24/7 “On Holiday” Support

Our friendly UK team are here to help, in case of any emergency.

Award Winning Holiday Experts

Over 30 years of experience in UK self-catering holidays.

B Corp Certified Business

Committed to making a positive social and environmental impact.

Safe & Secure Payments

Flexible payment options for peace of mind.

Cottages Near Legoland Windsor

REFINE SEARCH

Your Windsor, Windsor and Maidenhead search returned 285 cottages

Most relevant
  • Distance to Location
  • Most relevant
  • Price (lowest first)
  • Price (highest first)
  • Sleeps (lowest first)
  • Sleeps (highest first)
  • Tick Rating (lowest first)
  • Tick Rating (highest first)
  • Guest Rated (highest first)
20
  • 10
  • 20
  • 50
  • 100
  • 8 Guests
  • 4 Bedrooms
  • Pets Yes

    Sykes Rating

A pretty, four-bedroom cottage nestled into the village of Blewbury, Oxfordshire. Open fire. Garden. Pet-friendly. Didcot 4.2 miles; Reading 15.9 miles; Oxford 18.5 miles. (Ref. 1136387)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £663

  • 6 Guests
  • 3 Bedrooms
  • Pets No

    4.4

    Sykes Rating

A light and airy, second-floor apartment settled in Littlehampton, West Sussex. Near beach. Swimming pool. Gym. Bognor Regis 7.8 miles; Chichester 13.2 miles; Brighton 20.1 miles. (Ref. 1112832)

  • Wi-fi
  • Off-road parking
  • Swimming pool
  • Baby-friendly

7 nights from £446

  • 2 Guests
  • 1 Bedroom
  • Pets Yes

    3.9

    Sykes Rating

Thames Retreat, a lovely annex situated in the beautiful village of Wraysbury, Berkshire. Couple's retreat. Peaceful location. Close to amenities. Windsor 4.9 miles; Maidenhead 13.1 miles; London 22.7 miles. (Ref. 1151367)

  • Wi-fi
  • Off-road parking

7 nights from £485

  • 4 Guests
  • 2 Bedrooms
  • Pets Yes

    Sykes Rating

Holly is a delightful, pet-friendly holiday home resting in the small hamlet of Elcot near Knitbury in Berkshire with a single-storey living space. Newbury 6.6 miles; Swindon 20.6 miles; Reading 23.3 miles. (Ref. 1167305)

  • Wi-fi
  • Off-road parking
  • Swimming pool
  • Ground floor bedroom
  • Dishwasher

7 nights from £596

  • 4 Guests
  • 2 Bedrooms
  • Pets Yes

    Sykes Rating

Rowan is a charming, single-storey holiday home situated in the small hamlet of Elcot near Knitbury in Berkshire, boasting an open-plan living space. Newbury 6.6 miles; Swindon 20.6 miles; Reading 23.4 miles. (Ref. 1167306)

  • Wi-fi
  • Off-road parking
  • Swimming pool
  • Ground floor bedroom
  • Dishwasher

7 nights from £628

  • 6 Guests
  • 3 Bedrooms
  • Pets Yes

    Sykes Rating

3 Malthouse Cottages is a characterful Grade-II listed home sitting pretty in the South Downs National Park in Chawton near Alton, near to a pub. Four Marks 3.4 miles; Bordon 7.8 miles; Portsmouth 29.3 miles. (Ref. 1167530)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • 10% off - Tue 18th Mar to 31st May 2025

7 nights from £865

  • 2 Guests
  • 1 Bedroom
  • Pets Yes

    4.5

    Sykes Rating

This wonderful ground-floor studio apartment rests on the outskirts of Paddock Wood, Kent. Pet-friendly. Off-road parking. Open-plan. Maidstone 8.7 miles; Tonbridge 9 miles; Royal Tunbridge Wells 9.9 miles. (Ref. 1080904)

  • Off-road parking
  • Ground floor bedroom
  • Baby-friendly

7 nights from £397

Last booked 2 days ago
See more details
  • 5 Guests
  • 3 Bedrooms
  • Pets No

    4.2

    Sykes Rating

This charming three-bedroom holiday home rests in Havant, Hampshire. Pet-friendly. Enclosed garden. Off-road parking. Waterlooville 4.8 miles; Portsmouth 8.6 miles; Chichester 9.9 miles. (Ref. 1121678)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine

7 nights from £493

  • 4 Guests
  • 1 Bedroom
  • Pets No

    Sykes Rating

Spindle is a cheerful, single-storey shepherd's hut set on the outskirts of South Leigh, Oxfordshire, boasting a woodburning stove and countryside views. Oxford 12.5 miles; Bibury 21.5 miles; Stow-on-the-Wold 19.9 miles; Bourton-on-the-Water 24 miles. (Ref. 1167989)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Ground floor bedroom
  • Dishwasher

7 nights from £399

  • 6 Guests
  • 2 Bedrooms
  • Pets No

    Sykes Rating

Windsurfer’s Rest is a pleasing, single-storey lodge located within a holiday park on Hayling Island, Hampshire, only a short walk to a pub and beach. Havant 4.5 miles; Emsworth 6.5 miles. (Ref. 1169541)

  • Wi-fi
  • Off-road parking
  • Swimming pool
  • Ground floor bedroom
  • Baby-friendly
  • 10% off - Fri 4th Apr to 2nd May 2025

7 nights from £340

  • 2 Guests
  • 1 Bedroom
  • Pets No

    Sykes Rating

Ground Floor Annexe, a quaint cottage resting in the charming village of Milton-under-Wychwood, Oxfordshire. In the Cotswolds AONB. Electric fire. Burford 4 miles; Chipping Norton 7.9 miles. (Ref. 1156529)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £446

  • 4 Guests
  • 1 Bedroom
  • Pets No

    Sykes Rating

Hazel is a lovely, single-storey shepherd's hut situated on the outskirts of South Leigh, Oxfordshire, with a woodburning stove and countryside views. Oxford 12.5 miles; Bibury 21.5 miles; Stow-on-the-Wold 19.9 miles; Bourton-on-the-Water 24 miles. (Ref. 1167984)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Ground floor bedroom

7 nights from £405

  • 3 Guests
  • 1 Bedroom
  • Pets Yes

    Sykes Rating

Galley Hill Garden Studio is a wonderful, single-storey cottage located in Selborne near Bordon, Hampshire, enjoying the countryside and welcoming one pet. Farnham 13.1 miles; Haslemere 12.6 miles; Winchester 17.9 miles; Chichester 23.9 miles. (Ref. 1151770)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Ground floor bedroom

7 nights from £507

  • 6 Guests
  • 2 Bedrooms
  • Pets No

    Sykes Rating

Blue Flag Shores is a wonderful, single-storey property set on Hayling Island in Hampshire, boasting close proximity to a beach and National Park. Havant 4.5 miles; Emsworth 6.5 miles. (Ref. 1169547)

  • Wi-fi
  • Off-road parking
  • Swimming pool
  • Ground floor bedroom
  • Baby-friendly
  • 10% off - Fri 4th Apr to 2nd May 2025

7 nights from £402

  • 6 Guests
  • 3 Bedrooms
  • Pets Yes

    Sykes Rating

Pebble House is a charming, three-bedroom dwelling perched in Worthing, West Sussex. Close to amenities and a beach. Pet-friendly. Sea views. Enclosed garden. Shoreham-by-Sea 6.8 miles; Brighton and Hove 12.9 miles; Chichester 19.6 miles. (Ref. 1134133)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £601

  • 4 Guests
  • 2 Bedrooms
  • Pets Yes

    Sykes Rating

RiverGem - Riverside Coach House is a lovely, pet-friendly first-floor apartment situated in the historic city of Winchester in Hampshire near amenities. Southampton 12.3 miles; North Wessex Downs AONB 13.4 miles; Basingstoke 18.8 miles. (Ref. 1012228)

  • Wi-fi
  • Off-road parking

7 nights from £612

  • 6 Guests
  • 2 Bedrooms
  • Pets No

    Sykes Rating

Billy’s Way is a spacious, single-storey caravan on the Hayling Island Holiday Park in Hampshire, boasting only a short walk to a pub, shop, and beach. Havant 4.5 miles; Emsworth 6.5 miles. (Ref. 1169544)

  • Wi-fi
  • Off-road parking
  • Swimming pool
  • Ground floor bedroom
  • Baby-friendly
  • 10% off - Fri 4th Apr to 2nd May 2025

7 nights from £429

  • 4 Guests
  • 2 Bedrooms
  • Pets Yes

    4.9

    Sykes Rating

A stunning single-storey barn conversion resting in Beauworth near Cheriton, Hampshire. Original features. Pet-friendly. Open-plan. Woodburning stove. In National Park. New Alresford 4.1 miles; Winchester 7.9 miles; Southampton 15.7 miles. (Ref. 1119351)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from £768

  • 7 Guests
  • 4 Bedrooms
  • Pets Yes

    Sykes Rating

The Stables, a stylish detached house nestled in the village of Cuddesdon in Oxfordshire. Luxury interior. Enclosed garden. Pet-friendly. Off-road parking. Oxford 8.7 miles; Aylesbury 18.6 miles (Ref. 1135009)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from £2093

  • 4 Guests
  • 2 Bedrooms
  • Pets Yes

    Sykes Rating

Dutch 2 is a romantic barn conversion resting near the market town of Lechlade-On-Thames in Oxfordshire with private driveway parking and enclosed patio. Cirencester 14.8 miles; Oxford 26.1 miles. (Ref. 1166925)

  • Wi-fi
  • Off-road parking

7 nights from £664