorite
The entrance to the house features a covered porch framed by lush greenery and climbing plants. A pathway leads to the front door, which opens into a welcoming lobby. Stacked logs are visible beside the entrance, adding a rustic touch to the outdoor space.
Condo in Berkshire
4.97 out of 5 average rating, 193 reviews

Cheerful modern apt central Maidenhead, parking

Quiet location with free driveway parking, excellent road/rail links to London. On a tree lined street, 7 minutes walk from the Town Centre and Railway Station (London or Oxford 1hr max) The private space includes 2 double bedrooms, a large bathroom, en-suite shower room, a well equipped kitchenette and a relaxing lounge area Maidenhead Town Centre is being transformed with new restaurants, bars, coffee shops, and a new Leisure Centre 20 mins walk

Popular amenities for Windsor and Maidenhead vacation rentals

When is the best time to visit Windsor and Maidenhead?

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Avg. priceR2,276 ZARR2,189 ZARR2,241 ZARR2,450 ZARR2,606 ZARR2,902 ZARR2,971 ZARR2,919 ZARR2,728 ZARR2,485 ZARR2,415 ZARR2,519 ZAR
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Frequently Asked Questions

  • Where should I stay in Windsor and Maidenhead?

    Make yourself at home in Windsor and Maidenhead by choosing from our most frequently booked neighborhoods. We have over 150 vacation rentals in Touchen-End, over 1,060 vacation rentals in Eton Wick, and over 180 vacation rentals in Britwell.

  • Are there Windsor and Maidenhead vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 60 vacation homes with pools in Windsor and Maidenhead, available on Airbnb. Make a splash and soak up the sun in style!

  • Do bed and breakfast rentals in Windsor and Maidenhead have wifi?

    Absolutely! We offer over 20 bed and breakfast rentals with wifi in Windsor and Maidenhead. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Condo Rentals in Windsor and Maidenhead?

    Enhance your stay in our Condo Rentals with the most popular amenities: over 180 homes with wifi, over 180 homes with a kitchen, over 130 homes with free parking, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Windsor and Maidenhead have free parking?

    Absolutely! We offer over 870 house rentals with free parking in Windsor and Maidenhead. Enjoy a tailored experience with all the comforts you desire.

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

    Windsor and Maidenhead has more than 1,220 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in serviced apartment rentals in Windsor and Maidenhead?

    Experience the best of Windsor and Maidenhead with our serviced apartment rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Windsor and Maidenhead?

    Four-legged friends are welcome in Windsor and Maidenhead. Choose from more than 530 vacation rentals for guests traveling with pets.

  • Do apartment rentals in Windsor and Maidenhead have air conditioning?

    Absolutely! We offer over 30 apartment rentals with air conditioning in Windsor and Maidenhead. Enjoy a tailored experience with all the comforts you desire.

  • Do guesthouse rentals in Windsor and Maidenhead have a kitchen?

    Absolutely! We offer over 50 guesthouse rentals with a kitchen in Windsor and Maidenhead. Enjoy a tailored experience with all the comforts you desire.

Quick stats about vacation rentals in Windsor and Maidenhead

  • Total vacation rentals

    Explore 2,520 vacation rentals in Windsor and Maidenhead

  • Verified guest reviews

    Over 78,250 verified reviews to help you choose

  • Family-friendly vacation rentals

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

  • Pet-friendly vacation rentals

    Find 530 rentals that welcome pets

  • Vacation 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 vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, 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