
Guesthouse vacation rentals in Windsor and Maidenhead
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Top-rated guesthouse rentals in Windsor and Maidenhead
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Windsor and Maidenhead guesthouse rentals
Family-friendly guest house rentals

The Cabin

Entire Cabin. Kingston/ Wimbledon/ Waterloo.

A private country escape with stunning views

Adorable 1 bedroom guest house in Chobham

Self contained studio in Lower Bourne, Farnham

Cosy Cabin Virginia Water/Longcross

Cosy detached studio- walking distance to CWOA!

The Chalet at Rosemary Cottage
Guest house rentals with a patio

Adorable one-bedroom hideaway with fantastic views

The Studio House - Crouch End

Stunning oak-framed "Loft House"

Garden Studio in the heart of Highgate Village

Private Garden Annexe. Wheelchair accessible.

Large self-contained detached studio

Charming 1 bedroom annex in a rural location

Acorns, in the picturesque village of Lower Froyle
Guest house rentals with a washer and dryer

Spacious annexe ~ two bedrooms, rural, EV charger

Spacious private ensuite, superb views near Oxford

Bed and breakfast .AL1.private quiet space.

Beautiful garden cabin

The Post Office Barn Chalgrove

14th Century Dairy

White Cottage Annexe with riverside garden hot tub

Garden Pavilion
Quick stats about guesthouse rentals in Windsor and Maidenhead
Total rentals
80 properties
Total number of reviews
4.8K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wifi availability
80 properties include access to wifi
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- Guesthouse rentals Berkshire
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- Guesthouse rentals United Kingdom
- British Museum
- Covent Garden
- Green Park
- Buckingham Palace
- Big Ben
- Lord's Cricket Ground
- Tower Bridge
- London Bridge
- Wembley Stadium
- Harrods
- The O2
- Hampstead Heath
- Emirates Stadium
- ExCeL London
- Camden Market
- St Pancras International
- London Stadium
- Alexandra Palace
- Oxford University
- Clapham Common
- River Lee Navigation
- Blenheim Palace
- Goodwood Motor Circuit
- Queen Elizabeth Olympic Park, London
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
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- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes