Guesthouse holiday rentals in Windsor and Maidenhead
Find and book unique guesthouse rentals on Airbnb
Top-rated Guesthouses in Windsor and Maidenhead
Guests agree: These guesthouses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Windsor and Maidenhead guesthouses
Family-Friendly guesthouses
Guesthouse in Bennett End
4.87 out of 5 average rating, 406 reviewsMary's Cabin
Guesthouse in The Ayots
4.93 out of 5 average rating, 484 reviewsWhite Cottage Annexe with riverside garden hot tub
Guesthouse in North Stoke
4.98 out of 5 average rating, 170 reviewsStunning Lodge by Ridgeway/Thames
Guesthouse in Rudgwick
4.94 out of 5 average rating, 215 reviewsBucks Green Place Beautiful Converted Barn
Guesthouse in Thatcham
5.0 out of 5 average rating, 257 reviewsManstone Cottage, Yattendon
Guesthouse in Farnham
4.95 out of 5 average rating, 320 reviewsSelf Contained Garden Cottage
Guesthouse in Ashford
4.86 out of 5 average rating, 203 reviewsGarden cottage, easy for London & Surrey
Guesthouse in New Alresford
4.93 out of 5 average rating, 240 reviews17th century cottage Georgian town
Guesthouses with a patio
Guesthouse in Loudwater
4.96 out of 5 average rating, 108 reviewsWooden Garden Lodge
Guesthouse in Reading
4.96 out of 5 average rating, 114 reviewsPrivate Garden Annexe. Wheelchair accessible.
Guesthouse in Worminghall
4.91 out of 5 average rating, 108 reviewsCharming barn conversion with vast living space
Guesthouse in Lower Bourne
4.95 out of 5 average rating, 146 reviewsSelf contained studio in Lower Bourne, Farnham
Guesthouse in Hampshire
4.94 out of 5 average rating, 165 reviewsIMMACULATELY PRESENTED COUNTRY BARN FOR UP TO FOUR
Guesthouse in Oxfordshire
4.95 out of 5 average rating, 126 reviewsOxfordshire Country Cottage
Guesthouse in Wormley
4.89 out of 5 average rating, 109 reviewsAdorable one-bedroom hideaway with fantastic views
Guesthouse in London
4.84 out of 5 average rating, 172 reviewsThe Studio House - Crouch End
Guest house rentals with a washing machine and dryer
Guesthouse in Chalgrove
4.96 out of 5 average rating, 380 reviewsThe Post Office Barn Chalgrove
Guesthouse in Saint Albans
4.99 out of 5 average rating, 609 reviewsBed and breakfast .AL1.private quiet space.
Guesthouse in Brightwell-cum-Sotwell
4.99 out of 5 average rating, 137 reviewsA characterful, cosy, private annexe with parking.
Guesthouse in Chipstead
4.92 out of 5 average rating, 273 reviewsA private country escape with stunning views
Guesthouse in Harwell
4.92 out of 5 average rating, 159 reviewsHarwell, self contained cottage
Guesthouse in Dunsfold
4.95 out of 5 average rating, 217 reviewsThe Old Stable
Guesthouse in Hampshire
4.94 out of 5 average rating, 660 reviewsThe Old School House Liphook - hot tub & tennis ct
Guesthouse in Henley on Thames
4.89 out of 5 average rating, 391 reviewsDetached house sleeps 6, near Henley-on-Thames.
Quick stats about guesthouse rentals in Windsor and Maidenhead
Total rentals
70 properties
Popular amenities
Kitchen, Wi-Fi and Pool
Wi-Fi availability
70 properties include access to Wi-Fi
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Total number of reviews
4K reviews
Destinations to explore
- London Holiday rentals
- Central London Holiday rentals
- City of London Holiday rentals
- Oxford Holiday rentals
- Cotswold District Holiday rentals
- Cambridge Holiday rentals
- Bath Holiday rentals
- Bournemouth Holiday rentals
- Bristol Holiday rentals
- Birmingham Holiday rentals
- Nottingham Holiday rentals
- Cardiff Holiday rentals
- House rentals London
- Guesthouse rentals London
- Guesthouse rentals United Kingdom
- House rentals United Kingdom
- Guesthouse rentals England
- House rentals England
- Guesthouse rentals England
- House rentals England
- House rentals Berkshire
- Guesthouse rentals Berkshire
- Rentals with an EV charger Windsor and Maidenhead
- Rentals with a fireplace Windsor and Maidenhead
- Rentals with outdoor seating Windsor and Maidenhead
- Smoking-friendly rentals Windsor and Maidenhead
- Family-friendly rentals Windsor and Maidenhead
- Condo rentals Windsor and Maidenhead
- Wheelchair accessible rentals Windsor and Maidenhead
- Bed and breakfasts Windsor and Maidenhead
- Rentals with pools Windsor and Maidenhead
- Rentals with breakfast Windsor and Maidenhead
- Townhouse rentals Windsor and Maidenhead
- Rentals with a washing machine and dryer Windsor and Maidenhead
- Rentals with a patio Windsor and Maidenhead
- Fitness-friendly rentals Windsor and Maidenhead
- Cabin rentals Windsor and Maidenhead
- Pet-friendly rentals Windsor and Maidenhead
- Apartment rentals Windsor and Maidenhead
- Hotel rentals Windsor and Maidenhead
- Waterfront rentals Windsor and Maidenhead
- Rentals with a fire pit Windsor and Maidenhead
- Monthly Rentals Windsor and Maidenhead
- Kid-friendly rentals Windsor and Maidenhead
- Private suite rentals Windsor and Maidenhead
- Cottage rentals Windsor and Maidenhead
- House rentals Windsor and Maidenhead
- Rentals with a hot tub Windsor and Maidenhead
- Serviced apartment rentals Windsor and Maidenhead
- Rentals with lake access Windsor and Maidenhead
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom