Guest house holiday rentals in Windsor and Maidenhead

Find and book unique guest house rentals on Airbnb

Top-rated guest house rentals in Windsor and Maidenhead

Guests agree: these guest house rentals are highly rated for location, cleanliness and more.

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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.
Guest house in Berkshire
4.95 out of 5 average rating, 144 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!

Guest favourite
The open-plan living area features a contemporary kitchen with sleek cabinetry and modern appliances. A glass coffee table sits atop a colorful area rug in front of a cozy sofa. Natural light fills the space through two windows, accented by a vase of fresh tulips.
Guest house in Datchet
4.92 out of 5 average rating, 507 reviews

Luxury ♥️ 1 bed apartment Windsor Legoland Heathrow

Private self contained bungalow situated close to Windsor town centre. One-bedroom boutique style property plus a double pullout sofa bed, equipped with fully-fitted kitchen , lounge and bathroom with washing machine. Ideal for families visiting Legoland or historic Windsor, with excellent transport links, travel to central London takes just under an hour from Datchet station. Luxury features including a 'rain' shower, 400 thread count Egyptian cotton bedsheets Dolce gusto coffee machine

Top guest favourite
The exterior of the Brickmaker’s Loft displays a charming white facade with brown accents and multiple arched windows. A spiral staircase leads to the entrance, and a well-maintained garden is visible, featuring lush green grass and flower beds along the edge.
Guest house in Binfield
4.98 out of 5 average rating, 179 reviews

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.

Top guest favourite
The exterior of the lodge is showcased at night, highlighting warm lighting that illuminates the brick and wood paneling. Window shutters are closed, and a pathway leads to the entrance, accompanied by foliage and outdoor elements.
Guest house in Bracknell Forest
4.98 out of 5 average rating, 227 reviews

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

Guest favourite
A modern kitchen features light grey cabinetry with a farmhouse sink and stainless-steel appliances. A decorative backsplash with blue and beige tiles adds color. A small table and seating area are situated nearby, creating a functional and inviting cooking space.
Guest house in Pirbright
4.9 out of 5 average rating, 124 reviews

Lakehouse in Pirbright,Surrey

A peaceful private annex in a wonderful semi-rural location in the picturesque village of Pirbright. The annex has off street parking and its own separate entrance. Pirbright is an archetypal Surrey village, with a pretty village green and two excellent pubs. Surrounded by beautiful countryside it is perfect for walking and cycling. Brookwood mainline station is 2 miles away, providing a direct service to Waterloo. Guildford and Woking are close by providing theatres, bars and restaurants.

Guest favourite
A charming cottage is framed by a well-tended garden featuring a thatched roof. Comfortable seating is arranged on a grassy area, accompanied by a small table. The entrance door is flanked by windows adorned with flower pots, creating a welcoming look.
Guest house in Cookham Dean
4.85 out of 5 average rating, 103 reviews

Charming Cottage, dogs welcome, private garden .

A pretty cottage fully equipped for a comfortable holiday/ stay! Set back from the road, a peaceful haven. Private garden & parking. Easy walk to all local amenities & The River Thames. Great pubs &Michelin Star restaurants locally. The Chiltern Way offers a stunning path to all cyclists & walkers. Gorgeous old Towns of Windsor ( Legoland& Castle) Henley( Regatta & Festival)& Marlow (Tom Kerridge) , Cliveden, The Stanley Spencer Gallery,Train -London Paddington. M4 M40, Bicester Village .

Top guest favourite
A detached house with a brick and stucco exterior is visible. A paved driveway accommodates two vehicles, including a dark sedan and a blue SUV. Landscaping features a short hedge and a gravel area, framed by blue skies and a few scattered clouds.
Guest house in Berkshire
4.98 out of 5 average rating, 145 reviews

Self-contained studio Wokingham

A self-contained newly build 20 m2 studio with separate entrance and parking. The studio is comprised of an en-suite bathroom, a super-king bed, a tall boy and a work desk. A kitchenette just next to the room with fridge freezer, microwave, kettle, toaster, coffee machine, washing machine and a tumble dryer. “The kitchenette doesn’t have a stove or an oven.” The studio is brand new and built to high standards. The studio is a 15 minutes walk to Wokingham train station and town centre.

Guest favourite
A bright studio space features a spacious bed with crisp white linen, set against a backdrop of exposed wooden beams. A comfortable sofa is nearby, and sliding glass doors offer views of the garden, enhancing the feeling of openness and light.
Guest house in Cookham
4.89 out of 5 average rating, 548 reviews

Riverside Boathouse

A warm and cosy studio style converted boat house on the edge of the River Thames in Cookham, Berkshire. Separate from the main house, the double glazed studio boathouse with en-suite, decorated beautifully. Egyptian cotton linen and nice towels. Relax with views of the river. Blackout blinds, kitchen, en-suite shower room, fridge, double glazing, heating, TV, WIFI, laptop area, outdoor seating/picnic blanket, umbrellas, off road parking, boat mooring, EV Charging Point (fee applies).

Guest favourite
A spacious living area features high wooden ceilings and large windows allowing natural light. A comfortable sofa is positioned near a fireplace, with a cozy blanket placed atop. A rustic table and chair provide a workspace, while a soft rug adds warmth to the wooden floor.
Guest house in Taplow
4.95 out of 5 average rating, 516 reviews

Luxury Rustic Log Cabin... secluded deck & garden

A rustic cabin in lovely gardens adjacent to the main house. It has its own secluded garden & deck. Secure parking in large gravel drive. Ideal for Guests attending weddings/celebrations at Hedsor or Cliveden House Visiting the Gardens, Tea or Spa Day at Cliveden it’s on our doorstep! 8 miles to Windsor, visit a famous Castle. Beautiful walks by the River Thames, very pretty local villages with quaint country pubs Suitable two guests Please do NOT book if you are scared of dogs.

Top guest favourite
A light-filled living area features a gray sectional sofa with a patterned throw, a bright yellow bookshelf stocked with books, and a flat-screen TV mounted on the wall. Large windows allow natural light to illuminate the space, complemented by warm wooden flooring.
Guest house in Twyford
4.97 out of 5 average rating, 173 reviews

Spacious 2 Bedroom Cabin With Pool Table and Patio

The cabin is a fun and light filled space, perfect for families or couples. It boasts its own private patio, which leads to a secluded secret garden with an outdoor roll top bath! Inside there is a pool table and Sky TV. It is in the garden of a family home, situated half a mile from Twyford station, allowing easy access to Henley-on-Thames and London via the Elizabeth line. The cabin is accessed through a secure, key coded gate around the side of the main house.

Top guest favourite
A charming entrance features a neatly arranged bistro table and two chairs on a stone patio. Vibrant flowering pots in various colors add greenery, while a well-maintained lawn provides a welcoming ambiance. The brick exterior of the Annexe enhances the inviting appearance.
Guest house in Eversley
4.98 out of 5 average rating, 406 reviews

Modern One Bedroom Private Ground Floor Annexe

Our modern Annexe is located next door to our main home. It has its own private access and parking to the front. Ideally located for easy access to the M3 & M4 motorway network and close to Rivervale Barn, Warbrook House & The Elvetham wedding venues. There are three very good Pubs within walking distance, all do superb food. All local amenities are close by. Wellington Country Park and California Country Park are also within close driving distance.

Top guest favourite
A charming wooden barn is set amidst lush greenery and tall trees. A tranquil pond with water lilies reflects the surrounding foliage. Bright sunlight illuminates the scene, enhancing the peaceful outdoor space and the rustic charm of the barn.
Guest house in Buckinghamshire
4.98 out of 5 average rating, 257 reviews

The Barn at The Grove

The Barn is a self-contained recently converted space in the heart of the Chilterns. It is close to the riverside towns of Henley-on-Thames and Marlow and the surrounding Chiltern countryside. It is located on the edge of the village of Frieth with nearby farm shops and local gastro-pubs within a 5 min drive. The Barn is in a private and peaceful location with off-street parking. It is perfect for couples, solo travellers and small families.

Popular amenities for guest house rentals in Windsor and Maidenhead

When is the best time to visit Windsor and Maidenhead?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$121 SGD$136 SGD$149 SGD$153 SGD$165 SGD$189 SGD$152 SGD$158 SGD$162 SGD$144 SGD$148 SGD$153 SGD
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Quick stats about guest house rentals in Windsor and Maidenhead

  • Total holiday rentals

    Explore 80 holiday rentals in Windsor and Maidenhead

  • Nightly prices starting at

    Windsor and Maidenhead holiday rentals start at $78 SGD per night before taxes and fees

  • Verified guest reviews

    Over 5,120 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    80 of Windsor and Maidenhead holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Windsor and Maidenhead rentals

  • 4.8 Average rating

    Windsor and Maidenhead stays are highly rated by guests – averaging 4.8 out of 5!

  • Nearby attractions

    Windsor and Maidenhead’s top spots include Ascot Racecourse, Virginia Water Lake and Odeon Maidenhead

Destinations to explore