Pet-friendly holiday rentals in Old Windsor

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Top-rated pet-friendly home rentals in Old Windsor

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Guest favourite
The exterior of a Georgian townhouse is depicted, featuring a mix of white and brown brick facades. Bright red doors enhance the building's character, while multiple square windows provide natural light. A low iron railing suggests a welcoming approach to the entrance.
Townhouse
4.81 out of 5 average rating, 227 reviews

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.

Top guest favourite
A welcoming entrance is framed by a rustic wooden gate and lush greenery. The shepherd's hut is visible in the background, with a soft sunset illuminating the sky and reflecting off the structure. Pathways bordered by wildflowers lead towards the fields beyond.
Shepherd’s hut
4.99 out of 5 average rating, 621 reviews

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.

Top guest favourite
The spacious bed is dressed in white linens, complemented by decorative pillows featuring tropical patterns. Gold sconces flank the bed, illuminating the unique textural wall with intricate patterns. A round mirror adds depth, reflecting the soft lighting in the cozy sleeping area.
Guest house
4.96 out of 5 average rating, 311 reviews

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.

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
4.99 out of 5 average rating, 102 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
4.94 out of 5 average rating, 139 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

Superhost
A charming exterior of a two-story barn is nestled among greenery and flowering plants. The roof features wooden shingles, and the upper windows allow natural light to flood in, showcasing a serene landscape of rolling hills and fields in the background.
Home
4.88 out of 5 average rating, 214 reviews

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

Guest favourite
A serene bedroom features a spacious bed adorned with neutral linens and decorative pillows. Soft, warm lighting is provided by two hanging lamps, while artwork decorates the walls. Fresh towels are neatly arranged on a textured blanket at the foot of the bed, alongside a woven basket.
Apartment
4.92 out of 5 average rating, 142 reviews

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.

Top guest favourite
A charming exterior of a converted stable features a combination of dark wooden panels and warm brickwork. Large windows with grid patterns invite natural light, while the entrance is highlighted by a rustic door. A gravel path leads up to the front, framed by greenery.
Cottage
4.96 out of 5 average rating, 391 reviews

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.

Guest favourite
A spacious terrace is furnished with wicker seating and a wooden table, providing a comfortable area for relaxation. The serene view of the river Thames is framed by lush greenery and a bright blue sky, creating a peaceful outdoor setting.
Home
4.97 out of 5 average rating, 143 reviews

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.

Superhost
A sleeping area features a spacious bed with a white textured duvet and decorative pillows. Two bedside tables are positioned on either side of the bed, beside lamps. Towels are neatly arranged on the foot of the bed. Soft natural light brightens the room.
Flat
4.71 out of 5 average rating, 126 reviews

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.

Top guest favourite
A contemporary studio apartment is positioned along the riverbank, featuring a modern design with large glass windows. A graceful weeping willow tree frames the scene, adding a natural element to the tranquil waterfront setting. Gentle ripples are visible on the water's surface.
Loft
4.94 out of 5 average rating, 211 reviews

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.

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
4.98 out of 5 average rating, 346 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.

Popular amenities for Old Windsor pet-friendly home rentals

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