Vacation rentals in Oakley Green

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Top-rated vacation rentals in Oakley Green

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

An open-plan kitchen and living area features a wooden countertop with bar seating. The room is illuminated by natural light from the skylight, highlighting the contrasting blue and white walls. A cozy sofa and decorative artwork create a welcoming space.

Guesthouse in Windsor

4.94 out of 5 average rating, 202 reviews

Windsor Home with Free Parking

Welcome to our 1-bedroom, skylit, guest house with off-road parking & private patio. Located in a quiet cul-de-sac close to Legoland, Windsor Racecourse, and Windsor Castle, our home is the perfect retreat after a long day of sightseeing. The bedroom can be set up with either a kingsize bed or 2 singles on request, while the sofa bed can comfortably fit 2 people. Our family run Airbnb is a great fit for families with kids, a couple or a small group of friends. Any questions, please just ask!

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Top guest favorite

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 Old Windsor

4.99 out of 5 average rating, 109 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.

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Top 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

4.95 out of 5 average rating, 165 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

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Guest favorite

A bright and inviting sleeping area is showcased, featuring a king-size bed with soft linens and decorative pillows. A striking artwork of a colorful bull is displayed above the bed, while a cozy blue sofa rests in the foreground against warm wooden walls.

Cottage in Bray

4.98 out of 5 average rating, 114 reviews

Studio East & Petting Farm, Near Legoland-Lapland

Studio East is a very cool, self contained, detached, self catering, open plan studio with private secure parking, large private fenced garden, free superfast WIFI with a 50 inch cable TV. There is also a small on site petting farm! Studio East has a king size bed along with bespoke bunk beds that the kids will just love and has a maximum occupancy of 2 adults and 2 children. Located in Oakley Green on the edge of Windsor and only 10 minutes from Windsor town centre, Lapland Uk and Legoland.

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Guest favorite

A rustic barn-style exterior features a mix of brick and timber. The building is complemented by a wooden deck with several white metal chairs arranged around a table, surrounded by greenery and a wooden fence. Two dormer windows are visible on the roof.

Condo in Buckinghamshire

4.93 out of 5 average rating, 227 reviews

Gardener's Bothy loft apartment, peaceful location

Loft apartment, newly refurbished in 2020, in converted barn in unique rural location. Minutes walk from the Thames towpath and convenient for events at Dorney Rowing lake. 10 minutes drive to the M4, close to Windsor town centre and handy for Slough Trading Estate, difficult to believe this is all so close to this unique and peaceful location overlooking fields and Dorney Common. Lovely place for walkers and great base for many local attractions. Ideal spot to work or just relax.

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Top guest favorite

The living room features a leather sofa paired with a stylish chair, both positioned around a wooden coffee table. Large glass doors open to the private garden, while a flat-screen TV is mounted on a wooden accent wall, providing a cozy and modern atmosphere.

Guest suite in Bray

4.96 out of 5 average rating, 25 reviews

Private Annex & garden, near Windsor & Bray

A beautiful, modern ground floor private annexe and garden. Fully self contained with private entrance and secure parking. Living room/ diner leading on to private garden area. Separate toilet. Kitchen with hob and built in oven with extractor fan. Microwave, kettle, toaster and fridge. Washing machine and tumble dryer. All crockery & cutlery provided. Double bedroom with king size bed and en-suite shower & toilet. Large Flat screen TV's in bedroom & lounge. Separate toilet.

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Top guest favorite

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 Bracknell Forest

4.97 out of 5 average rating, 363 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

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Guest favorite

A modern lodge is surrounded by a glass balustrade, offering a clear view of the outdoor terrace furnished with a dining table and chairs. The well-maintained lawn provides a vibrant green space, and large windows reflect the bright sky with scattered clouds.

Home in Windsor

4.97 out of 5 average rating, 79 reviews

Racecourse Marina Lodge | Hot tub | Parking | EV

Live your high life on Windsor Racecourse Marina! Discover your dream get away with this beautifully designed luxury lodge located in a prestigious gated community. This property is perfect for a couple or a family looking to enjoy a relaxing luxurious lifestyle in tranquillity and peace. With amazing views over Windsor Racecourse and the boats moored on the marina, every moment here is a picture of calm elegance.

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Guest favorite

Condo in Windsor

4.94 out of 5 average rating, 201 reviews

Modern Windsor home with free off-street parking

Welcome to our stylish, child-friendly 2-bed apartment in central Windsor! Ideal for families, couples, or a business stay. Just a short walk to Windsor Castle, shops and the train station. Legoland and Lapland UK are also closeby, plus there's easy access to London and Heathrow. Enjoy free parking, fast Wi-Fi, a fully equipped kitchen, and a spacious living area—perfect for relaxing after a day out.

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Superhost

The spacious living area features high wooden beams and large windows that allow ample natural light. A fireplace is centrally located, framed by a mix of comfortable seating and a glass coffee table. A staircase leads to the upper level, enhancing the open design.

Barn in Buckinghamshire

4.92 out of 5 average rating, 113 reviews

Dorney/Windsor Family Getaway with Hot Tub

Unwind with your entire family in our breath-taking barn, brimming with personality and allure. Nestled in a tranquil rural village, it offers access to two charming pubs and a plethora of picturesque countryside and river trails. Just a short drive away, the renowned destinations of Windsor and Eton await, inviting you to immerse yourself in their famed landmarks and rich historical architecture.

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Top guest favorite

Home in Bray

5.0 out of 5 average rating, 13 reviews

The Den

Experience comfort and convenience in our studio en-suite, Free on-street parking included. Located just 10 minutes from Maidenhead & 12 minutes from Windsor train stations. The bus stop is a short stroll away, making public transport accessible. For everyday essentials, a 24-hour BP petrol station with a fully stocked shop is just a 3-minute drive away.

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Superhost

Home in Bray

4.73 out of 5 average rating, 11 reviews

Rural 2 bedroom Lodge In Windsor with Hot Tub!

Relax with the whole Welcome to your perfect countryside escape, just moments from Windsor. Whether you’re planning a relaxing break with family and friends or need a comfortable base for work, this home offers the best of both worlds — tranquillity and convenience. family at this peaceful place to stay.

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