
Holiday houses in Old Windsor
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Quick stats about holiday rentals in Old Windsor

Total holiday rentals
Explore 60 holiday rentals in Old Windsor

Nightly prices starting at
Old Windsor holiday rentals start at $89 NZD per night before taxes and fees

Verified guest reviews
Over 2,720 verified reviews to help you choose

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

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
60 of Old Windsor holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Old Windsor rentals

4.7 Average rating
Old Windsor stays receive an average rating of 4.7 out of 5 from guests
Top-rated holiday rentals in Old Windsor
Guests agree: these stays are highly rated for location, cleanliness and more.

5* Boutique Hse Nr Windsor Castle, Ascot & London
This Grade 11 listed Mews property was built in 1872 and offers contemporary, luxurious living space. Luxurious king size beds, beautiful bathrooms, abundant art and character; the properties 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 all within 6 miles. Central London is 35 minutes by train. Heathrow is 6 miles away.

Cosy Cabin Retreat, 1–5 guests, 5 mins to Windsor
The Cosy Cabin is a peaceful retreat, ideal for couples or families up to 5. With two double bedrooms, a modern shower room, and comfortable open-plan lounge/kitchen/diner. Enjoy WiFi, Sky and Netflix, or explore nearby: Windsor Castle (5 mins), Legoland (10 mins), Thorpe Park (15 mins), Heathrow (20 minutes) and London under an hour by train. Perfect for romantic getaways and family breaks. Please note the access is through our utility room from a separate entrance into the garden to the cabin.

Gorgeous Self-Contained Wooden Cabin - Old Windsor
Beautiful and spacious self-contained log cabin comfortably sleeps 2-4. 1 king size bed, 1 small double sofa bed & 1 king size day bed (lounge). Shower/toilet, lounge and kitchenette. Close to Heathrow (7.4 miles / 15 mins) Great access to Windsor (2.4 miles). Close to a bus stop if needed. 2.5 miles to Runneymede where the Magna Carta was signed. Easy access to Ascot and Legoland The cabin is in the owner's garden. Friendly labrador included so please only book if comfortable around dogs!

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.

The Potting Shed
The Potting Shed, is a characterful & cosy self contained annex that can sleep 1-4 people. Benefiting from a private sheltered courtyard garden for dining or just a morning coffee. Ample off street parking on a gated drive. Overlooking horse fields, the property is close to Windsor Castle, Legoland, river walks, Windsor Great Park, Saville Gardens, Runnymede & easy access into London & Heathrow by train, bus or car. Within 40 mins to central London, Oxford or Warner Bros. Harry Potter world.

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.

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.

4-bed dog-friendly retreat w/ hot tub & garden
Welcome to a characterful four-bedroom home set within the historic Old Windsor Tapestries factory grounds. - Sleeps 9 | 4 bedrooms | 5 beds | 2.5 baths - Private hot tub (£150/stay) - open daily 8AM-9PM, all year round - Fenced backyard w/ BBQ, outdoor dining & communal garden access - Full kitchen w/ Bertozzoni double oven & dining table seats 10 - 48" HDTV w/ Netflix, fast wifi (73 Mbps) & dedicated workspace - Dog-friendly | free parking (x2) | keypad self check-in

River Thames near Windsor, Heathrow & London
Our home sits on the beautiful river Thames in Wraysbury near Windsor. The river runs past the end of the garden. There is a large west facing terrace, from the master bedroom. There is a large living room, kitchen and dinning room. 3 double bedrooms. There's parking for 2 cars in the garden. Windsor, Windsor castle and Lego land are about 20mins away my car. From Wraysbury station you can get into London Waterloo in 42mins. Heathrow is only 15mins drive away.

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

Windsor Great * Snug * Private Annexe with Parking
*stylish private annexe with off street parking for one car. * self contained studio attached to our family home. * suitable for up to 2 people only. * ideal for both work travellers (key box ) and tourists. * approx 21 m2 *quiet, leafy "Boltons" area. * 15\20 mins stroll to town centre and Castle. * 10 mins stroll to Long Walk and Great Park. * 5 mins cycle to Windsor Great Park cycle path. * local shop and pub 5-10 mins walk.

South Wing of Country House
Kick back and relax in this calm, stylish space. Only 35 mins by train from Central London, 8 miles from Heathrow. A small country estate with stunning gardens and 15 acres of land. Secure off street parking. Many tourist attractions in locality, plus easy access to UK motorways for trips further afield. Pool, Jacuzzi and sauna are for your sole use and available between 9a.m - 12 noon, and 4 - 7.00pm.
Popular amenities for Old Windsor holiday rentals
Other great holiday rentals in Old Windsor

The perfect stay in the heart of Windsor

The Royal Paddock

Racecourse Marina Lodge | Hot tub | Parking | EV

Calm spacious home w/ large terrace & free parking

Riverside Apartment Wraysbury, Nr Windsor/Heathrow

Royal Grand Cottage: Pond + Wildlife + Nature

Egham Retreat Contemporary | 2BR Peaceful Setting

Old Wharf Cottage
When is the best time to visit Old Windsor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $316 NZD | $367 NZD | $465 NZD | $392 NZD | $450 NZD | $530 NZD | $530 NZD | $525 NZD | $488 NZD | $470 NZD | $379 NZD | $477 NZD |
| Avg. temp | 6°C | 6°C | 8°C | 11°C | 14°C | 17°C | 19°C | 19°C | 16°C | 12°C | 8°C | 6°C |
Frequently Asked Questions
Are there family-friendly vacation rentals in Old Windsor?
Old Windsor has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Old Windsor?
Experience the best of Old Windsor with our house rentals, starting at about $50 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 Old Windsor?
Four-legged friends are welcome in Old Windsor. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Old Windsor?
Yes! Work meets play with ease at over 20 vacation rentals in Old Windsor featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Old Windsor have a kitchen?
Absolutely! We offer over 30 house rentals with a kitchen in Old Windsor. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Old Windsor have wifi?
Absolutely! We offer over 30 house rentals with wifi in Old Windsor. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Old Windsor have free parking?
Absolutely! We offer over 30 house rentals with free parking in Old Windsor. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Old Windsor?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with wifi, over 30 homes with free parking, over 30 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
Destinations to explore
- Wembley Stadium
- Covent Garden
- Kings Cross
- Paddington
- Hampstead Heath
- St Pancras International
- London Bridge
- ExCeL London
- The O2
- Brighton Seafront
- Emirates Stadium
- Tower Bridge
- West Wittering Beach
- Silverstone Circuit
- Clapham Common
- University of Oxford
- Goodwood Motor Circuit
- Buckingham Palace
- South Downs National Park
- Blenheim Palace
- Thorpe Park Resort
- Alexandra Palace
- Chessington World of Adventures Resort
- Big Ben





