
Holiday houses in Winkfield Row
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Top-rated holiday rentals in Winkfield Row
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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.

Beautiful oak barn in peaceful countryside setting
Delightful detached barn crafted from French oak in a peaceful private lane on a gated country estate. Luxuriously appointed with full facilities for a short break or longer stay. Air Con. Free EV charging point. Many public footpaths close by. Local shops are only a 10 minutes stroll. Gastro pubs, restaurants and independent shops within easy walking distance. A short drive from M25 (J11). Fast rail links to London from Woking. LGBTQ+ friendly. Friendly Spaniel and Siamese cat on site.

The Brickmaker’s Loft
A newly fitted one bedroom apartment, with living area, full kitchen, large bedroom with king size bed, a full size single bed in the eaves, and an extra single bed if needed. We’ve kitted the Brickmaker’s Loft out with everything you would need. The kitchen has an oven, fridge, dishwasher, kettle, toaster, microwave and all the normal cooking bits, crockery etc. The bathroom has a walk-in shower, loo, and sink, and a washing machine if you need it. The bedroom is a lovely relaxing space.

Garden Lodge – Private Guest Suite in Bracknell
Detached guest lodge next to our family home in Bracknell. Lovely quiet location, just 0.7 miles from central Bracknell (The Lexicon). A modern bedroom with an ensuite shower room and a light refreshment area. Guests are welcome to enjoy full access to our family garden. 3 mins walk to Little Waitrose supermarket (open 24h), or KFC 5 mins walk to Harvester pub 7 mins walk to Leisure Centre (swimming pool, gym, spa, racket sports) 15 mins walk/5 mins drive to train station/central Bracknell

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.

Cosy private detached from main house large room
Private self-contained garden room with double bed, double sofa bed, WC and shower and separate dressing room. Access to quiet rear garden with seating. On-street parking on quiet residential side road. Kettle, microwave, airfryer, toaster, fridge. Wifi, Sky and Smart TV with Netflix. 1.7 miles to Ascot Racecourse, 2 miles to Ascot Station, 4.5 miles to Legoland, 7 miles to Windsor, 9 miles to Thorpe Park. A 5 minute drive to Lapland UK. Please message to discuss children’s discount.

Relaxing home near Legoland, Ascot, LaplandUK
This cosy cottage is situated in Windlesham, a pretty village in the Surrey Heath borough. Situated between Chobham Common and Swinley Forest, it is on the doorstep to some fantastic country walking and cycling routes; not to mention the famous golf courses in the area. Ideal location to visit Legoland, Thorpe Park, Ascot racing and Windsor castle. Heathrow Airport is only 15 miles away. Windlesham is known for the Boxing Day pram race and also a location to amazing gastro pubs.

2 Bedroom Luxury Cottage (Secure & Quiet)
This charming Cottage is located in the picturesque Village of Englefield Green. Just four miles from Windsor Castle, three miles from Wentworth Golf Course and six miles from Ascot Race Course. Heathrow Airport if just six miles away. 300 metres further down the lane is The Royal Air Force Memorial and below that, on National Trust grounds that skirts the River Thames is the Magna Carta Memorial. The Royal Holloway University is a ten minute stroll across the Village.

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

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.

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.

Robin’s Rest @ Scotlands House
Enjoy peaceful views of robins and deer across a field towards a stream. This unique space is peaceful and tranquil yet is also walking distance from the hustle and bustle of The Lexicon in Bracknell. Finished to an exceptional standard, Robin’s Rest @ Scotlands House offers luxury and tranquility, ideal for a weekend escape or longer stay.
Popular amenities for Winkfield Row holiday rentals
Other great holiday rentals in Winkfield Row

The Potting Shed - boutique countryside hideout

The Coach House

Ascot Spacious 2 bedroom flat Driveway Parking

Racecourse Marina Lodge | Hot tub | Parking | EV

Luxury House, Jennett's Park

Comfortable Courtyard Studio in Wokingham

Magnolia Lodge - 4 Beds, Fabulous Garden, Parking

Modern & Historic Duplex Flat Riverside
When is the best time to visit Winkfield Row?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $284 NZD | $262 NZD | $253 NZD | $236 NZD | $206 NZD | $406 NZD | $310 NZD | $317 NZD | $346 NZD | $343 NZD | $315 NZD | $308 NZD |
| Avg. temp | 5°C | 5°C | 7°C | 9°C | 13°C | 16°C | 18°C | 17°C | 15°C | 11°C | 8°C | 5°C |
Frequently Asked Questions
Are there family-friendly vacation rentals in Winkfield Row?
Winkfield Row has more than 60 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in condo rentals in Winkfield Row?
Experience the best of Winkfield Row with our condo rentals, starting at about $30 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 Winkfield Row?
Four-legged friends are welcome in Winkfield Row. Choose from more than 30 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Winkfield Row?
Yes! Work meets play with ease at over 50 vacation rentals in Winkfield Row featuring dedicated workspaces. Stay connected and productive in your home away from home.
Where should I stay in Winkfield Row?
Make yourself at home in Winkfield Row by choosing from our most frequently booked neighborhoods. We have over 350 vacation rentals in Ascot, over 250 vacation rentals in Harmans Water, and over 400 vacation rentals in Winkfield Row.
Do condo rentals in Winkfield Row have a kitchen?
Absolutely! We offer over 10 condo rentals with a kitchen in Winkfield Row. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Winkfield Row have wifi?
Absolutely! We offer over 60 house rentals with wifi in Winkfield Row. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Winkfield Row have free parking?
Absolutely! We offer over 60 house rentals with free parking in Winkfield Row. Enjoy a tailored experience with all the comforts you desire.
Quick stats about holiday rentals in Winkfield Row

Total holiday rentals
Explore 120 holiday rentals in Winkfield Row

Nightly prices starting at
Winkfield Row holiday rentals start at $51 NZD per night before taxes and fees

Verified guest reviews
Over 3,410 verified reviews to help you choose

Family-friendly holiday rentals
60 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
110 of Winkfield Row holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Winkfield Row rentals

4.8 Average rating
Winkfield Row stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Apartment rentals Winkfield Row
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- Pet-friendly rentals Winkfield Row
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- Family-friendly rentals Winkfield Row
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- South Downs National Park
- Paddington
- Covent Garden
- British Museum
- St Pancras International
- Hampstead Heath
- Buckingham Palace
- The O2
- Wembley Stadium
- Tottenham Court Road
- Tower Bridge
- Marble Arch
- London Bridge
- Big Ben
- Natural History Museum
- Trafalgar Square
- ExCeL London
- Emirates Stadium
- Battersea Power Station (disused)
- Royal Albert Hall
- Russell Square
- Olympia Events
- Borough Market
- Clapham Common





