Holiday houses in Oakley Green

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Top-rated holiday rentals in Oakley Green

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

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Top Guest favourite
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!

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 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.

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
4.95 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

Top Guest favourite
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, 461 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 favourite
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.

Guest favourite
The exterior of a charming stone barn is illuminated at night, highlighting its rustic architecture. Soft lighting from below enhances the textures of the stone walls and draws attention to the barn doors. A sculptural feature is visible in the foreground, adding interest to the serene landscape.
Barn in Great Milton
4.95 out of 5 average rating, 242 reviews

17th Century Barn in quiet country village

A 17th Century Hay Barn 7 miles from Oxford and in the same village as ‘Le Manoir aux Quat’ Saisons’. Enjoy a glass of bubbles on your own private terrace before strolling to dinner at this famous Cotswold stone Manor. Fully wheelchair accessible & with private parking this unique property is the perfect place for a few days away walking in the nearby Chilterns, exploring Oxford’s Colleges & Cafes, visiting Art & Literary Fairs or attending appointments at Oxford’s many leading hospitals.

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 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

Guest favourite
A couple relaxes in a bubbling outdoor hot tub, holding glasses, with a scenic view of lush green fields and trees in the background. A champagne bottle sits in an ice bucket beside them, enhancing the tranquil atmosphere.
Shepherd’s hut in Chessington
4.98 out of 5 average rating, 375 reviews

The Ultimate Couples Retreat | 30 Mins from London

This countryside retreat is the perfect romantic escape, just a 35 minute taxi/train ride minutes from London. Unwind in your private luxury hot tub, sip on a complimentary bottle Champagne under the stars, and wake up to breathtaking views of rolling fields and wildlife. Our handcrafted shepherd’s hut blends rustic charm with modern comfort, offering a king-sized stargazing bed, a cozy fire-lit deck, and a luxury bathroom, all set in a peaceful meadow.

Guest favourite
An aerial view showcases the unique geo dome structure surrounded by lush greenery. A wooden deck leads to an outdoor seating area, fire pit, and hot tub. The tranquil setting emphasizes a peaceful retreat in nature.
Dome in West Horsley
4.94 out of 5 average rating, 407 reviews

Unique Dome | Glamping | Hot Tub | Surrey | Adults

Olive Pod is the ultimate cosy, private and picturesque geo dome retreat. Set on a fruit farm in Surrey, in its own secluded field behind tall fir trees, with no other pods or tents nearby. A firm favourite adults-only escape for proposals, anniversaries, birthdays and honeymoons - we can also decorate for your arrival ✨ The perfect place to unwind and recharge in a peaceful natural setting. Ideal for couples or friends. No infants, children or pets.

Top Guest favourite
A charming self-contained cottage is set within a lush private garden, characterized by brick exterior and a slate roof. A welcoming door leads to the entrance, framed by greenery and flowering plants, with a spacious lawn surrounding the building.
Cottage in Sunninghill
4.96 out of 5 average rating, 876 reviews

The Old School House, Ascot, Berkshire

Beautiful small self-contained character cottage set within private garden, one mile from Ascot. Open plan studio room with sitting area, kitchenette and bedroom area; en suite shower room/WC. Perfect for 1-2 adult guests looking for a comfortable and relaxing place to stay, whether for business or pleasure. It is ideal for visitors to Ascot Races, Windsor, close to Heathrow and a lovely rural retreat less than one hour from central London.

Superhost
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.

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.

Popular amenities for Oakley Green holiday rentals