
Guesthouse vacation rentals in Windsor and Maidenhead
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouse rentals in Windsor and Maidenhead
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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!

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

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

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.

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 .

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.

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).
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.

Self Contained Cottage in Thames Ditton Village
Beautiful self contained 1 bedroom cottage in the grounds of one of Thames Ditton’s oldest properties. Superbly located next to the river with pubs, restaurants, coffee shops, and village stores close by. Thames Ditton is a pretty village located close to Hampton Court, Surbiton, and Kingston Upon Thames and 30 minutes by train to London Waterloo. Go Boat hire is a minutes walk and the slipway to the Thames is opposite the house if you have your own paddle board/canoe.

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.

Modern Studio, Heathrow Prime Location.
Kick back and relax in this calm, stylish space. This is the perfect pit stop before travelling abroad or even the beginning of your staycation! Due to the popularity of our first listing we are proud to announce this newly renovated guest house, packed full of amazing amenities and unbeatable customer service! A stones throw away from all Heathrow Terminals with excellent travel links to Central London, this will be your home away from home.
Popular amenities for Windsor and Maidenhead guesthouse rentals
Family-friendly guest house rentals

The Cabin

Charming Private Guest House

Private Garden Annexe. Wheelchair accessible.

Luxury Garden Lodge

Detached studio within pretty walled garden.

A relaxing retreat close to the Thames.

Adorable studio log cabin in Buckinghamshire

Stunning One Bedroom Annex
Guest house rentals with a patio

Amazing Clockhouse in a perfect location

Cosy hideaway in the heart of Herts countryside

Self contained studio in Lower Bourne, Farnham

Large self-contained detached studio

Pump House, Open countryside with all the comforts

Acorns, in the picturesque village of Lower Froyle

Entire guest house studio - West Sussex

Peaceful & cosy detached annex with outdoor space
Guest house rentals with a washer and dryer

Stunning oak-framed "Loft House"

Bed and breakfast .AL1.private quiet space.

Beautiful garden cabin

The Post Office Barn Chalgrove

Beautiful Blossom Bothy(self contained)

The Old School House Liphook - hot tub & tennis ct

Bucks Green Place Beautiful Converted Barn

Charming 1 bedroom annex in a rural location
When is the best time to visit Windsor and Maidenhead?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R1,605 ZAR | R1,812 ZAR | R1,984 ZAR | R2,036 ZAR | R2,191 ZAR | R2,519 ZAR | R2,019 ZAR | R2,105 ZAR | R2,157 ZAR | R1,915 ZAR | R1,967 ZAR | R2,036 ZAR |
| 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 |
Quick stats about guesthouse rentals in Windsor and Maidenhead

Total vacation rentals
Explore 80 vacation rentals in Windsor and Maidenhead

Nightly prices starting at
Windsor and Maidenhead vacation rentals start at R1,035 ZAR per night before taxes and fees

Verified guest reviews
Over 5,120 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
80 of Windsor and Maidenhead vacation rentals include wi-fi 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
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- British Museum
- Covent Garden
- Buckingham Palace
- Big Ben
- Trafalgar Square
- Tower Bridge
- Wembley Stadium
- The O2
- London Bridge
- Hampstead Heath
- Emirates Stadium
- St. Paul's Cathedral
- St Pancras International
- ExCeL London
- Camden Market
- London Stadium
- Alexandra Palace
- Clapham Common
- Oxford University
- Blenheim Palace
- Goodwood Motor Circuit
- Primrose Hill
- Queen Elizabeth Olympic Park, London
- Windsor Castle