
Pet-friendly holiday rentals in Old Windsor
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Top-rated pet-friendly home rentals in Old Windsor
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Stunning 3-bedroom castle view Windsor townhouse
Enjoy a stylish experience at this centrally-located 3 storey Georgian townhouse. Recently refurbished to a high standard with a modern twist. This deceptively spacious 3-double bedroom house is spread over 3 floors. It comes with the bonus of Off Street, Private, Secure PARKING and a view of the castle (in winter!) and a patio. It is adjacent to a small park with a childrens' play area and relaxing shaded seating. It's a unique accommodation appointed to make your break special and memorable.

Luxury Shepherd's Hut with stunning sunset views!
Welcome to Honeysuckle, our luxury shepherd's hut with stunning views across the fields in the Chilterns. In the evenings sit and watch the sun go down around your fire pit or stay cosy indoors with your log burner. We are a working farm and you may see the tractor trundle past feeding our herds of Texal sheep (Lambing right in front of you in March/April 2025!) and Limousin cows grazing in fields, or watch the many birds. You have your own secluded, fenced and private garden area with seating.

Ground floor studio with private entrance
A quiet, ground floor studio flat, fully self-contained, affording high levels of privacy & comfort, with freedom to come & go via your own front door at anytime day or night. Situated in a quiet, safe, leafy cul-de-sac in Cobham (dubbed UK’s Beverly Hills!) which offers: The Ivy, gastro pubs, boutique shops, Waitrose & more. Driving: 5mins to Oxshott station, 10mins to M25, 20mins to Guildford (or train). Airports: Heathrow (10miles), Gatwick (16miles). Trains to London Waterloo: 35mins.

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.

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

The Old Barn , Organic Residence, outside seating
2 x king size organic bedroom-en-suites, with off street parking, great base for work or vacation, my Italian cousin Angelo, calls it " Tuscany in the Chilterns " home to "Midsummer Murders" ,"Wind in the Willows" and Agatha Christie's, "Miss Marple & Poirot mysteries", 200 year old country barn two fields from the Thames, beautiful views, and one of a few areas in the UK where you have hills and valleys and a navigable river wrapping around them, encircled by picturesque riverside towns

Royal Windsor Castle 5 min lux 2 Bed 2bath+Garden
Welcome to Central Windsor. Only a 10 -15 min walk to Windsor Castle - The long walk / Great Park -Local shops -Restaurants Cafes -Pubs -Arts centre -Theatre •Good transport links to London - Heathrow 20 minutes by taxi -702/703 buses to bottom of Grove road . Super comfy king size bed with en-suite wet room plenty of wardrobe space Small double bedroom & second bathroom (extra nightly charge p) Kitchenette Microwave Washing machine . Private Patio No smoking/ Vaping please.

Gardeners’ Cottage (Georgian stable conversion)
An entirely self contained cottage, recently converted from a Georgian stable and gardeners’ lodge. While adjacent to the owners property it is entirely separate, with its own secure parking and EV charger. Located in a small village, with two pubs on doorstep. Market town of Wallingford (setting for “Midsomer Murders”) is short walk, many amenities including boat rides on the River Thames an outdoor heated pool (summer), great restaurants and shops including Waitrose.

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.

Quirky 1 Bed split level Apartment Free parking
Quirky 1 Bedroom Apartment set over two floors, Quality brand new kitchen, Spacious yet cozy with all mod cons and easy access to London via Waterloo train station 1 min walk away. Regular buses (No 8 ) & (442) to Heathrow. Also covered free parking for 1 car right outside the door. A two minute walk to Waitrose and high street where you'll find shops bars and restaurants and cinema. Key safe code easy checkin and meet and greet. Corporate bookings welcome.

Luxury Boathouse Apartment - central Henley
The Boathouse is a completely private studio apartment with wonderful river views. Furnished to a high standard with luxury bed linens and towels, and fully equipped with everything you could need. The perfect location for the Henley Royal Regatta, Henley Festival and The Rewind Festival Relaxing location that is perfect for watching the world and river go by, but also close enough to the hustle and bustle of the town and it's many restaurants and cafes.

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.
Popular amenities for Old Windsor pet-friendly home rentals
Pet-friendly house rentals

Beautiful 3 bed home with large driveway parking

Gorgeous Cottage in Skirmett with Parking

Charming Goring house – riverside walks & pubs

The Neptune

18th century cottage

Magical Marlow town centre

Film Studio*Heathrow Airport*Families*Long Stays

The Stables, Little Marlow
Pet-friendly home rentals with a pool

Ancient barn with private heated pool and hot tub

Luxury Battersea studio w open fire, close to Park

An amazing flat in Chelsea!

Bell Tent Glamping Single unit, self contained.

4 bedroom Lodge/Hotub-Pool in Surrey UK

The Barn at Holly Cottage. Indoor Pool and tennis

Romantic Swedish cabin in magical setting

One bedroom apartment Mickleham, near Dorking
Private, pet-friendly home rentals

Charming Stylish Cottage at Windsor Great Park

Luxury Gatehouse in Rural Location

Penthouse in Putney.

Serene & Private Annexe in Village Centre

Beautiful 4bd home w/ hot tub & parking

Hampton Court Grand Snug Sleeps 2-6 Walk to Palace

The River Nest

The Snug - adorable, private, 1-King bed cottage.
Quick stats about holiday rentals that are pet-friendly in Old Windsor

Total holiday rentals
Explore 20 holiday rentals in Old Windsor

Nightly prices starting at
Old Windsor holiday rentals start at £82 per night before taxes and fees

Verified guest reviews
Over 770 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Wifi availability
10 of Old Windsor holiday rentals include wifi access

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

4.6 Average rating
Old Windsor stays receive an average rating of 4.6 out of 5 from guests
Destinations to explore
- South Downs National Park
- Tower Bridge
- Paddington
- Big Ben
- British Museum
- Covent Garden
- London Bridge
- Hampstead Heath
- St Pancras International
- Marble Arch
- Buckingham Palace
- Wembley Stadium
- Kings Cross
- Tottenham Court Road
- The O2
- Natural History Museum
- Trafalgar Square
- Piccadilly Theatre
- ExCeL London
- Battersea Power Station (disused)
- Emirates Stadium
- Royal Albert Hall
- Russell Square
- Olympia Events




