Top Cottages in Windsor and Maidenhead in 2026

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Our top choices for Windsor and Maidenhead cottages

A rustic wooden room with a bed, a bench, and a view of greenery outside.

1. Charming Riverside Cottage - Ideal for Families & Groups, Pool, Gardens & River

Wraysbury

GEORGE W.

A cottage with a white door, a window with a curtain, and a sign that reads "THE COTTAGE".

2. Inclusive, child-friendly, dogs welcome, garden area, near pubs/river/golf

Cookham Dean

Helen H.

A traditional brick house with a gabled roof, surrounded by lush greenery and a large tree.

3. Gorgeous Country Cottage, beside Windsor Great Park & overlooking Windsor Castle

Old Windsor

"The Cottage was a great base for exploring Windsor, London and of course antique shopping. It was a quiet sanctuary after a long day and provided all of the amenities for a comfortable stay. The host was awesome and answered all of our questions. Traffic from the road was a bit noisy but not too bad. The garden was lovely and private with lots of charm and nature. Views from the house to Windsor Castle were beautiful. Location was great offering many dining and shopping options."

Mike and Peg H.

A two-story brick house with a covered patio, a wooden fence, and a grassy yard.

4. Thames Retreat

Wraysbury

HK$4,843 total

includes taxes & fees

15 Nov - 16 Nov

A modern living room with a sofa, two chairs, a dining table, and a kitchen area.

5. The Annex

Slough

A brick house with a tiled roof, a front door, and windows with lights on.

6. THE OLD SCHOOL HOUSE, ASCOT, BERKSHIRE

Ascot

Gemma

A round table with chairs on a balcony, surrounded by a lattice fence, with a view of trees and greenery.

7. A magical and romantic getaway near Windsor Castle and beside Windsor Great Park

Old Windsor

Laura W.

A modern living room with a grey sofa, a dark rug, and a staircase leading to an upper floor.

8. Charming 2 Bed Cottage in Windsor - By Tempstay

Clewer North

"There is no parking at the property. It’s pot luck on roads around the property!! I received a parking ticket during my stay having specifically booked because the listing said parking. The beds were really comfortable, but some of the cleanliness and condition of things was questionable. There’s also a really noisy neighbour who blares television through the wall until 12pm. Shame, it had so much potential."

Marion A.